MLB Trades: Power Ranking the 50 Biggest Rip-Offs in League History

Trades are a funny thing.

They are a part of every sport, and the one common characteristic that can describe their nature is their inherent volatility. Trades can be a savior to teams, bringing them to the pinnacle of success. Or they can be the perpetual oppressor, blamed by fans for years of struggle and hardship. Sometimes, the same trade can be viewed either way, depending on the point of view of the fan.

No sport has such a voluminous history of transactions as America's pastime, so it's no surprise that deciding which were the absolute worst was no small task.

Think I have anything out of place or that I haven't included a trade that deserved to be on here? Let me know.

50) Mariners Trade Shin-Soo Choo To Cleveland For Ben Broussard

July 26, 2006

Full Details: Seattle Mariners trade OF Shin-Soo Choo and a player to be named later (P Shawn Nottingham) to the Cleveland Indians for 1B/OF Ben Broussard and cash

This deal has the potential to quickly move up the rankings of worst trades of all-time.

Broussard played just 155 games over one-and-a-half seasons with the Mariners and he was fairly terrible. He was traded to the Rangers following the ’07 season and appeared in just 26 games while batting just .159 in 2008. He’s been out of baseball ever since.

Choo, however, has developed into one of the best, yet least known, players in baseball. Only 28 years of age, the South Korean native has been one of the few bright spots for the Indians over the last three seasons. Choo has hit right around .300/.395/.485 and has 42 home runs, 176 RBI, and 43 stolen bases over the last two seasons. If a thumb injury hadn’t caused him to miss 18 games while limiting his power upon returning, Choo might have had a legitimate shot at 30-100-20 in 2010.

49) Andre Ethier For Milton Bradley

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December 13, 2005

Full Details: Oakland Athletics trade OF Andre Ethier to Los Angeles Dodgers for OF Milton Bradley and INF Antonio Perez

After winter meetings had come to a close, the Los Angeles Dodgers made it clear that they were shopping Bradley hard.

Bradley had shown displays of talent during stops in both Montreal and Cleveland, but questions of attitude have followed him throughout his career.

Bradley hit .279 over parts of 2006 and 2007. He was designated for assignment by the A’s in June of ’07, and he was later traded to the Padres.

Bradley is still what he was at the time of the trade—a player with some significant talent and a rather large attitude problem, who hasn’t been able to put it together during his time in the big leagues.

Ethier, however, has become one of the best young players in baseball. His clutch bat has led the Los Angeles Dodgers over the past five seasons. Despite experiencing injuries in 2010, Ethier is still entering his prime (currently age 28), and he has the potential to become one of the best players in the game.

48) Kansas City Royals Trade Lou Piniella For Lindy McDaniel

December 7, 1973

Full Details: Kansas City Royals trade OF Lou Piniella and P Ken Wright to the New York Yankees for P Lindy McDaniel

Piniella would go on to play 11 seasons of baseball (1974-84) with the Yankees before retiring.  He was an integral part of the Yankees appearing in three straight World Series’ from 1976-78, including two wins in ’77 and ’78. In 44 career postseason games and 141 at-bats with the Yankees, Piniella hit .305.

McDaniel would appear in 78 games over two seasons with the Royals (1974-75), mostly out of the bullpen. He was mediocre, posting a combined 3.75 ERA, and he retired after the ’75 season.

47) Pittsburgh Pirates Trade Jason Schmidt To San Francisco Giants

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July 30, 2001

Full Details: Pittsburgh Pirates trade P Jason Schmidt and OF/1B John Vander Wal to the San Francisco Giants for OF Armando Rios and P Ryan Vogelsong

Schmidt had a pretty good run as a member of the Giants from 2001-2006. In 2003, Schmidt went 17-5, leading the National League in both ERA (2.34) and WHIP (0.953). He fanned 208 batters, made his first All-Star game, and finished second in Cy Young voting.

The following season, Schmidt was 18-7 with a 3.20 ERA, 1.08 WHIP, and 251 strikeouts. He was again an All-Star and finished fourth in Cy Young voting.

Rios played in just 78 games over two seasons with the Pirates (2001-02).

In four seasons with Pittsburgh (2001, 2003-06), Vogelsong went a combined 10-19 with a 6.13 ERA over 101 appearances. How he lasted that long, I’ll never know, but he was out of baseball following the 2006 season.

46) Mets Trade Lenny Dykstra To Phillies For Juan Samuel

June 18, 1989

Full Details: New York Mets trade OF Lenny Dykstra, P Roger McDowell, and a player to be named later (P Tom Edens) to the Philadelphia Phillies for 2B/OF Juan Samuel

This is one of the many poor trades that still haunt Mets fans.

Samuel was a good hitter for the Phillies in the early-to-mid 80s, and his 28 home runs, 100 RBI season in 1987 was fresh in the baseball world’s mind.

However, Samuel would play just 86 games for the Mets in 1989, hitting just .228 with three home runs and 28 RBI. In December of ’89, he was traded from the Mets to the Dodgers. Samuel played until 1998, with stops in Kansas City, Cincinnati, Detroit, and Toronto after leaving Los Angeles in 1992. He was never the same hitter he was in the early part of his career.

When healthy, Dykstra enjoyed a productive career over eight seasons with the Phillies (1989-96). He batted over .300 in three seasons with Philly (1990, 1992-93), and led the NL in hits in 1990 and 1993. He was also a three time All-Star (1990, 1994-95).

McDowell was a reliable reliever for the Phillies who appeared in 154 games over parts of three seasons (1989-91). He saved 44 games for Philadelphia over this period.

45) Orioles Trade Roy Sievers To The Washington Senators For Gil Coan

February 18, 1954

Full Details: Baltimore Orioles trade 1B/OF Roy Sievers to the Washington Senators for OF Gil Coan

Coan played in just 61 games for the Orioles in 1955, hitting just .238. He was claimed by the White Sox on waivers in July and played just 30 more games before retiring.

Sievers became one of the league's best power hitters and had 275 home runs and 1,029 RBI over a 10-year span (1954-1963) with the Senators, White Sox, and Phillies. He was a four-time All-Star over this stretch (1956-57, 1959, 1961). In 1957, Sievers led the the American League with 42 home runs and 114 RBI, finishing third in MVP voting.

44) Rangers Trade Mark Teixeira For Neftali Feliz and Elvis Andrus

July 31, 2007

Texas Rangers trade 1B Mark Teixeira and P Ron Mahay to the Atlanta Braves for SS Elvis Andrus, P Neftali Feliz, C Jarrod Saltalamacchia, P Matt Harrison, and P Beau Jones

The Atlanta Braves were in third place at the 2007 trading deadline, but they were just 3.5 games behind the division leading New York Mets.

The Braves figured that they had a good shot at making a deep postseason run, so when they brought in first baseman Mark Teixeira from the Texas Rangers, things were looking good.

The Braves gave up three top prospects for “Tex”: catcher Jarrod Saltalamacchia, right-hander Neftali Feliz, and shortstop Elvis Andrus. While “Salty” is no longer with the Rangers, Neftali Feliz and Elvis Andrus have both blossomed into young stars. Both were key parts of the AL pennant-winning 2010 Texas team, and both should help keep the Rangers relevant for the foreseeable future.

However, despite solid production from Teixeira, the Braves were unable to make the postseason, finishing five games behind eventual division-winning Philadelphia Phillies. The following season, the Braves finished 72-90, again failing to qualify for the playoffs.

After the 2008 season, Mark Teixeira was able to translate his career success into an eight-year, $180-million deal with the New York Yankees. The Braves essentially got a year-and-a-half of productive, yet meaningless, play, as they weren’t able to retain the slugger or make the postseason.

However, in 2010, Feliz saved 40 games—a rookie record—was an All-Star, and won the Rookie of the Year award.

Andrus has been the Rangers starting shortstop for two years now. At just 23 years of age, he’s shown ability as a baserunner, fielder, and hitter. With shortstop one of the thinner positions in the majors, Andrus has the ability to become one of the best in the game.

43) Marlins Trade Derrek Lee To Cubs For Hee-Seop Choi

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November 25, 2003

Full Details: Florida Marlins trade 1B Derrek Lee to Chicago Cubs for 1B Hee-Seop Choi and P Mike Nannini

At the time of the deal, South Korean native Hee-Seop Choi was considered one of the top minor-league prospects in the Chicago Cubs organization.

Derrek Lee was a 27-year-old first baseman who had quietly amassed some very decent stats. Over four straight seasons (2000-03) with the Marlins, Lee averaged 27 home runs per year. In each season, his OPS was well above .800. He even turned himself into a reliable first baseman and captured his first Gold Glove in 2003.

The Marlins won the NL pennant in ’03, and beat the Yankees in six games in the World Series, capturing their second title just 11 years after coming into the league as an expansion team.

Yet the Marlins felt inclined to trade Lee following the 2003 season, as he was deemed a necessary sacrifice in order to keep the Marlins cost-efficient budget intact.

Following the trade, Lee was very good for the Cubs in 2004. He finished with 32 home runs, 98 RBI, and 12 stolen bases. He also hit .278/.356/.504.

In 2005, Lee had perhaps the best year of his career. He exploded for 46 home runs and 107 RBI, and led the NL in hits (199), doubles (50), batting average (.335), slugging percentage (.662), and OPS (1.080). He was an All-Star, won his second Gold Glove and first Silver Slugger award, and finished third in MVP voting.

Lee continued to be one of the better first baseman in the game when healthy and he spent six-and-a-half total seasons with the Cubs, when he was traded to the Atlanta Braves during the 2010 season.

Choi, however, never quite lived up to his billing. He appeared in 95 games before the Marlins traded him to the Dodgers at the 2004 trading deadline. Choi played in 133 games for the Dodgers in 2005, and he hasn’t appeared in a major-league game since that year. He’s now playing in the KBO (Korean Baseball Organization).

42) Pirates Trade Aramis Ramirez, Kenny Lofton To Chicago Cubs

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July 23, 2003

Full Details: Pittsburgh Pirates trade 3B Aramis Ramirez, OF Kenny Lofton, and cash to the Chicago Cubs for P Matt Bruback, INF Jose Hernandez, and a player to be named later (INF Bobby Hill)

Kenny Lofton was already an established veteran when he came to Chicago via trade in 2003. While he would stay for just the remainder of the season, he was instrumental in the team’s success that year.

In 56 regular-season games, Lofton would hit .327/.381/.471, steal 12 bases, and score 20 runs. He would bat .286 with six hits and three runs scored in the NLDS and hit .323 with 10 hits and eight runs in the NLCS, which the Cubs infamously lost in seven games to the Florida Marlins.

Ramirez has played his entire career since the trade with the Cubs, and he has given them 213 home runs and 713 RBI, while batting .293/.355/.534 over seven-and-a-half seasons (2003-10). When healthy, Ramirez still remains one of the best-hitting third baseman in the game.

Bruback never appeared in a major-league game, and Hill and Hernandez both had inconsequential careers with the Cubs. Neither has appeared in a major-league game since 2006.

41) Red Sox Trade Sparky Lyle To The New York Yankees For Danny Cater

March 22, 1972

Full Details: Boston Red Sox trade P Sparky Lyle to the New York Yankees for INF/OF Danny Cater and a player to be named later (INF Mario Guerrero)

The first year after the trade, Lyle saved 35 games for the Yankees, finishing seventh in Cy Young voting and third in MVP voting.

Lyle would go on to save 141 games for the Yankees over eight seasons (1972-78), which included three All-Star appearances (1973, 1976-77) and one Cy Young award (1977).

Cater would hit just .262 over three seasons with the Red Sox (1972-74) and averaged just 70 games per year. Guerrero would hit just .225 over two seasons with the Sox (1973-74).

40) Rangers Trade Adrian Gonzalez To San Diego For Adam Eaton/Akinori Otsuka

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January 6, 2006

Full Details: Texas Rangers trade 1B Adrian Gonzalez, OF Terrmel Sledge, and P Chris Young to the San Diego Padres for P Adam Eaton, P Akinori Otsuka, and Billy Killian

First off, I’d just like to point out how awesome a name Terrmel Sledge is. I mean really, it doesn’t get much better than that, folks.

Since this trade, Adrian Gonzalez has developed into one of the best hitters and defensive first baseman in the game. He’s a career .284/.368/.507 hitter, with 168 home runs and 525 RBI. He brings a rare blend of power and patience to the plate, as well as one of the best opposite-field strokes in the game. He’s been an All-Star over the last three seasons (2008-10), and a two-time Gold Glove winner (2008-09). Gonzo is a free agent after the 2011 season, and even if the Padres can’t resign him, he’ll likely make them prospect rich at the trading deadline (unless, of course, they screw up and trade him for a bunch of busts. Then that trade will be on one of these lists 25 years from now).

Young’s 2011 option was declined by the Padres, despite the fact that he pitched well down the stretch last season after missing nearly five months with injury. Young is 30 and he has been decent at times over his MLB career, so it remains to be seen where exactly he’ll end up.

Killian has never appeared in a MLB game. Eaton was just 7-4 with a 5.12 ERA in his lone year in Texas (2006), and he is no longer with any MLB organization.

Otsuka was actually very good in his two years with Texas (2006-07). He went 4-5 with a combined 2.25 ERA in 97 games out of the bullpen, while registering 36 total saves in the absence of Francisco Cordero and Eric Gagne. However, elbow surgery has since forced him out of the game.

Imagine if A-Gon was the first baseman in the current incarnation of the Rangers? (Gulp) Can you say World Series championship?

39) Mets Trade Jeff Kent To Indians For Carlos Baerga

July 29, 1996

Full Details: New York Mets trade 2B Jeff Kent and INF Jose Vizcaino to the Cleveland Indians for 2B Carlos Baerga and INF Alvaro Espinoza

The main players in this one were Kent and Baerga.

Kent was a 28 year old who never reached his full potential over four-and-a-half seasons with the New York Mets (1992-96). Baerga was a 27 year old who, already in his seventh major-league season, had been a three time All-Star (1992-93, 1995) and a two-time Silver Slugger (1993-94).  He had posted a batting average of .300 or above and an OPS of .800 or above from 1992-95.

In a swift reversal of fortune, Baerga quickly became the one to not live up to his potential while Kent became one of the best players in the game in the late ‘90s and early 2000s.

Baerga hit a total of 18 home runs and 116 RBI, and batted just .267/.302/.373 over his two-and-a-half seasons in New York (1996-98).

While Kent played only 39 games with the Cleveland Indians in 1996, he went on to have a very good career with the Giants, Astros, and Dodgers. He was a five-time All-Star (1999-2001, 2004-05), four-time Silver Slugger (2000-02, 2005), and a one-time National League MVP—with the Giants in 2000. He hit 20 or more home runs in 10 seasons after the trade, and eclipsed 30 home runs three times during that span. He finished his career a .290/.356/.500 hitter, with 377 home runs, 1,518 RBI, and 2,461 hits.

38) Cardinals Trade Keith Hernandez To New York Mets For Allen and Ownbey

June 15, 1983

Full Details: St. Louis Cardinals trade 1B Keith Hernandez to the New York Mets for P Neil Allen and P Rick Ownbey

After frequent clashes with manager Whitey Herzog, Hernandez was finally dealt from St. Louis during the 1983 season.

Hernandez hit .306/.424/.434 over the remaining 95 games with the Mets, and captured his sixth consecutive Gold Glove.

He went on to play another six seasons in a Mets uniform and, over that period, was elected to three All-Star games (1984, 1986-87), won five more Gold Gloves (1984-88), was in the top 10 in MVP voting from 1984-86 (including a second-place finish in ’84), and even won a Silver Slugger (1984).

Despite being one of the better closers in the game from 1979-1982, Allen struggled mightily with the Cardinals. In 1983, Allen was converted to a starter and went 10-6 with a 3.70 ERA. He was converted back to a reliever in 1984, when he made just 57 appearances, with just one save. Allen was sold to the New York Yankees during the 1985 season.

Ownbey isn’t much more than a footnote in history: He appeared in four games with the Cards in 1984 and 17 in 1986. He never appeared in a big-league game after that.

37) Astros Trade Freddy Garcia/Carlos Guillen For Randy Johnson

July 31, 1998

Full Details: Seattle Mariners trade P Randy Johnson to the Houston Astros for P Freddy Garcia, INF Carlos Guillen, and P John Halama

Johnson was spectacular for the Astros in 1998. He went 10-1 with a 1.28 ERA in 11 starts. However, despite posting a 1.93 ERA in the playoffs that year, Johnson was 0-2 and the Astros were eliminated by the Padres in the ALDS. That was it. Johnson left town for a large contract with Arizona.

Meanwhile, Garcia went 76-61 over five-and-a-half seasons with the Mariners (1999-2004), and he was considered to be one of the better pitchers in the league during his time in Seattle.

Guillen was never fantastic in Seattle, but he had some great years with Detroit in the middle part of the decade. Recently, injuries have hit Guillen hard. He’s a three-time All-Star (2004, 2007-08), and a career .286/.357/.445 hitter.

If Johnson had stayed in Houston, this would be an entirely different story, but half-a-season of very good, yet fruitless, production doesn’t justify this trade.

36) Blue Jays Trade Michael Young To Texas Rangers For Esteban Loaiza

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July 19, 2000

Full Details: Toronto Blue Jays trade 2B/SS/3B Michael Young and P Darwin Cubillan to Texas Rangers for P Esteban Loaiza

Looking to bolster their pitching staff, the Blue Jays sent then 23-year-old infielder Michael Young and reliever Darwin Cubillan to Texas in return for starter Esteban Loaiza.

Loaiza wasn’t good over two-and-a-half seasons in Toronto (2000-02). He was just a combined 25-28 with a 4.96 ERA. A free agent after the ’02 season, Loaiza signed a minor-league contract with the Chicago White Sox. Loaiza then went on to have the best year of his career, going 21-9 with a 2.90 ERA and 1.11 WHIP. He would also lead the American League in strikeouts (207), and finish second in Cy Young voting, behind only former teammate Roy Halladay.

Michael Young, however, has been one of the most consistent performers in baseball ever since his first full season with Texas in 2001. He spent time at second base early in his career, played the bulk of his career at short, and he has made the transition to third seamlessly, in order to make room for young star Elvis Andrus. He’s the longest-tenured Ranger, and he is considered one of the best team players in the sport.

And on top of all that, he’s got pretty good numbers. Young was an All-Star for six consecutive seasons from 2004-2009, and a Gold Glove winner in 2008, his last year at shortstop. He’s a career .300/.347/.448 hitter, and he has four seasons of 20 or more home runs to his name. In 2005, he led the American League in hits (221) and batting average (.331). He finished 11th in MVP voting that year, and has finished as high as eighth in 2004. His 1,848 career hits are first all time in Texas Ranger history and he should move into first place in games played after the 2011 season.

35) Tampa Bay Devil Rays Trade Bobby Abreu To Phillies For Kevin Stocker

November 18, 1997

Full Details: Tampa Bay Devil Rays trade OF Bobby Abreu to the Philadelphia Phillies for SS Kevin Stocker

After the Tampa Bay Devil Rays selected Bobby Abreu from the Houston Astros in the sixth round of the 1997 expansion draft, they traded him that very same day to Philadelphia for Kevin Stocker.

The Phillies got nearly eight-and-a-half years of service (1998-2006), a .303 batting average, 195 home runs, 814 RBI, 214 stolen bases and nearly 1,500 hits.

The Devil Rays got 231 games of MLB service over parts of three seasons (1998-2000). Stocker hit just .250 and he has been out of baseball since 2000.

Abreu was one of the biggest 30-30 threats in his day while Stocker was a huge bust.

The Rays toiled in the bottom of the AL East until 2008 when they made it to the World Series and lost, ironically enough, to the Phillies.

34) Kansas City Athletics Trade Roger Maris To New York For Norm Siebern

December 11, 1959

Full Details: Kansas City Athletics trade OF Roger Maris, INF Joe DeMaestri, and 1B Kent Hadley to the New York Yankees for 1B/OF Marv Thornberry, 1B/OF Norm Siebern, P Don Larsen, and OF Hank Bauer

There are a lot of names involved in this deal, so let me make it pretty clear. In this trade, Roger Maris was sandwiched between mostly junk, busts, and aging players. Other than Norm Siebern and, obviously, Maris, everyone in this trade had either peaked or wouldn’t do anything of any significance in the majors.

Siebern had four decent seasons with the A’s from 1960-63, including his 1962 line of 25 home runs, 117 RBI, and .308/.412/.495. After the 1963 season, he was traded to the Orioles, where he would slowly fade into obscurity.

Maris, on the other hand, would win consecutive MVP’s in 1960 and 1961. His then record-breaking 61 homer season in ’61 remains one of the most heavily-profiled seasons in baseball history.

Maris remained a decent ballplayer until he was hit hard by injuries in 1965 and again in 1966. Following the ’66 season, he was traded to the St. Louis Cardinals, where he played two more seasons before retiring.

33) Cardinals Trade Ray Sadecki To San Francisco Giants For Orlando Cepeda

May 8, 1966

Full Details: St. Louis Cardinals trade P Ray Sadecki to the San Francisco Giants for 1B/OF Orlando Cepeda

Sadecki had been an on-again, off-again good pitcher for his career when he was dealt to the Giants during the 1966 season. He went just 3-7 with a 5.40 ERA in 19 games with the Giants. In 1967 he righted the ship and went 12-6 with a 2.78 ERA and 1.19 WHIP, even though he managed just 24 starts. In 1968, Sadecki had a 2.91 ERA and 1.16 WHIP, yet led the National League in losses (18, as compared to just 12 wins).

Sadecki would play just one more mediocre season before being traded to the Mets in December of 1969.

Cepeda hit just .176 in an injury-filled 1965 with the Giants, but redeemed himself with the Cardinals. In 123 games for St. Louis in 1966, Cepeda hit 17 home runs and 58 RBI, with a .303/.362/.469 batting line. In 1967, Cepeda had 25 home runs and 111 RBI (which led the NL), while batting .325/.399/.524. He would go on to win the National League MVP that year, and lead his Cardinals to a seven-game World Series victory over the Boston Red Sox.

32) Tommy John Sent to White Sox From Cleveland As Part Of 3-Team Deal

January 20, 1965

Full Details: Cleveland Indians send P Tommy John, OF Tommie Agee, C John Romano to Chicago White Sox. Chicago White Sox send C Cam Carreron to the Cleveland Indians; player to be named later (P Fred Talbot), OF Mike Hershberger, and OF Jim Landis to the Kansas City Athletics. The A’s send OF Rocky Colavito to the Cleveland Indians.

While Tommy John is most known for his post-surgery career with the Dodgers and Yankees, he was still a good pitcher with the White Sox. Despite having a record of 82-80 in his career with the White Sox, he also had a 2.95 ERA and 1.18 WHIP over those same seasons. One has to take into account the fact that the White Sox were almost always near the bottom of the league in runs scored from 1965-71.

In 1966, Agee was an All-Star and Rookie of the Year winner. He hit 22 home runs and 86 RBI, batting .237/.326/.477.

Romano did little on the major-league level, but neither did Carreron, Talbot, Hershberger and Landis (after 1966 at least).

31) Padres Trade Ozzie Smith To St. Louis For Gary Templeton

December 10, 1982

Full Details: San Diego Padres trade SS Ozzie Smith, P Steve Mura and a player to be named later (P Al Olmsted) to St. Louis Cardinals for SS Gary Templeton, OF Sixto Lezcano and a player to be named later (P Luis DeLeon)

In what is now remembered as a steal of a deal for the St. Louis Cardinals, the San Diego Padres sent shortstop Ozzie Smith to St. Louis in return for shortstop Gary Templeton.

What’s interesting about this deal is that, at the time, it looked like the Padres were the one pulling the fleece over the Cardinals eyes, not vice versa.

Templeton was more than a year younger than Smith and, to that point in his career, had been a much better player. At the time of the trade, Templeton surpassed Smith in virtually every offensive category except stolen bases, which Smith had the slight edge on (147 career SB’s to 138).

In fact, the Cardinals were not trading Templeton on any performance-based issues. Rather, manager Whitey Herzog had had enough of the young shortstop, who had become a clubhouse distraction. In 1981, Templeton had been suspended for making obscene gestures at Cardinals fans. By the time of the trade, both sides were glad to leave the other behind.

Unfortunately for Templeton, a rash of knee injuries diminished his offensive abilities. Also, Smith was able to improve his offensive skills while maintaining his defensive prowess (13 straight Gold Glove awards from 1980-92).

While Templeton was no slouch at the plate after the deal, Smith’s increased offensive skills and glove wizardry clearly made him the better overall player. Smith also lasted five more seasons than Templeton, despite being older.

The deal is now remembered as one of the biggest steals in recent history.

30) Jay Buhner For Ken Phelps

Phelps (left); Buhner (far right)

 July 21, 1988

Full Details: New York Yankees trade OF Jay Buhner and a player to be named later (Troy Evers) with Rich Balabon to the Seattle Mariners for 1B/DH Ken Phelps 

“What the hell did you trade Jay Buhner for? He had 30 home runs, over 100 RBI’s last year. He’s got a rocket for an arm…you don’t know what the hell you’re doing!”

The Buhner-for-Phelps trade ended up so bad that even the fictional George Costanza had to offer a piece of his mind to the fictional George Steinbrenner on an episode of Seinfeld.

At the time of the trade, Buhner was a 23 year old with just 32 games of major-league experience under his belt. Phelps was a 34-year-old full time DH, who had never played more than 55 games in the field in any one season. Offensively, he was about a .240 career hitter, even though he was a patient hitter who did walk quite frequently.

Phelps hit just .240 with 17 home runs and 51 RBI over parts of two seasons with the Yankees (1988-89).

Buhner, however, blossomed into one of the better hitters in the game. He finished his career with 310 homers and 965 RBI. Over a three-year span from 1995-97, Buhner compiled 124 homers and 368 RBI, finishing with 40-plus homers and 100-plus RBI each season. He remains one of the greatest Seattle Mariners in history.

29) Red Sox Trade Curt Schilling and Brady Anderson To Baltimore Orioles

July 29, 1988

Full Details: Boston Red Sox trade P Curt Schilling and OF Brady Anderson to Baltimore Orioles for P Mike Boddicker

The trades that sent Schilling to Philadelphia and to Arizona are often highly profiled as some of the biggest gaffes in baseball history. Indeed, both appear on this list.

But the little-known deal that sent Schilling to Baltimore in the first place might be the worst of them all.

In the short term, the trade was a good one for the Red Sox. In 1988, Boddicker went 7-3 over 14 starts with a 2.63 ERA. The Sox won the East Division by one game over the Detroit Tigers after coming in fifth the year prior. However, they were swept in the ’88 ALCS by the Oakland Athletics. Boddicker gave up six earned runs over just 2.2 innings pitched in his only playoff start.

In 1990, Boddicker went 17-8 with a 3.36 ERA, and the Red Sox won the East by two games over the Toronto Blue Jays, after finishing third in 1989. However, the Red Sox were again swept by the Oakland Athletics in the ALCS.

Boddicker left as a free agent following the 1990 season and he spent two years with the Kansas City Royals and one with the Milwaukee Brewers before retiring.

Despite the questions surrounding Anderson and steroids, there’s no question that he was a pretty good player on or off the juice. No formal allegations of PED usage have ever come to light, despite rampant suspicion, due mostly to his anomalous 50 homer year in 1996.

Schilling eventually grew into one of the best pitchers in the game and spent very good years with the Phillies, Diamondbacks, and, eventually, the Red Sox again.

Despite the lopsided talent involved in this deal, the Red Sox get some points for reacquiring Schilling just in time for their 2004 World Series title. The way baseball goes, it’s highly unlikely that the Sox would have held onto Schilling long enough for him to be around in 2004. I’m sure most Red Sox fans wouldn’t change the way this trade went down if given the chance.

28) Chicago White Sox Deal Sammy Sosa Across Town For George Bell

March 30, 1992

Full Details: Chicago White Sox trade OF Sammy Sosa and P Ken Patterson to the Chicago Cubs for OF George Bell

Sosa struggled for parts of two seasons with the Chicago White Sox, so when they acquired 1987 AL MVP George Bell for him in 1992, it looked like they were getting a pretty good deal.

In 1992, Bell had 25 homers and 112 RBI, yet only hit .255/.294/.418.

However, in 1993, Bell’s play was significantly hampered by injury, and he was released following the season. He subsequently announced his retirement from baseball.

Sosa went on to become one of the most feared power hitters in the game. His 609 home runs rank seventh all-time.

Ken Patterson played just one season with the Cubs. He was 2-3 with a 3.89 ERA and 1.63 WHIP in 32 games, 31 out of the bullpen.

27) Kansas City Royals Send David Cone To The New York Mets

March 27, 1987

Full Details: Kansas City Royals trade P David Cone and OF Chris Jelic to the New York Mets for C Ed Hearn, P Rick Anderson, and P Mauro Gozzo

Cone had appeared in just 11 games for the Royals, all in relief, before he was traded the following offseason to the Mets.

Ed Hearn appeared in a grand total of 13 games over two years with the Royals. He was out of baseball after the 1988 season.

Anderson also pitched in only 13 games from 1987-88, and he was out of baseball after that.

Gozzo never appeared in a game for the Royals, and pitched in just 48 games over parts of six seasons (1989-94) with four different teams.

Cone, however, went on to become one of the best pitchers in baseball. He finished his career 194-126 with a 3.46 ERA and 1.26 WHIP, and 2,268 strikeouts (22nd all-time). Cone captured five World Series rings, one with Toronto in 1992, and four with the Yankees in 1996 and 1998-2000. He was a five-time All-Star and one-time Cy Young award winner (1994). He also pitched the 16th perfect game in baseball history in 1999.

The Royals get some points for acquiring Cone again for two seasons (1993-94), but not enough to keep them off this list. His only Cy Young award came as a member of the Royals, although it came during the strike-shortened season of ’94.

26) Oakland Athletics Trade Mark McGwire To St. Louis

Otto Greule Jr/Getty Images

July 31, 1997

Full Details: Oakland Athletics trade 1B Mark McGwire to the St. Louis Cardinals for P T.J. Matthews, P Blake Stein, and P Eric Ludwick

Mark McGwire had already established himself as one of the best hitters in baseball when the A’s traded him at the 1997 deadline. Over the previous two seasons (1995-96), McGwire totaled 91 home runs and 203 RBI, including a 52 home runs, 113 RBI, .312/.467/.730 line the year prior.

However, the A’s had no wish to resign McGwire to a lengthy contract, as he was a free agent at the end of the year. They took the “logical” path, and opted to trade him before the season end, in order to get players in return.

If only the return had been any good.

Matthews appeared in 210 games out of the bullpen for the A’s in parts of five seasons (1997-2001). He was an often used, yet mediocre, reliever: 24-15 record, 4.78 ERA, 1.44 WHIP over his career with Oakland.

Stein started 20 games in 1998, his only year in Oakland. He was 5-9 with a 6.37 ERA and 1.60 WHIP.

Ludwick appeared in just six games in 1997, his only season with Oakland. In those six games, he managed to go 1-4 with an 8.25 ERA and 2.00 WHIP. Ludwick appeared in just 14 major-league games for two different teams over the next two seasons and was out of baseball after 1999.

What did the Cardinals get?

In five seasons, McGwire totaled 220 homers and 473 RBI, including his infamous 70 home run season in 1998.

25) New York Yankees Trade Willie McGee To St. Louis For Bob Sykes

October 21, 1981

Full Details: St. Louis Cardinals trade P Bob Sykes to the New York Yankees for OF Willie McGee

Bob Sykes had been mostly a journeyman through five MLB seasons (1977-81) with the Tigers and Cardinals. He never appeared in another major-league game, for the Yankees or anyone else, after the trade was completed.

McGee, on the other hand, would go on to win the 1985 National League MVP with the Cardinals. He was also a four-time All-Star (1983, 1985, 1987-88), a three-time Gold Glove winner (1983, 1985-86), and a two-time batting champion (1985, 1990). McGee was also a part of the 1982 World Series Cardinals team. He played a total of 18 seasons and was a career .295 hitter.

24) Ryne Sandberg For Ivan DeJesus

January 27, 1982

Full Details: Philadelphia Phillies trade 2B/3B Ryne Sandberg and SS Larry Bowa to the Chicago Cubs for SS Ivan DeJesus

Larry Bowa was a 35-year-old shortstop with declining abilities when he began asking for a long-term deal. Unwilling to grant him such, the Phillies found a trading partner in Chicago Cubs GM and former Phillies manager Dallas Green.

Bowa was sent, along with 21-year-old Ryne Sandberg, to the Cubs for Ivan DeJesus before the start of the ’82 season.

Bowa wasn’t the steal here: he hit just .247 over his three seasons with the Cubs.

Rather, it was Ryne Sandberg, who after becoming the regular second baseman in 1983, went on to become a 10-time All-Star (1984-93), nine-time Gold Glove winner (1983-91), seven-time Silver Slugger (1984-85, 1988-92), and one-time MVP (1984). Sandberg was inducted into the Hall of Fame in 2005.

DeJesus, on the other hand, went on to play just three mediocre seasons of baseball with the Phillies, before being traded on Opening Day, 1985, to the St. Louis Cardinals. He appeared in just 82 games over the remaining four seasons of his career.

23) Phillies Trade Curt Schilling to Arizona

July 26, 2000

Full Details: Philadelphia Phillies trade P Curt Schilling to the Arizona Diamondbacks for P Vicente Padilla, P Omar Daal, P Nelson Figueroa, and 1B/OF Travis Lee

The Diamondbacks have a World Series ring to thank for this one.

After nearly eight-and-a-half seasons in a Phillies uniform, Curt Schilling was traded to the Arizona Diamondbacks during the 2000 MLB season.

The D’Backs wouldn’t see the benefits until the following season, 2001. That year, Schilling went 22-6 with a 2.98 ERA, 1.08 WHIP and 293 strikeouts. He led the NL in wins (22), games started (35), complete games (6),and innings pitched (256.2). He was second in Cy Young voting, finishing behind teammate Randy Johnson.

The dynamic duo of Johnson and Schilling led the Diamondbacks to the World Series, where they captured the first title in franchise history.

Schilling was again phenomenal in 2002 and finished second in Cy Young voting, again to teammate Randy Johnson.

Padilla, however, appeared in 23 games as a reliever in 2001, and was moved to the starting rotation to begin the 2002 season.

Padilla was actually decent in his first two years as a starter for Philadelphia (2002-03), and went a combined 28-23 with a 3.45 ERA. He was chosen to his only career All-Star team in 2002.

However, injuries hit Padilla hard from 2004-05, and he was traded to the Texas Rangers following the 2005 season.

Neither Daal nor Lee ever amounted to much, and both have been out of baseball since 2006.

Figueroa never actually played in a game with the Phillies during his first stint with the team. Figueroa had stops in Milwaukee, Pittsburgh, Washington, and New York before finally appearing in 13 games with the Phillies in 2010.

Ironically enough, Figueroa was claimed off waivers by the Astros in July, and went 5-3 with a 3.22 ERA in 10 starts, easily the most productive stretch of his journeyman career.

22) San Francisco Giants Trade Joe Nathan, Franciso Liriano For A.J. Pierzynski

November 13, 2003

Full Details: Minnesota Twins trade C A.J. Pierzynski and cash to the San Franciso Giants for P Franciso Liriano, P Joe Nathan, and P Boof Bonser

After losing the World Series in seven games in 2002, and then losing in the LDS in 2003, the Giants thought that the addition of Pierzynski could potentially put them over the edge.

Statistically, Pierzynski was giving the Giants what they thought they were getting.

However, rumors of clashes with teammates surfaced quickly. Allegations of poor preparation, mishandling of the pitching staff, and just being a poor teammate in general surrounded A.J. One teammate went as far as to anonymously label him a “cancer.” Following the 2004 season, Pierzynski was released by the Giants.

Liriano, after struggling with injury and mechanical issues for nearly three years, returned to his ’06 form, and won the 2010 Comeback Player of the Year, going 14-10 with a 3.62 ERA and 1.26 WHIP, and striking out 201.

Despite missing the entire 2010 season with Tommy John surgery, Nathan has been one of the most consistent closers in baseball, and saved 246 games for the Twins from 2004-09.

The full boon of this trade has probably not yet been reached and, if the Twins could ever get a healthy Joe Nathan and Francisco Liriano together on the same roster, it would be a force to be reckoned with.

21) Marlins Trade Johan Santana To The Minnesota Twins For Jared Camp

Gregory Shamus/Getty Images

December 13, 1999

Full Details: Florida Marlins trade P Johan Santana with cash to the Minnesota Twins for P Jared Camp.

Santana was drafted in the Rule 5 minor league draft in 1999 from the Houston Astros by the Florida Marlins. They traded him that same day for Jared Camp.

Fast-forward nearly 11 years, and Santana has accumulated a career 133-69 record, 3.10 ERA, 1.12 WHIP, 1877 SO, two Cy Young awards (2004, 2006), and four All-Star appearances (2005-07, 2009). He's considered to be one of the best left-handed pitchers in baseball.

Jared Camp has yet to appear in a major-league camp. Enough said.

20) New York Mets Trade Tom Seaver to Cincinnati

June 15, 1977

Full Details: New York Mets trade P Tom Seaver to the Cincinnati Reds for INF Doug Flynn, P Pat Zachry, and OF Dan Norman

In what has become known as the "Midnight Massacre" to Mets fans, Tom Seaver was shipped from New York in the midst of the 1977 season. 

Contract negotiations between Seaver and Mets President Donald Grant were going poorly and had carried over into the season. Tension already existed when New York Daily News columnist Dick Young wrote an article citing Seaver's wife Nancy as the main reason behind Seaver's push for a new contract. The article put forth the idea that Nancy was jealous of Nolan Ryan and his wife, Ruth, because Nolan Ryan was making more money in California then Seaver was.

Exasperated, Seaver asked the New York front office for a trade, and the request was granted.

Seaver played nine more years of a Hall of Fame career, and was still effective. He appeared in two more All-Star games (1978, 1981), finished fourth in Cy Young voting and 21st in MVP voting in 1979, and second in Cy Young voting and tenth in MVP voting in 1981.

Flynn won a Gold Glove with the Mets in 1980, but was mainly a defensive specialist over four-and-a-half seasons with the Mets (1977-81). He was just a .238 career hitter.

Henderson finished just one point behind Andre Dawson for the 1977 Rookie of the Year, but never quite built on his early success. Henderson was traded to the Chicago Cubs after the 1980 season. His 1977 rookie campaign was the best year of his career.

Pat Zachry was decent at the onset of his Mets career. He was chosen as an All-Star after he was 10-4 during the first half. However, a broken foot suffered later that year ended his season. He finished 10-6 with a 3.33 ERA in 21 starts.

After that, Zachry could never really put a full season together. In 1981, he led the National League in losses (14), and home runs allowed (13). Following the 1982 season, Zachry was traded to the Dodgers. He would play in just three more seasons, used primarily as a reliever

Norman played parts of five seasons in the majors, four with the Mets. He was never a starter and never appeared in more than 69 games in one season.

The real ripple effects of this trade can certainly be seen. From 1977-1985, the Mets failed to make the playoffs once. They finished in last five times (1977-79, 1982-83), fifth two times (1980-81), and second two times (1984-85). It wasn’t until their World Series title in 1986 that the Mets regained the steam that they had had in the late 60s and early 70s.

19) Houston Astros Trade Joe Morgan To Cincinnati

November 29, 1971

Full Details: Houston Astros trade 2B Joe Morgan, OF Ed Armbrister, P Jack Billingham, OF Cesar Geronimo, and INF Denis Menke to Cincinnati Reds for INF Tommy Helms, 1B/OF Lee May, and INF Jimmy Stewart

In the 1970s, the “Big Red Machine” in Cincinnati garnered four NL pennants (1970, 1972, 1975-76) and two World Series wins (1975-76). This trade helped bring in some of the most important pieces to these teams.

Morgan went on to become one of the best second baseman of all-time. From 1975-76, both World Series years for the Reds, Morgan repeated as MVP and Gold Glove winner in the National League. In ’75, he hit 17 home runs, 94 RBI, and stole 67 bases, while posting a .327/.466/.508 batting line. In ’76, he hit 27 homers and 111 RBI (both career highs), while stealing 60 bases and batting .320/.444/.576. He was inducted into the baseball Hall of Fame in 1990.

Billingham went 87-63 with a combined 3.85 ERA over six seasons with the Reds (1972-77). He finished fourth in Cy Young voting in 1973 and sixth in 1974.

Geronimo, while never a wizard with the bat, was a staple in the Reds outfield from 1972-1980, and won four consecutive Gold Gloves from 1974-77.

Tommy Helms played decent baseball for the Astros from 1972-74. In 1975, at age 35, he was relegated to backup duty and appeared in just 64 games. He bounced around the majors for another two seasons before retiring.

Lee May played three years of solid baseball for the Astros. From 1972-74 he hit 81 home runs and 288 RBI. He was traded to the Baltimore Orioles in December of 1974, and hit 20-or-more home runs in each of the next four seasons.

Jimmy Stewart appeared in just 129 total games over two seasons (1972-73) with the Reds. He hit just .207.

18) New York Yankees Trade Fred McGriff To The Blue Jays

December 9, 1982

Full Details: New York Yankees trade 1B Fred McGriff, OF/1B Dave Collins, P Mike Morgan, and cash to the Toronto Blue Jays for 3B Tom Dodd and P Dale Murray

McGriff didn’t see significant major-league action until 1987, so, for a few years, it looked as if this would end up just another trade in the vast abyss of MLB transactions.

Not so.

McGriff went on to play 19 seasons of a borderline Hall of Fame career. He was first eligible in 2010, and received 21.5 percent of the vote. Other than Mark McGwire, McGriff has the most homers (493) of any currently eligible Hall of Fame candidate.

McGriff was a five-time All-Star (1992, 1994-96, 2000). He finished in the top 10 in MVP voting six times (1989-94). He was also a three-time Silver Slugger (1989, 1992-93), and led the league in homers twice (36 with the Blue Jays in 1989, and 35 with the Padres in 1992). He also won a World Series title with the Atlanta Braves in 1995.

Dodd has just 13 career MLB at-bats, all in 1986 with the Orioles. Murray appeared in 62 games out of the bullpen for the Yankees from 1983-85, before he was released on April 29 of the ’85 season.

17) Mets Trade Scott Kazmir For Victor Zambrano

Eliot J. Schechter/Getty Images

July 30, 2004

Full Details: New York Mets trade P Scott Kazmir and P Jose Diaz to the Tampa Bay Devil Rays for P Victor Zambrano and P Bartolome Fortunato

Despite Scott Kazmir’s recent decline, this trade still remains one of the biggest head-scratchers in the history of baseball.

As the Mets approached the trading deadline in 2004, they were just 49-53 (.480) and sat seven games out (fourth place) in the NL East.

However, for reasons still unknown to New York baseball fans, the Mets decided to become buyers, not sellers, at the trading deadline. Maybe it was the fact that the Mets had finished in the cellar of the NL West for the previous two years, and 49-53 was a drastic improvement over  anything the Mets had done.

Maybe GM Jim Duquette was clinically insane. Who knows.

In any case, the Mets famously traded then top-organizational pitching-prospect Scott Kazmir, along with minor-leaguer Jose Diaz, to the Tampa Bay Devil Rays for Victor Zambrano and Bartolome Fortunato.

Zambrano had a fairly extensive injury history and a fairly lackluster major-league resume. He was decent with the Mets in 2004 (who finished in fourth place and a full 25 games out of the division lead), and in 2005. However, Tommy John surgery effectively ended his major-league career, as he was fairly brutal in just nine starts from 2006-07. Zambrano played his last MLB game with the Baltimore Orioles in 2007.

Bartolome Fortunato played just two games in the majors after 2004. He hasn’t appeared in a big league game since 2006, and is no longer playing on any level of any major-league system.

On the other hand, Scott Kazmir went on to become one of the best young pitchers in the game. He currently ranks first in the history of the Tampa Bay organization in strikeouts (874), he is second in wins (55), games started (144), and innings pitched (834.0) and he is fourth in ERA (3.92).

16) Montreal Expos Trade Randy Johnson To The Seattle Mariners

May 25, 1989

Full Details: Montreal Expos trade P Randy Johnson, P Gene Harris, and P Brian Holman to the Seattle Mariners for P Mark Langston and a player to be named later (P Mike Campbell)

One of the more confusing transactions in the history of the sport, the trade of Randy Johnson to the Seattle Mariners by the Montreal Expos made little sense then and makes even littler sense now.

At least with some trades you can understand why they were made initially. Whether it’s sacrificing young talent in order to make a run at a championship, or just the fact that a prospect is seen as over the hill, some trades can be justified.

But not this one.

Mark Langston had five years of experience under his belt at the time of the trade. He had been a fairly decent, run-of-the-mill pitcher during his time in the majors, and he continued along the same trend for the rest of his career. He finished his career with respectable, albeit unspectacular, numbers: 179-158, a 3.97 ERA, a 1.35 WHIP, and 2,464 strikeouts over 16 seasons. He was even a four-time  All-Star (1987, 1991-93), a seven-time Gold Glove winner (1987-88, 1991-95.) He even has the fourth-most all-time career pick-offs (91).

Yet, when you get traded for Randy Johnson, there’s no real way to justify the trade.

At the end of May, the Expos were 27-25. They finished the season third overall in the National League West division. Randy Johnson was a 25-year-old talented pitcher who had struggled mightily with walks in parts of five seasons throughout the minors (7.04 BB/9 in 82 games from 1985-89). Despite his struggles, one must wonder why the Expos found it necessary to deal him, as they couldn’t have held out enormous hopes of making a deep playoff run.

Randy Johnson went on to have one of the best careers of any pitcher in MLB history. His 303 wins rank 22nd all time, and his 4,875 strikeouts are second to only Nolan Ryan (5714). His 10.61 K/9 is the highest mark of all-time.

And to top it off, Brian Holman, sent to Seattle along with Johnson, looked like a promising young pitcher until his career was ended by a series of shoulder injuries. He famously lost a perfect game with two outs in the ninth inning while pitching for Seattle on April 20, 1990.

Who knows: Maybe if the Expos were to keep Randy Johnson and Pedro Martinez (yikes) in Montreal, we wouldn’t even have the Washington Nationals. This just goes to show you how one trade can change the history of the sport forever.

15) Cardinals Trade Steve Carlton To Phillies For Rick Wise

February 25, 1972

Full Details: St. Louis Cardinals trade P Steve Carlton to the Philadelphia Phillies for P Rick Wise

Rick Wise played just two seasons for the Cardinals after the trade (1972-73), and was a combined 32-28 with a 3.24 ERA. He was traded after the '73 season to the Boston Red Sox.

Carlton, however, went 27-10 with a 1.97 ERA, 0.993 WHIP, and 310 strikeouts in his first year with the Phillies. He led the National League in wins, ERA, strikeouts, games started (41), complete games (30), and innings pitched (346.1), and captured his first career Cy Young award. 

He would play another 13-and-a-half seasons of a Hall of Fame career with the Phillies, which included another three Cy Young awards, and a World Series title for Philadelphia in 1980. His 329 career wins rank 11th all-time and his 4,136 strikeouts rank fourth all-time.

14) Houston Astros Trade Mike Cuellar To Orioles For Curt Blefary

December 4, 1968

Full Details: Houston Astros trade P Mike Cuellar, SS Enzo Hernandez, and Elijah Johnson to the Baltimore Orioles for OF/1B/C Curt Blefary and John Mason

John Mason never appeared in a major-league game and Curt Blefary played just one season for the Astros, hitting .253 in 155 games. He would bounce around baseball for the next two seasons.

Cuellar, on the other hand, had been a decent pitcher before the trade, but brought his game to a new level in Baltimore. He won the American League Cy Young award in 1969, his first year with the Orioles. He and Detroit Tigers pitcher Denny McLain both received the same number of votes and, therefore, tied for the award, the first-and-last time this has ever happened. All in all, he was 23-11 with a 2.38 ERA, 1.01 WHIP in 39 starts.

Over his eight-year career with the Orioles (1969-76), Cuellar would go a combined 120-77, with a 3.44 ERA and 1.19 WHIP. He would finish sixth-or-better in Cy Young voting three times (1969-70, 1974), and was an All-Star three times (1970-71, 1974). He also won 20-or-more games in three seasons (1969-70, 1974). During Cuellar’s eight seasons with the O’s, they would go to the World Series in three straight seasons (1969-71), and won it in 1970.

13) Phillies Trade Fergie Jenkins For Buhl and Jackson

April 21, 1966

Full Details: Philadelphia Phillies trade P Fergie Jenkins, OF/1B John Hernnstein, and OF Adolfo Phillips to the Chicago Cubs for P Bob Buhl and P Larry Jackson

When this deal was completed, Buhl was 37 years old and Jackson was 35. They had 24 years of major-league service between them. While they had both had pretty decent major-league careers (a combined 360 wins, five All-Star selections), neither would play past 1968.

Jenkins, however, was just 23 year olds with eight games of major-league service under his belt. He would go on to three All-Star appearances (1967, 1971-72) and one Cy Young award (1971). All in all, he finished 284-226, with a 3.34 ERA, 1.14 WHIP, and over 4,500 innings pitched. His 3,192 career strikeouts rank 12th all time. He spent eight of his 19 major-league seasons with the Cubs (1966-73).

Jenkins was inducted into the baseball Hall of Fame in 1991.

12) Tigers Trade John Smoltz For Doyle Alexander

August 12, 1987

Full Details: Detroit Tigers trade P John Smoltz to the Atlanta Braves for P Doyle Alexander

The Tigers got what they wanted in Doyle Alexander. A 36-year veteran at the time, Alexander went 9-0 with a 1.53 ERA and 1.21 WHIP throughout the remainder of the ’87 season. He helped lead the Tigers to a 98-64 finish (.605), and Detroit won the American League East by two games over the Toronto Blue Jays.

Alexander played two more seasons of baseball with the Tigers, and then retired. He finished his career with respectable numbers (194-174, 3.76 ERA) over 19 major-league seasons.

Unfortunately, the person traded for Alexander turned out to be John Smoltz.

Smoltz was only 20 years old at the time of the trade, and had just 38 games of minor-league experience under his belt.

Smoltz made his rookie debut with the Braves in 1988, and was an All-Star in 1989. After that, he slowly became one of the most dominant pitchers in the game.

Smoltz was one of the most established pitchers in the game when an arm injury caused him to miss all of the 2000 MLB season. As a result, Smoltz pulled a Dennis Eckersley, saving 154 games over the next four seasons (2001-2004). His 55 saves in 2002 remain tied for the third-highest single-season total of all-time.

All in all, Smoltz finished 213-155, with a career ERA of 3.33 and 3,084 total strikeouts. He is a surefire Hall of Famer.

11) Rangers Trade Sammy Sosa To White Sox For Harold Baines and Fred Manrique

July 29, 1989

Full Details: Texas Rangers trade OF Sammy Sosa, P Wilson Alvarez, and INF Scott Fletcher to the Chicago White Sox for DH/OF Harold Baines and 2B/SS Fred Manrique

The Rangers were looking for middle-of-the-lineup help when they traded for Harold Baines and Fred Manrique. Baines had been a solid hitter to that point in his career. Manrique, while not a wizard with the bat by any means, was a solid middle infielder.

However, in 153 games over the course of two seasons with the Rangers (1989-90), Baines hit .288 with just 16 home runs and 60 RBI. Both Baines and Manrique would be gone the following season.

Wilson Alvarez went on to pitch a no-hitter in his first game with the Chicago White Sox (Aug. 11, 1991). Alvarez went 15-8 during the 1993 season, and he was part of the triumvirate of himself, Jack McDowell, and Alex Fernandez, who went a combined 55-27 with a 3.16 ERA.

The White Sox won the American League West Division in 1993, finishing eight games over the second-place (you guessed it) Texas Rangers.

And every baseball fan knows what Sammy Sosa went on to do. Despite allegations of steroid use, Sosa went on to launch 609 career home runs (seventh all-time). He also led the league in home runs twice (50 in 2000 and 49 in 2002). He also finished with over 60 home runs in a season three times (66 in 1998, 64 in 2001 and 63 in 1999). Those totals rank third, fifth, and sixth respectively, all-time.

10) Mariners Trade Jason Varitek/Derek Lowe To Red Sox For Heathcliff Slocumb

July 1, 1997

Full Details: Seattle Mariners trade C Jason Varitek, P Derek Lowe to the Boston Red Sox for P Heathcliff Slocumb

In 1997, the Seattle Mariners dealt 23-year-old pitching-prospect Derek Lowe, and 25-year-old catching-prospect Jason Varitek to the Boston Red Sox in return for closer Heathcliff Slocumb.

The move was motivated by a desire to improve a below average bullpen, all in an attempt to fend off the California Angels and Texas Rangers in the West divison.

In 1996, Texas won the West while Seattle fell just short. The Mariners had been sixth worst in baseball for relievers runs per game (5.56), and had saved the third fewest games in the league (34).

Norm Charlton was their closer that season, and he had led the team with just 20 saves, while posting a 4.04 ERA and 1.40 WHIP. Charlton had been a run-of-the-mill drifter for most of his career, and he was 34 at the time.

Also in ’96, the Angels featured Troy Percival at the back end of their bullpen (36 saves), while the Rangers had Mike Henneman (31). Percival was far better than both Henneman and Charlton, and the Mariners figured that bringing in a closer with the good history of Slocumb would be well worth the prospects.

Well, they were wrong. Sort of.

For the remainder of 1997, Slocumb was a reliable option as the Mariners went on to capture the American League West title.

However, they lost 3-1 to the Baltimore Orioles in the American League Division Series. Slocumb was horrendous the rest of his career, lasting just another three seasons, and never saved more than three games in any season.

Ironically enough, Lowe turned into the reliable closer that the Mariners sought in the deal, as he saved 81 games for the Red Sox from 1999-2001.

In 2002, Lowe was converted into a starter. Over the next three years, Lowe went 52-27, with a combined 4.07 ERA and 1.32 WHIP. This includes a 21-win season in 2002. For a sinkerballer during the peak of the steroid era, that’s not too shabby.

And for a time, Jason Varitek was the best catcher in baseball. His blend of offense and game-calling ability made him a force to be reckoned with.

But, most importantly, the trade helped set up the Red Sox World Series championship in 2004, their first in 86 years, as both Lowe and Varitek were key members of the playoff run.

9) Expos Trade Cliff Lee, Brandon Phillips & Grady Sizemore For Bartolo Colon

David Maxwell/Getty Images

June 27, 2002

Full Details: Montreal Expos trade P Cliff Lee, 2B Brandon Phillips, OF Grady Sizemore, and 1B/OF Timmy Drew to the Cleveland Indians for P Bartolo Colon and P Tim Drew

When the Indians finalized this deal with the Expos, Colon was actually a pretty decent pitcher. He had finished fourth in Cy Young voting in 1999. Through his first 16 starts of 2002, Colon was 10-4 with a 2.55 ERA and 1.16 WHIP. Through 17 starts with the Expos, Colon was 10-4 with a 3.31 ERA and 1.32 WHIP. He finished sixth in Cy Young voting.

Ironically enough, because of his success in 2002, the Expos knew they wouldn’t be able to re-sign him after his current deal was up, and dealt him that offseason on Jan. 15, 2003 to the White Sox.

Grady Sizemore, when healthy, is one of the better outfielders in the game. He brings the rare combination of power and speed, and had at least 20-20 in every season from 2005-2008. He also has two Gold Glove awards (2007-08).

Phillips has turned himself into one of the better second baseman in the game during his time in Cincinnati. He’s very good defensively (Gold Gloves in 2008, 2010) and he is a decent hitter. While he strikes out a lot, he’s a decent base stealer, and has some pop in his bat (106 homers from 2006-2010).

And Cliff Lee has become of the best, if not the best, pitchers in the game. He’s being pursued by virtually everyone this offseason and will likely receive the largest contract of any free-agent pitcher in the history of the game.

His postseason record of 7-2, with a 2.23 ERA and anemic 0.816 WHIP makes him one of the best postseason pitchers of all-time. Through 76 playoff innings pitched, Lee has accumulated just eight walks.

The Expos essentially gave up three All-Stars and three of the best players in the game for half-a-season of service from Colon. Ouch.

8) Dodgers Trade Pedro Martinez To Montreal For Delino DeShields

November 19, 1993

Full Details: Los Angeles Dodgers trade P Pedro Martinez to Montreal Expos for INF Delino DeShields

When middle infielder Jody Reed left the Dodgers for the Milwaukee Brewers, they were left with a void at second base.

So, unfortunately, the Dodgers traded pitcher Pedro Martinez after the 1993 offseason to Montreal for infielder Delino DeShields.

Martinez went 11-5 in 23 starts for the Expos in 1994. He had a 3.42 ERA, and his 142 strikeouts were best on his team. Pedro helped lead the Expos to far and away the best record in baseball: 74-40 (.649), before the player strike ended the season.

DeShields would play just three seasons for the Dodgers (1994-96), and would hit just .241 in 370 combined games.

The Expos were on pace for 105 wins that season, and were heavily favored as World Series champs. However, no playoffs occurred that year, and the Expos slowly dissembled the team piece by piece after that, and they were never the same.

It’s a real travesty that there was no playoff baseball in 1994. Who knows how differently MLB history would look if there had been.

Pedro is now considered to be one of the best pitchers in the history of the game, and he is certainly a future Hall of Famer. His numbers become that much more impressive when you take into account the fact that he pitched at the height of the steroid era in baseball.

He's 13th all-time in career strikeouts (3,154) and first all-time in K/9 (10.61).

Fun fact of the day: Martinez' 2000 WHIP of 0.7373 is the lowest single-season mark in the history of baseball.

7) Red Sox Trade Jeff Bagwell For Larry Andersen

August 30: 1990

Full Details: Boston Red Sox trade 1B Jeff Bagwell for P Larry Andersen

"They passed out the press release near the dugout at five. I rolled it up, tossed it in the trash barrel in the runway, went up the stairs and walked home." - Peter Gammons

Boston sports writer and baseball guru Peter Gammons was highly critical of the Red Sox when they traded prospect Jeff Bagwell to the Houston Astros for reliever Larry Anderson. He believed that the Red Sox had just traded away a future batting champion.

While Bagwell never did lead the league in batting, I’d say his career numbers would qualify Gammons’ disparaging comments as semi-prophetic.

Bagwell won the Rookie of the Year in 1991. He went on to play 15 Hall of Fame-caliber seasons, all with the Houston Astros.

He was a four-time All-Star (1994, 1996, 1997, 1999), three-time Silver Slugger (1994, 1997, 1999), one-time Gold Glove award winner (1994), and one-time NL MVP (1994).

Bagwell is 34th all time in career home runs (440), 39th in extra base hits (969), 45th in RBI’s (1,529), and 21st in OPS (.948). He also holds a career batting average of .297 and 2,314 hits. Bagwell is at or near the top of nearly every offensive category in Houston Astros history. He’s considered one of the best Astros to ever play the game.

Andersen appeared in just 15 games for the Red Sox that year, before departing for San Diego via free agency in 1991. The Red Sox finished 88-74 in 1990, winning the American League East division, but were swept by the Oakland A’s in the League Championship Series.

The Sox essentially gave up a future Hall of Famer in Bagwell for 15 games of relief. Wow.

For the rest of the 90s, the Red Sox were mired in mediocrity and could never quite get over the hill. Maybe if they had held onto Bagwell, the “Curse of the Bambino” would’ve been significantly shortened.

6) Mets Trade Nolan Ryan For Jim Fregosi

December 10, 1971

Full Details: New York Mets trade P Nolan Ryan, P Don Rose, C Frank Estrada, and OF Leroy Stanton to the California Angels for SS Jim Fregosi

Before Nolan Ryan became the major league's all-time strikeout leader (5,714), he was a young, talented, and very wild pitcher for the New York Mets. Over his first five season with the Mets (1966, 1968-71), Ryan had a 6.4 BB/9 ratio, and was 29-38 overall.

However, in his first season with the Angels, Ryan made a noticeable jump. He set career bests (at the time) in wins (19), ERA (2.28), shutouts (9), innings pitched (284.0), games started (39), and strikeouts (329). He went on to pitch in an unheralded 27 MLB seasons, and he is one of the greatest pitchers of all-time.

Estrada and Rose both had insignificant major-league careers. Stanton was mostly run-of-the-mill except for his 1977 season, when he posted a 27 homer, 90 RBI, .275/.341/.511 line with the Mariners. He would play just one more season.

Fregosi, who had been a decent player over his career, was atrocious with the Mets. In 101 games in 1972, Fregosi had five home runs, 32 RBI, and hit .232/.311./.344. If you can believe it, his 1973 was worse, and Fregosi was dealt to the Texas Rangers in July. Fregosi never appeared in more than 78 games in a season after this, and was out of baseball following the 1978 season.

5) Lou Brock For Ernie Broglio

June 15: 1964

Full Details: Chicago Cubs trade OF Lou Brock, P Jack Spring, and P Paul Toth to the St. Louis Cardinals for P Ernie Broglio, OF Doug Clemens, and P Bobby Shantz

In two-and-a-half seasons with the Chicago Cubs, 24-year-old Lou Brock was just a .257 career hitter.

On the other hand, Ernie Broglio was seen as a top-tier starting pitcher. Through five-and-a-half seasons with St. Louis (1959-1964), Broglio was 70-55 with a 3.37 ERA, 1.26 WHIP, and 747 strikeouts. So when the Cubs dealt the struggling prospect to their division rival, it looked like the Cubs were getting a steal.

However, Broglio played just two-and-a-half more seasons in his career, posting ERAs well over six in each of his final two seasons. And, well, Lou Brock became one of the most electrifying players to ever live.

The Cardinals won the World Series in 1964, their first in 17 years; Brock hit .348 with 12 HR, 44 RBI, and 33 SB in 103 regular-season games to help get them there, and then he hit .300 with nine hits and five RBI in the World Series.

Brock’s single-season steal mark of 118 in 1974 is the second-highest total in the live-ball era to only Rickey Henderson (130 SBs in 1982.)

Brock went on to play another 15 seasons of a Hall of Fame career. His career total of 938 stolen bases is second all-time to, again, Rickey Henderson (1406).

Also, Brock is 44th all-time in runs scored (1610), and is a member of the illustrious 3,000 hit club (3,023 is 23rd all-tme). He was a six-time All-Star (1967, 1971-1972, 1974-1975, 1979), and a two-time World Series champion (1964, 1967).

Something tells me Cubs fans would like a do-over.

4) Reds Trade Frank Robinson For Milt Pappas

December 9, 1965.

Full Details: Cincinnati Reds trade OF/1B Frank Robinson to the Baltimore Orioles for P Milt Pappas, P Jack Baldschun, and OF Dick Simpson

Cincinnati Reds GM Bill DeWitt defended his trade of former Rookie of the Year, All-Star, and MVP Frank Robinson by labeling him as “an old 30” to the media.

Unfortunately for DeWitt, Robinson was anything but.

The following season, Robinson batted .316, with 49 homers and 122 RBI. He became the second-to-last winner of baseball’s triple crown.

He also happened to lead the Baltimore Orioles to their first World Series in team history, all while capturing MVPs of the ALCS and World Series.

Over his next six seasons, Robinson would lead the Orioles to four World Series appearances, including three straight from 1969-1971. The O’s were 2-2 in World Series play with Robinson.

Robinson was inducted into baseball's Hall of Fame in 1982.

Milt Pappas was mediocre over two-and-a-half seasons with the Reds. He went a combined 30-29 with a 4.04 ERA over this period.

Jack Baldschun and Dick Simpson both were minor contributors to the Reds. Neither lasted past the 1967 season.

3) Philadelphia Athletics Trade "Shoeless" Joe Jackson

July 25, 1910

Full Details: The Philadelphia Athletics trade OF "Shoeless" Joe Jackson and INF Morrie Rath to the Cleveland Naps for OF Bris Lord

When Joe Jackson was traded from the Philadelphia Athletics to the Cleveland Naps in 1910, he had played just a grand total of 10 games in the major leagues across two seasons (1908-1909).

The man he was traded for, outfielder Bris Lord, was just a career .232 hitter at the time of the trade. After the trade, Lord hit .280 throughout the remainder of 1910 and .310 in 1911. However, Lord’s production would fall significantly after 1911, and he would play just two more seasons in the major leagues.

But when you’re traded for “Shoeless” Joe Jackson, your level of talent is superfluous. There have been few players in the history of the game who have been as gifted

In 1911, in his first full season with Cleveland, Shoeless Joe hit an astonishing .408, the highest total among rookies all-time and the 13th highest mark all-time.

Jackson went on to have one of the most remarkable and controversial careers in the history of American sports. His .356 career batting average is the third highest total of all-time, and he’s generally regarded as one of the best pure hitters to ever play the game.

However, he was involved in the Black Sox scandal of 1919, when eight members of the Chicago White Sox team (Jackson included) were accused of throwing the World Series. Despite having 12 hits and a .375 batting average during the World Series, Jackson, along with his seven other teammates, were tried by a grand jury in 1920.

All eight members of the team were acquitted of any wrongdoings. However, Kenesaw Mountain Landis, the first commissioner of baseball, banned all eight from baseball for life, citing the need for baseball to clean up its image.

To this day, Jackson remains ineligible for the Hall of Fame, even though his numbers warrant a first-ballot admission.

2) Christy Mathewson For Amos Rusie

December 15, 1900

Full Details: Cincinnati Reds trade P Christy Mathewson to New York Giants for P Amos Rusie

The 29-year-old Rusie appeared in just three games for the Reds in 1901, going 0-1 with an 8.52 ERA before retiring. While he would end up in the Hall of Fame (inducted 1977), he never even won a game for the Reds.

Mathewson spent all but one game of his 16-year career in a Giants uniform, and what a career it was.

He finished with a 373-188 career record. His 373 wins are tied for third most all-time in MLB history. He has a career ERA of 2.13, sixth lowest all-time. He led the National League in wins four times (1905, 1907-98, 1910), ERA five times (1905, 1908-09, 1911, 1913) and finished with 20-or-more wins in 13 seasons, including 30 or more wins in four seasons (1903-05, 1908).

His 1908 line of 37-11 with a 1.43 ERA, 0.827 WHIP, 259 strikeouts, and over 390 innings pitched might have garnered him some Cy Young attention…if Cy Young wasn’t still playing.

Mathewson was inducted into the baseball Hall of Fame in 1936, joining four other players – George H. “Babe” Ruth, John “Honus” Wagner, Walter Johnson, and Ty Cobb – as the inaugural Hall of Fame class. He's considered one of the best pitchers of all-time.

1) Babe Ruth Sold To The New York Yankees For $100,000

January 3, 1920

In 1919, the Boston Red Sox finished 66-71 (.482). Despite defeating the Chicago Cubs in the World Series the year prior, the Red Sox were not able to compete for an American League pennant.

Also, in 1919, George “Babe” Herman Ruth led the league in home runs (29; 17 more than any other player), RBI (114), runs (103), OBP (.456), SLG (.657), and OPS (1.114).

To put this offensive domination into perspective, the league average for home runs for an entire team in 1919 was 28. Ruth had 29 single-handedly. This year, Josh Hamilton led the major leagues with an OPS of 1.044. Ruth’s was 0.070 points higher, more than 90 years before.

To top it off, Ruth was 9-5 in 15 games started with a 2.97 ERA. He even had one save. Talk about pure domination.

Because of the Red Sox struggles, team owner Harry Frazee felt the need to sell the team’s best player, Ruth, to ease his financial burdens. Frazee was heavily involved in the financing of a number of notable New York City theatrical productions. One of them, No No Nanette, is rumored to be the reason for the sale of Ruth, as Frazee needed the cash to finance the play (although this was later debunked as partial myth).

It seems more logical that Frazee sold Ruth purely on a contractual dispute. Ruth’s ballooning salary requests weren't convenient for a man with so many financial investment's.

Whatever the case, Ruth was sold for $100,000, which was, at the time, the highest price paid for a player in league history.

Virtually every baseball fan knows the ensuing history. The New York Yankees went on to win 26 World Series titles before Boston won another, 86 years after the trade. This comes despite the fact that they had won five titles from 1903-1918.

Ruth went on to become the most feared power hitter in the history of the game, revolutionizing the role of the offensive player. His 714 career home runs rank third all-time.

Around the late 80s and early 90s, the anachronistic phrase “the Curse of the Bambino” came into being. “The Curse” was applied to every single misfortune and postseason blunder that had plagued the Red Sox organization since their 1918 World Series title, until it was “broken” in 2004.