In baseball, one decision that could potentially set a team back years is a bad trade. I'm not talking about moves made at the July 31 deadline, but rather trades that teams make during the offseason so that they may acquire major league ready prospects or veterans who could start contributing immediately and stay on long-term.
While some of these trades have worked out, much like the New York Yankees dealing for Curtis Granderson after the 2009 season, some have also been epic failures. Mention the Mo Vaughn (pictured) trade to New York Mets fans, and they'll cringe while saying he ate all the money the team paid him.
That being said, seeing as how this is the offseason and some trades are rumored to be in the mix for some teams, let's go through history and look at every team's worst offseason trade of all time.
In 2007, Jose Valverde was a young fireballer who had paid his dues enough that he became the Diamondbacks' closer. That year, he led the majors with 47 saves as the team clinched the NL West and made it all the way to the NLCS, where they were swept by the Colorado Rockies.
Valverde easily could have helped the team continue its winning ways the following year, but his high value led team management to trade him to the Houston Astros. In return, the Diamondbacks received relievers Chad Qualls and Juan Gutierrez, along with infielder Chris Burke. The closer's role was taken over by the unpredictable Brandon Lyon, who registered 26 saves but with a 4.70 ERA.
Gutierrez spent 2008 in the minors and has been nothing but a liability out of the bullpen since returning to the majors in 2009, posting a 4.62 ERA and 1.41 WHIP. Burke appeared in 86 games and hit .194, his only redeeming factor being his defense.
The only good player that came out of the trade was Qualls, who had two productive seasons with Arizona before his game turned sour in 2010 and he was traded to the Tampa Bay Rays. Still, his setup work couldn't help the Diamondbacks in 2008 as the team finished 82-80 and out of the playoffs.
Valverde, on the other hand, had a great two years in Houston, saving 69 games before moving on to the Detroit Tigers as one of the more dominant closers in the game. The Diamondbacks ultimately did recover, but not from any of the players involved in this trade.
I understand that some teams have certain needs. Believe me, I do. Thus, when the Atlanta Braves traded for Dan Uggla this past offseason, I wasn't completely shocked.
Yet, at the same time, I didn't think it was a good trade. In it, the Florida Marlins acquired a solid left-handed pitcher in Mike Dunn and a talented hitter in infielder Omar Infante, who had finished third in the NL batting race with a .321 average.
The Braves received Uggla, a power-hitting second baseman with questionable defense and a penchant for striking out quite a bit.
His first season in a Braves uniform wasn't god awful, as he hit 36 home runs with 82 RBI and also had a 33-game hitting streak. Yet, Uggla struggled to find his groove all season long and finished 2011 with a career-worst .233 average while also making 15 errors in the field, tied for the most among second basemen. To add insult to injury, the Braves inked him to a five-year, $62 million contract.
In Florida, Infante hit .276 and Dunn posted a 3.43 ERA out of the bullpen. In a sense, the Braves got desperate for power and traded away two consistent producers for someone whose production is always a crapshoot.
Following the 2004 season, the Baltimore Orioles were once again looking to get over the hump and contend in the tough AL East. Shortly before the start of spring training in 2005, the team traded away popular utility man Jerry Hairston, Jr. and two minor-leaguers to the Chicago Cubs for outfielder Sammy Sosa, who had become a legend over the past several seasons thanks to his likeable personality and powerful bat that had given him three seasons with 60-plus home runs.
Sosa joined a lineup that already featured powerful hitters in first baseman Rafael Palmeiro and shortstop Miguel Tejada and for a good amount of time, the Orioles actually did pretty well in 2005. At one point, they were in first place for 62 consecutive days. Unfortunately, the team faltered in the second half of the season and finished 74-88 while Sosa never lived up to expectations and was limited to just 102 games due to injury.
In his lone season in Baltimore, Sosa hit .221 (his lowest batting average since 1991) with just 14 home runs and 45 RBI. Sure enough, no team offered him a major league contract for the 2006 season.
Meanwhile, in Chicago, Hairston hit .261 and played solid defense.
Red Sox fans know this trade all too well, as it resulted in a championship drought that lasted 86 years. Following the 1919 season, team owner Harry Frazee and power-hitting outfielder Babe Ruth were embroiled in a pay dispute that ultimately resulted in Ruth being traded to the rival New York Yankees.
This is where the trade gets interesting. In today's world, a hitter of Ruth's caliber would cost the team acquiring him some top prospects, cash and maybe one or two regulars from the major league roster. The man was simply that good.
Yet, when Frazee traded Ruth to the Yankees, here is what he got in return: $125,000 in cash, three $25,000 notes payable every year at six percent interest, and a $300,000 loan with Fenway Park's mortgage as collateral.
The rest, as they say, is history. Ruth went on to become one of the greatest home run hitters of all-time and the Yankees were one of the most successful teams of the 20th century. The Red Sox, on the other hand, did not win another World Series until 2004 thanks to what became known as "The Curse of the Bambino."
In the 1980s, the Chicago Cubs experienced a resurgence with the additions of second baseman Ryne Sandberg and relief pitcher Lee Smith, the latter of whom became one of the best closers in the game. Yet, as the team struggled in the latter half of the decade, the front office chose to clean house and go into rebuilding mode.
As a result, prior to the 1988 season, Smith was traded to the Boston Red Sox for mediocre starter Calvin Schiraldi (who had lost two games in the infamous 1986 World Series) and relief man Al Nipper. Almost instantly, the trade was a bust.
Schiraldi went 9-13 with a 4.38 ERA in his lone full season with the Cubs before being banished to the bullpen the following season and subsequently traded to the San Diego Padres. Nipper appeared in 22 games for the Cubs and posted a 3.04 ERA, but was out of baseball two years later due to injuries.
Smith, however, remained one of baseball's best closers for years. When he retired in 1997, he was the all-time leader in saves with 478.
In the early '90s, the Chicago White Sox needed a boost in the form of a powerful outfield bat. They had youngster Sammy Sosa on the team and he was showing flashes of potential, but not consistently enough to justify keeping him around.
Thus, before the 1992 season, Sosa and pitcher Ken Patterson were traded to the Cubs for veteran outfielder George Bell, who had hit .285 with 25 home runs and 86 RBI the season before.
Bell was productive in his first season on the South Side as he hit .255 with 25 home runs and 112 RBI, but his second season was far worse. He appeared in just 102 games and hit just .217 with 13 homers and 64 RBI.
On the North Side of Chicago, Sosa went on to become one of the most dominant home run hitters of his generation and helped bring the Cubs back to prominence for a short period of time, even winning the NL MVP Award in 1998.
Needless to say, I think it's obvious who got the better end of this trade.
For the first 10 years of his career, Frank Robinson was a stud outfielder for the Cincinnati Reds. Over that stretch, he hit .303 with 324 home runs and 1,009 RBI. These productive years earned Robinson the 1956 NL Rookie of the Year Award and the NL MVP Award in 1961.
Yet, calling the 30-year-old Robinson an "old 30", team owner Bill DeWitt sent his star outfielder to the Baltimore Orioles prior to the 1966 season in exchange for pitcher Milt Pappas and thus angered his team's fanbase. Given the outcome of the trade, I can't blame the fans.
Pappas went 30-29 in two-plus seasons with the Reds before being sent to the Atlanta Braves. In his first season in Baltimore, however, Robinson won the AL batting title with a .316 average and led the majors with 49 home runs while knocking in an AL-leading 122 RBI. The Orioles won the World Series that year and Robinson was named AL MVP.
Four years later, in 1970, Robinson and the Orioles won another World Series, this time against the very Cincinnati Reds that chose to trade the Hall of Famer.
In the entire history of the Cleveland Indians, one of the most popular players is easily outfielder Rocky Colavito. He debuted for the team in 1955 and became a full-time contributor the following year, instantly winning over the fans with his power hitting. From 1955-1959, he hit .272 with 129 home runs and won the AL home run crown in 1959 with 42.
Yet, just before the start of the 1960 season, controversial GM Frank "Trader" Lane sent Colavito to the Detroit Tigers for outfielder Harvey Kuenn, who had won the AL batting title the year before.
Kuenn ended up playing just one season for the Indians before Lane shipped him to the San Francisco Giants for aging pitcher Johnny Antonelli and outfielder Willie Kirkland.
Colavito ended up back in Cleveland in 1965, but it cost the Indians future All-Star pitcher Tommy John and 1966 AL Rookie of the Year Tommie Agee, both of whom were sent to the White Sox in exchange for the fan favorite.
When Darryl Kile signed with the Colorado Rockies before the 1998 season, the team thought it was getting a man who could be the ace of the staff. Instead, the thin air of Coors Field was not kind to Kile and he struggled mightily. In two seasons with the Rockies, he went 21-30 with a 5.84 ERA and 1.63 WHIP.
Thus, before the 2000 season, Kile and reliever Dave Veres were sent to the St. Louis Cardinals (along with prospect Luther Hackman) for pitchers Jose Jimenez, Manny Aybar and Rick Croushore. The change of scenery proved to be helpful to Kile as he won 20 games in his first season in St. Louis and finished fifth in NL Cy Young voting.
The trade didn't work out so well for the Rockies, however. Jimenez was inconsistent in four seasons with the team, Aybar appeared in one game before being sent to the Reds and Croushore was ineffective in six games before being sent to the Red Sox.
Long story short, the Cardinals got an ace while the Rockies were given the short stack.
December 5, 1963 is a date that Detroit Tigers fans will never forget. On that fateful day, team management dealt pitcher Jim Bunning to the Philadelphia Phillies for power-hitter Don Demeter and pitcher Jack Hamilton. At the time, Bunning was a consistent workhorse on a Tigers squad that, save for the 1962 season, had seen better days.
Unfortunately, this trade proved to be a bust for the Tigers. Demeter hit 22 home runs in his first year in a Tigers uniform, but was never the model of consistency that he was in Philadelphia. Hamilton was a non-factor over two seasons with the team, though he did garner recognition for beaning Tony Conigliaro in 1967.
Bunning, on the other hand, became a legend with the Phillies. Over four seasons, he went 74-46 with a 2.48 ERA and remarkable 1.03 WHIP. The highlight of his Phillies career was the perfect game he threw against the New York Mets in 1964, and I can only imagine how hard Detroit executives were kicking themselves.
During his first stint with the Houston Astros (nee Colt .45's) from 1963-1971, second baseman Joe Morgan gained a reputation as a player who was hit-or-miss when it came to batting average, but was great at getting on base and then advancing on a steal. Over that nine-year stretch, Morgan stole 195 bases.
Then, in November 1971, the Astros traded Morgan, infielder Denis Menke, pitcher Jack Billingham, outfielder Cesar Geronimo and prospect Ed Armbrister to the Cincinnati Reds. The Astros received first baseman Lee May and infielders Tommy Helms and Jimmy Stewart.
On paper, this wasn't a bad trade, but let's analyze the talent of the two main players involved, Morgan and May. As talented as May was, he was a typical power hitter. When he wasn't smacking home runs, he was striking out.
Morgan, on the other hand, became a star in Cincinnati. He won two straight NL MVP Awards in 1975 and 1976 and played in eight consecutive All-Star Games. In both of his MVP years, he also won two World Series rings.
May did his job as a power hitter in Houston, but Helms was average and Stewart a non-factor.
Now, in all fairness, the Royals ultimately reacquired David Cone via free agency before the 1993 season. Still, their initial trade of him before the 1987 season was just plain bad. The Kansas City native was sent to the New York Mets for catcher Ed Hearn.
While Cone went on to become one of the game's better pitchers, injuries limited Hearn to 13 games over two seasons with the Royals. Not even reacquiring Cone through free agency can shake the idiocy of this trade.
Before the 1997 season, the then-Anaheim Angels and Kansas City Royals made a trade that I'm still trying to figure out. The Angels sent powerful switch-hitter Chili Davis (pictured), who hit .292 with 28 home runs and 95 RBI the previous year, to Kansas City for pitcher Mark Gubicza. In 1996, Gubicza was 4-12 with a 5.13 ERA in 19 starts.
Davis went on to be productive in his lone season with the Royals, hitting 30 home runs with 90 RBI. The Angels were not so lucky with Gubicza, who made just two starts and went 0-1 with a 25.07 ERA and horribly unappealing 3.42 WHIP.
This trade probably had good intentions, as Angels management probably thought Gubicza was due for a rebound. But to trade one of your team's best hitters to get a rebound project? That just doesn't make sense.
When he became a full-time contributor for the Los Angeles Dodgers in 1993, Pedro Martinez was used as a strikeout-pitcher out of the bullpen. Yet, despite his talent, the team shipped him to the Montreal Expos before the 1994 season and got speedy infielder Delino DeShields in return.
DeShields would go on to steal 114 bases in three seasons in Dodger Blue, but only hit .241.
Martinez, on the other hand, was placed in the Expos' starting rotation and thus became one of the best strikeout pitchers of his generation. In 1997, he went 17-8 with a remarkable 1.90 ERA and won the first of his three Cy Young Awards. From 1997-2003, he led the majors in ERA five times and went a ridiculous 118-36.
Injuries would slow Martinez down in the latter years of his career, but he retired with a record of 219-100, 2.93 ERA and 3,154 strikeouts. Dodgers fans can only wonder what could have been had he remained with the team.
Until this offseason, the Marlins were notorious for penny-pinching and not retaining star players due to their high cost. The most notorious case of this occurred when team owner Jeffrey Loria sent the popular Miguel Cabrera and pitcher Dontrelle Willis to the Detroit Tigers for a collection of prospects highlighted by pitcher Andrew Miller and outfielder Cameron Maybin.
At the time of the deal, Cabrera was 24 years old and coming off of a four-season stretch during which he hit .318 with 126 home runs and 461 RBI, finishing fifth in MVP voting twice. He has continued his dominant stretch in four seasons with the Tigers, hitting .322 with 139 home runs and 461 RBI while Willis flamed out rather quickly and was a non-factor for Detroit.
Now, let's take a look at the two top prospects the Marlins received, Maybin and Miller. Maybin lasted three years in Florida and was never able to get consistent playing time, though he did finally show his potential with the San Diego Padres last season.
Miller lasted three seasons with the team and went 10-20 with a 5.89 ERA before being sent to the Boston Red Sox last season. Meanwhile, Cabrera was busy helping lead Detroit to an AL Central title and winning himself the AL batting crown.
As he did with most teams throughout most of his career, Gary Sheffield and his poor attitude wore out their welcome with the Milwaukee Brewers and was traded with Geoff Kellogg to the San Diego Padres just before the start of the 1992 season. The Brewers received pitcher Rickey Bones, infielder Jose Valentin and outfielder Matt Mieske.
Bones was mediocre, going 47-56 with a 4.71 ERA in five seasons with Milwaukee, while Valentin and Mieske became solid contributors despite the former's shoddy defense.
Sheffield, despite his attitude problem, went on to become one of the most threatening power bats of all time, finishing his 22-season career with 509 home runs and 1,676 RBI.
Being a small market team, it's hard for the Minnesota Twins to hang on to their young and talented players. Such was the case with then 28-year-old lefty ace Johan Santana, who was about to enter free agency following the upcoming 2008 campaign and would most definitely leave. Thus, team management chose to shop Santana and get top prospects in return.
The New York Mets ultimately were that team, sending the following to Minnesota for Santana: outfielder Carlos Gomez and pitchers Phil Humber, Kevin Mulvey and Deolis Guerra. In what can only be called a cruel turn of events, only one of these players, Guerra, is still part of the Twins organization.
Gomez showed promise as a speedster in Minnesota, but his impatience at the plate caused his batting average to suffer and he was traded to the Milwaukee Brewers for J.J. Hardy following the 2009 season. Humber appeared in 13 games for the Twins and posted a 6.10 ERA before being cut.
Santana went to New York and immediately signed a six-year deal worth $137.5 million. He has since become the quintessential great pitcher on a bad team. Don't let the recent injuries fool you, as this trade is quite possibly the worst in Twins history.
When then-Mets GM Steve Phillips chose to acquire first baseman Mo Vaughn prior to the 2002 season, the big lefty had just missed the 2001 season with an arm injury. Still, he had proven to be a valuable bat in the lineup for the Anaheim Angels. Thus, Phillips sent pitcher Kevin Appier to Anaheim and brought Vaughn to New York.
While Vaughn hit 26 home runs with 72 RBI in his first season as a Met, he hit just .259 as his weight was a constant issue. He appeared in just 27 games the following year before a bad knee closed the book on his baseball career. Ultimately, he appeared in just 166 games for the Mets.
Appier, on the other hand, fit in well in Anaheim. He went 14-12 with a 3.92 ERA and won a World Series ring in his only full season with the team.
Ask me to picture a powerful left-handed hitter from the 1990s, and I'll picture Fred McGriff. The man's swing was just so perfect and he was such a great teammate. Upon retiring in 2004, he had 493 career home runs.
That being said, I'm simply shocked and wondering what possessed my beloved New York Yankees, in December 1982, to trade McGriff, pitcher Mike Morgan and outfielder/first baseman Dave Collins to the Toronto Blue Jays for reliever Dale Murray and outfielder Tom Dodd. We all know McGriff's story, but take a look at what the Yankees got in the deal.
Dodd never appeared in a game for the Yankes and Murray was largely ineffective. In two-plus seasons with the team, he posted a 4.83 ERA and 1.46 WHIP.
He may be best known for his time in pinstripes, but Roger Maris was actually a talented young outfielder for the Cleveland Indians and then-Kansas City Athletics before heading to New York. He was sent to the Yankees in December 1959 along with infielders Joe DeMaestri and Kent Hadley. The Athletics received first baseman Marv Throneberry, outfielder/first baseman Norm Siebern, outfielder Hank Bauer and pitcher Don Larsen.
Throneberry was fairly average in Kansas City and was out of baseball just a few years later, while the aging Bauer was a shell of his former self and Larsen was just plain awful. The only man who was effective was Siebern, who hit .308 with 25 home runs and 117 RBI for Kansas City in 1962.
In New York, Maris won two consecutive MVP awards and in 1961...well, we all know that story.
Believe it or not, the man in that picture is Hall of Famer Ryne Sandberg. Yes, he actually appeared in 13 games for the Philadelphia Phillies in 1981 before being traded to the Chicago Cubs that offseason. The story of the trade itself is interesting.
After the 1981 season, Phillies' management had grown fed up with shortstop Larry Bowa and his attitude and were looking to trade him. In the end, they traded him and Sandberg to the Cubs for infielder Ivan de Jesus.
Ultimately, this is easily the worst trade the Phillies ever made. Sandberg went on to have a Hall of Fame career as one of the best second basemen in baseball history, and de Jesus hit .249 in three seasons in Philly.
In an 18-year career, second baseman Willie Randolph earned a reputation as a scrappy hitter whose patience at the plate always paid off in the end, as he could beat the opposition with a walk and a stolen base just as easily as he could with a base hit. He made his major league debut for the Pittsburgh Pirates in 1975, just 20 years old.
That offseason, the Pirates sent Randolph and pitchers Ken Brett and Dock Ellis to the Yankees for pitcher Doc Medich. When the dust settled, Randolph went on to become one of the most popular players in Yankees history while Medich lasted just one season in Pittsburgh before being sent to the Oakland Athletics the following year.
For the first four seasons of his career, Ozzie Smith was a speedy and slick-fielding shortstop for the San Diego Padres. Unfortunately, he and the team could not agree on a fair contract and thus, before the 1982 season, Smith was traded to the St. Louis Cardinals.
To complete the trade, the Cardinals sent over shortstop Garry Templeton, who was a fine player but had punched his ticket out of St. Louis after making an obscene gesture at heckling fans.
The rest is all history. Smith went on to become one of the best defensive shortstops in baseball and won a World Series his first year in St. Louis, ultimately making the Hall of Fame in 2002.
Templeton spent eight-plus years with the Padres and was just average, hitting around .250 most of the time. And all because Padres management didn't want to give Smith his money!
Going into the 2004 season, the San Francisco Giants needed a catcher to replace Benito Santiago. During the offseason, they pulled off a trade for which some Giants fans still haven't forgiven GM Brian Sabean.
You see, Sabean sent pitchers Joe Nathan, Francisco Liriano and Boof Bonser to the Minnesota Twins in exchange for catcher A.J. Pierzynski, who had hit .312 with 11 home runs and 74 RBI in 2003. He would hit .272 with 11 home runs and 77 RBI in one season with the Giants before leaving for the Chicago White Sox via free agency.
Nathan, on the other hand, would go on to become one of baseball's elite closers once on the Twins and Liriano has shown flashes of potential here and there. The sad part is that Sabean gave up on both of them just for a catcher who stuck around for a year.
In 2006, Rafael Soriano had a great season coming out of the bullpen for the Mariners. In 53 games, the hard-throwing righty posted a 2.25 ERA.
Yet, with the Mariners needing help in the starting rotation, Soriano was traded to the Atlanta Braves that offseason for lefty Horacio Ramirez. In just one season, Mariners fans were missing Soriano.
To be absolutely blunt, Ramirez was a complete and utter joke for Seattle. In his one season with the team, he went 8-7 with a horrible 7.16 ERA and even worse 1.84 WHIP.
Meanwhile, Soriano has gone on to become a successful closer/setup man. Ramirez appeared in 12 games for the Angels in 2011 after missing all of 2010.
For the first seven years of his career, Steve Carlton was a talented young left-hander for the St. Louis Cardinals. With his hard fastball and biting slider, he developed a reputation as a decent strikeout pitcher and a force to be reckoned with on the mound. In 1967, he won his first World Series ring with the team.
Yet, due to a contract dispute prior to the 1972 season, Cardinals owner Gussie Busch traded Carlton to the Philadelphia Phillies for Rick Wise. On paper, it's not a bad trade seeing as how Wise went 32-38 with a 3.24 ERA in two years in St. Louis.
However, Carlton went on to become a legend in Philadelphia as in 1980, he helped lead the team to its first NL Pennant in 30 years. Soon after, he went 2-0 with a 2.40 ERA as the Phillies took home their first World Series championship.
Still not convinced? Look at it this way. Rick Wise had a stint with the Cardinals. With the Philadelphia Phillies, Carlton had a history.
For the first two years of his career, Bobby Abreu was a talented outfield prospect in the Houston Astros organization, his greatest strengths being his bat and his strong throwing arm in right field. For some reason, the Astros didn't see much use for him and left him unprotected in the 1997 Expansion Draft. There, he was taken by the Tampa Bay Devil Rays.
Hours later, Abreu was traded to the Philadelphia Phillies for shortstop Kevin Stocker in a move that team ownership probably regrets to this day. Abreu went on to become a star in Philadelphia, New York and Los Angeles while Stocker went on to hit .208 his first year in Tampa Bay. He would hit .299 the next year, but was not a starter.
Stocker was out of the majors by 2000, while Abreu is still active today.
If there's one type of trade that burns me up, it's when teams trade top prospects for veterans just so they can win sooner rather than later. Whatever happened to patience being a virtue? Anyway, a perfect example of this occurred in December 2005, when the Texas Rangers acquired pitchers Adam Eaton and Akinori Otsuka from the San Diego Padres.
The Rangers ended up sending three players to the Padres: pitcher Chris Young, outfielder Terrmel Sledge and a young first baseman named Adrian Gonzalez.
In the end, the Rangers got the short end of the stick. Eaton only made 13 starts for the team, going 7-4 with a 5.12 ERA while Otsuka saved 32 games in 2006.
In San Diego, Young was solid despite recurring shoulder problems while Gonzalez went on to become one of the best hitting and fielding first baseman in all of baseball. Today, he is the starting first baseman for the Boston Red Sox.
For almost 10 years, Roy Halladay was a force to be reckoned with in the Toronto Blue Jays starting rotation. He won the AL Cy Young Award in 2003 and regularly contended for it during his time in Toronto. From 2002-2009, his prime rotation years with the team, Halladay went 130-59 with a 3.13 ERA and 1.13 WHIP.
Yet, being a small market team, the Blue Jays knew that the odds of signing Halladay once he hit free agency were slim to none. Thus, before the 2010 season, they traded him to the Philadelphia Phillies in a three-team deal that also sent Cliff Lee to the Seattle Mariners.
The Blue Jays received catcher Travis D'Arnaud, outfielder Michael Taylor and, the centerpiece of the trade, top pitching prospect Kyle Drabek.
Taylor was immediately traded to Oakland for Brett Wallace and D'Arnaud is doing fine in the minors, but Drabek has thus been a royal flop for Toronto. I know it's a bit early to judge him, but the whole point of acquiring him was because he was a major league ready prospect, or so people thought.
In 21 games for the 'Jays, the 24-year-old Drabek has gone 4-8 with a 5.83 ERA while Halladay has taken Philadelphia by storm, winning the 2010 NL Cy Young Award and pitching a no-hitter in the 2010 NLDS.
I may be cheating a bit here, seeing as how this bad offseason trade occurred when the Washington Nationals were still called the Montreal Expos, but it's just that horrible that it has to be discussed. Following Pedro Martinez's Cy Young-winning 1997 season, instead of negotiating a contract with him so that he could be the franchise's saving grace, the Expos traded Martinez to the Boston Red Sox for pitching prospects Carl Pavano and Tony Armas, Jr.
Now, let's talk a bit about what makes a good trade. As I mentioned with the Babe Ruth trade, if you're a GM or owner and have a top-tier player you need to unload, you talk to teams and see which ones are willing to give the best package for said player. In Martinez's case following the 1997 season, he should have easily garnered some top prospects and maybe a regular from a major league roster.
Looking at the minor league stats of both Pavano and Armas, only Pavano could be called a top prospect, and even that's stretching it. Neither had a memorable tenure with the team as Pavano went 24-35 with a 5.67 ERA in four and a half seasons before being traded to the Marlins, while Armas went 48-60 with a 4.45 ERA. Pavano has managed to become an average pitcher in his career, currently pitching for the Minnesota Twins, but Armas last played in the majors for the Mets in 2008.
Simply put, the fact that the Expos/Nationals got so little for a pitcher as talented as Martinez is ridiculous. Had GM Jim Beattie acted like the decision-maker for a legit franchise rather than one just trying to get by, perhaps the team would have gotten more in return.