MLB Trades: The 15 Biggest Rip-Offs in Baseball History

As the trade deadline approaches later this week, teams will be forced to make the tough decision whether to mortgage the future and deal some of their top young talent for a chance to add a key veteran and win now.

Some times this pays off, sometimes it doesn't, and sometimes it is a catastrophic decision that the organization looks back on frequently as a dark day in team history.

So here is a look at the 15 biggest rip-offs in baseball history. Some are deadline deals involving prospects, some are off-season moves by a team looking to upgrade a position, and some are mid-season veteran-for-veteran swaps. One thing they all have in common is that one team clearly came out on top of these deals.

Twins Acquire Joe Nathan, Francisco Liriano, Boof Bonser from the Giants

Date: November 14, 2003

Twins Got: Joe Nathan, Francisco Liriano, Boof Bonser

Giants Got: A.J. Pierzynski and cash

With a World Series appearance in 2002 and another trip to the playoffs in 2003, the Giants were a team on the cusp of something special, and they thought they may have found their missing piece in the off-season leading up to the 2004 campaign in Twins catcher A.J. Pierzynski.

Coming off of a .312 BA, 11 HR, 74 RBI season, the 26-year-old catcher should have been untouchable, but with Joe Mauer on the way he became expendable, and the Giants offered up a trio of pitchers that the Twins simply could not refuse.

Pierzynski did his part on the field in 2004, hitting .272 with 11 HR and 77 RBI. However, he clashed with teammates and coaches in the clubhouse, and despite all they gave up to get him, the Giants released him after just one season with the team.

For the Twins, Nathan saved 246 games in six seasons before suffering an injury in spring training of 2009 that he is still trying to fully bounce back from. Liriano took the baseball world by storm with a 12-3 rookie season in which he made the All-Star team, and after missing time with Tommy John surgery he enjoyed a bounce-back season last year. Bonser went 18-25 in three seasons with the Twins before moving on. All in all, a steep price for a player who was released the following season.

Chicago Cubs Acquire Aramis Ramirez and Kenny Lofton from the Pittsburgh Pirates

Date: July 23, 2003

Cubs Got: Aramis Ramirez, Kenny Lofton, and Cash

Pirates Got: Bobby Hill, Jose Hernandez, and Matt Bruback

With the Cubs in contention at just 5.5 games out of first place on July 23, the Cubs made a move to upgrade two of their biggest holes by acquiring a lead-off hitter and center fielder in Kenny Lofton, and a middle-of-the-order slugger and third baseman in Aramis Ramirez.

Ramirez was immediately plugged into the fifth spot in the lineup and he hit .259 with 15 HR and 39 RBI the rest of the season. Lofton was even better, hitting .327 with 3 HR, 20 RBI and 12 SB as he made yet another stop on his 17-season, 12-team career.

Lofton was gone by the next season, but served a crucial role in the playoffs, going 16-for-52. Ramirez is in his ninth season with the Cubs and has hit .293 with 231 HR and 773 RBI as one of the best third basemen in Cubs history.

Hill played through the 2005 season with the Pirates but never grew into an everyday player. Hernandez hit .223 with 3 HR and 21 RBI the rest of the 2003 season and was not re-signed at season's end. Bruback never appeared at the major league level. All in all, a terrifically lopsided deal for the Cubs.

Indians Acquire Cliff Lee, Brandon Phillips, Grady Sizemore from the Expos

Date: June 27, 2002

Indians Got: Cliff Lee, Grady Sizemore, Brandon Phillips, Lee Stevens

Expos Got: Bartolo Colon, Tim Drew

Coming off of a 68-94 season in 2001, the Expos surprisingly found themselves in contention on June 27 of the following season, just 6.5 games out of first place.

With just two everyday players under the age of 27, and a young pitching staff, the Expos decided to go for it and traded the farm to land the frontline starter they were lacking in Bartolo Colon, and he delivered going 10-4 with a 3.31 ERA in 17 starts with the Expos. However, the team fell short and finished a whopping 12.5 games out of the wild card, and it cost them dearly.

Sizemore would turn into one of the game's top power-speed threats for the Indians before running into injuries, Lee would win the AL Cy Young in 2008 and net the Indians a bevy of prospects in a later deal, and Phillips has grown into one of the game's top second basemen with the Cincinnati Reds.

So while the deal did not necessarily benefit the Indians in the long-run, it hurt the Expos/Nationals greatly, as they have not finished higher than fourth in the NL East since that season, and could certainly use those players now or the prospects they could have gotten for them in a deal.

Minnesota Twins Acquire Johan Santana from the Florida Marlins

Date: December 13, 1999

Twins Got: Johan Santana and cash

Marlins Got: Jared Camp

Often times, teams will select a player in the Rule 5 draft knowing another team has their eye on them, and then flip them to that team for a prospect or cash. That is exactly what happened in 1999, when the Marlins selected 20-year-old left-hander Johan Santana from the Astros organization, then sent him to the Twins hours later with some cash for Jared Camp.

A former fifth-round selection back in 1995, Camp was a mid-level prospect at best. He had enjoyed success in 1999 after moving from the rotation to the bullpen, posting a 2.81 ERA and saving 12 games between three different levels.

Santana made 30 appearances while filling his obligatory spot on the Twins roster, tallying an unimpressive 6.49 ERA over 86 innings and making five starts. He would make just 15 appearances the following season, but by 2002 he started to put it together, and between 2002 and 2003 he went 20-9 with a 3.04 ERA as a swingman, starting 32 games and relieving 40.

In 2003, he joined the rotation full-time, and the results were staggering as he went 20-6 with a 2.61 ERA, 265 Ks and won the first of two AL Cy Young Awards. In total, Santana would go 93-44 with a 3.22 ERA in eight seasons with the Twins, while Camp never made it to the majors and was out of baseball by 2003.

Boston Red Sox Acquire Derek Lowe, Jason Varitek from the Seattle Mariners

Date: July 31, 1997

Red Sox Got: Jason Varitek, Derek Lowe

Mariners Got: Heathcliff Slocumb

With the Mariners clinging to a half-game lead in the AL West at the deadline, closer was a clear area of concern as incumbent stopper Norm Charlton had struggled to the tune of a 7.27 ERA with just 14 saves to his credit.

The team found a suitable replacement in Red Sox veteran Heathcliff Slocumb, as he saved 10 games and registered a 4.13 ERA while striking out a batter an inning after coming over in a last-minute trade.

However, it cost the Mariners dearly.

Derek Lowe, coincidentally, would turn into the closer that the Mariners needed, saving 85 games in his first four seasons in Boston before joining the rotation and winning 52 games in three seasons, including 21 in his first year as a starter.

Jason Varitek would grow into one of the best catchers in baseball and the team captain, as his offensive prowess and ability to handle a pitching staff made him invaluable. Both players were key to the Red Sox' 2004 World Series run, while Slocumb would struggle over the next three seasons before retiring.

Montreal Expos Acquire Pedro Martinez from the Los Angeles Dodgers

Date: November 19, 1993

Expos Got: Pedro Martinez

Dodgers Got: Delino DeShields

With the departure of Jody Reed, the Dodger found themselves in need of a starting second baseman heading into the 1994 season, and they landed a dynamic speed threat in the Expos' Delino DeShields.

Still just 24 years old, DeShields had stolen 187 bases in four seasons in the league, while posting a respectable .277 average with 6 HR and 45 RBI. However, he struggled to a .250 average and stole just 27 bases in his first year with the Dodgers and spent just three seasons with the team.

In return, the Expos got 22-year-old Pedro Martinez, who was arguably the best middle reliever in baseball the previous season when he went 10-5 with a 2.61 ERA and 119 Ks in 107 innings. However, he was wild and it was unclear whether he would be a starter down the road.

That was quickly cleared up, however, when the Expos plugged him into the rotation to open the 1994 season and he went 11-5 with a 3.42 ERA. He would only get better, culminating in an NL Cy Young Award in his final season with the team in 1997 when he went 17-8 with a 1.90 ERA, 305 Ks and a whopping 13 complete games.

Houston Astros Acquire Jeff Bagwell from the Boston Red Sox

Date: August 30, 1990

Astros Got: Jeff Bagwell

Red Sox Got: Larry Andersen

With a 6.5 game lead in the division on August 30, the Red Sox seemed to be on their way to the playoffs, and the team decided adding another arm to the back-end of the bullpen would be key if they hoped to be legitimate contenders.

The settled on adding 37-year-old Larry Andersen from the Astros. He was in the midst of a fantastic season, as he had posted a 1.95 ERA in 73.2 innings of relief work for the Astros, and he was equally impressive after the trade with a 1.23 ERA in 22 innings. The Red Sox went on to win the AL East, but were swept by the Athletics in the ALCS. Andersen then left in free agency that off-season.

Bagwell, the Red Sox' fourth round selection in the 1989 draft, had a line of .333 BA, 4 HR and 61 RBI at Double-A in what was his first full professional season prior to the trade. He would go on to win the NL Rookie of the Year the following season with a .294 BA, 15 HR, 82 RBI line.

It didn't stop there, however, as he went down as one of the greatest players in Astros history, with a career line of .297 BA, 449 HR and 1,529 RBI. Add in four All-Star appearances, three Silver Sluggers, and the 1994 NL MVP and he makes a strong case for Hall of Fame enshrinement.

Chicago Cubs Acquire Ryne Sandberg from the Philadelphia Phillies

Date: January 27, 1982

Cubs Got: Ryne Sandberg, Larry Bowa

Phillies Got: Ivan DeJesus

After spending 12 seasons with the Phillies, shortstop Larry Bowa was looking for an extension that would allow him to finish out his career with the team, but at 35 years old and with declining numbers, the Phillies had other ideas.

They found a taker for the veteran in the Cubs, who offered up 27-year-old Ivan DeJesus in return. Originally a Dodgers farm hand, DeJesus had shown promise since joining the Cubs in the trade that also brought Bill Buckner to the Cubs. Over his first four seasons with the team, he had averaged a line of .272 BA, 4 HR, 40 RBI and 33 SB. However, he had a disastrous 1981 season, hitting just .194 over 403 at-bats.

Because DeJesus still had some upside, the Cubs also landed a third base prospect in the deal in the form of 22-year-old Ryne Sandberg.

The Cubs immediately plugged Sandberg into the starting lineup, moved him to second base, and two seasons later he was the NL MVP after leading the Cubs to the playoffs. He would finish his career as one of the best second basemen to ever play the game with an offensive line of .285 BA, 282 HR and 1,061 RBI to go along with nine Gold Gloves.

Philadelphia Phillies Acquire Steve Carlton from the St. Louis Cardinals

Date: February 25, 1972

Phillies Got: Steve Carlton

Cardinals Got: Rick Wise

There is no question that Steve Carlton was a good pitcher from the start of his career, as he posted a 57-53 record in his first six seasons in the league with a terrific 2.98 ERA. However, when he followed up a 1970 season in which he led the NL with 19 losses by going 20-9 in 1971, the Cardinals decided to deal the then 26-year-old when his value seemed to have peaked.

In return, the got another 26-year-old in Wise who was coming off of a 17-win season and had won 45 games in the past three seasons. He would go on to win 16 games in each of his two seasons with the Cardinals before they flipped him to the Red Sox for Reggie Smith and Ken Tatum.

Carlton, on the other hand, would go on to be one of the best pitchers of the 1970s, starting things out with a 27-10 record, 1.97 ERA and 310 Ks in his first year in Philadelphia, winning the pitching Triple Crown and the first of four NL Cy Young Awards.

With 329 career wins and 4,136 strikeouts, Carlton is a Phillies icon and one of the best left handers to ever toe the rubber.

Baltimore Orioles Acquire Frank Robinson from the Cincinnati Reds

Date: December 9, 1965

Orioles Got: Frank Robinson

Reds Got: Milt Pappas, Jack Baldschun and Dick Simpson

Looking to bolster the team's pitching rotation, Reds GM Bill DeWitt made the controversial decision to deal superstar Frank Robinson to the Orioles for Milt Pappas, stating that Robinson was "an old 30" to try to justify the move.

It didn't take long for DeWitt to eat his words, as Robinson won the AL Triple Crown in his first season with the Orioles, hitting .316 with 49 HR and 122 RBI, leading the team to a World Series title in the process.

He would play a total of six seasons with the Orioles, hitting .300 with 179 HR and 545 RBI, showing that he was far from washed up at the age of 30, and cementing his place as one of the best hitters to ever play the game.

Pappas went 12-11 with a 4.29 ERA in his first season with the Reds, and 30-29 with a 4.04 ERA overall in parts of three seasons with the team before he was traded to the Braves. Neither Baldschun nor Simpson did much of anything for the Reds, and were out of Cincinnati by the end of the 1967 season.

St. Louis Cardinals Acquire Lou Brock from the Chicago Cubs

Date: June 15, 1964

Cardinals Got: Lou Brock, Jack Spring, Paul Toth

Cubs Got: Ernie Broglio, Doug Clemens, Bobby Shantz

Heading into the 1964 season, the Cubs had seen flashes of brilliance from then 25-year-old Lou Brock as he averaged a line of .260 BA, 9 HR, 36 RBI and 20 SB. However, with the team in need of pitching—and Brock hitting just .251—the Cubs decided to deal him for a package centered around Ernie Broglio.

Something seemed to immediately click for Brock after the trade, as went on to hit .348 with 12 HR, 44 RBI and 33 SB in 103 games after the trade. He would go on to play 16 seasons for the Cardinals, racking up over 3,000 hits and swiping 938 bases on his way to the Hall of Fame.

Broglio, who was coming off an 18-win season and also had a 21-win season to his credit, was an epic flop as seemingly everyone except the Cubs knew he had nothing left in his arm. He would go 4-7 with a 4.04 ERA after the trade and a total of 7-19 with a 5.40 ERA before retiring after the 1966 season.

None of the other four players involved would do anything of note, and "Brock for Broglio" is still the benchmark for foolish mid-season trades.

Chicago White Sox Acquire Billy Pierce from the Detroit Tigers

Date: November 10, 1948

White Sox Got: Billy Pierce, $10,000

Tigers Got: Aaron Robinson

With the Tigers looking for a starting catcher heading into the 1949 season, they found a trade partner in the Chicago White Sox. Coming off of a 101-loss season, the White Sox had a lot of work to do, and had little use in the long-term for a 33-year-old former All-Star catcher.

So they sent Robinson to the Tigers, where he put up solid numbers in 1949 with a line of .269 BA, 13 HR and 56 RBI. However, he was out of the league two seasons later after falling off significantly after the 1949 campaign.

In return for Robinson, the White Sox got a 21-year-old left-hander named Billy Pierce who had just 27 big league appearances and five starts under his belt. He would immediately join the White Sox rotation, going on to win 186 games with a 3.19 ERA in 13 seasons on the South Side.

The fact that the Tigers threw $10,000 into the deal for the White Sox is salt in the wound, as they gave up one of the best pitchers of the 1950s, and paid someone to take him off their hands.

Babe Ruth Is Sold to the New York Yankees

Date: January 3, 1920

Yankees Got: Babe Ruth

Red Sox Got: $100,000

It was the off-season following the 1919 baseball season, and the Red Sox had a full-blown superstar on their hands in Babe Ruth. Formerly a pitcher who could really hit, Ruth was now an outfielder who occasionally pitched, and he was putting up numbers that no one had ever seen before.

With a batting line of .322 BA, 29 HR and 114 RBI, and a pitching record of 9-5 with a 2.97 ERA over 133.1 innings, it was a season for the ages. Whether it was Ruth asking for his salary to be doubled to $20,000, or whether the stories that Red Sox owner Harry Frazee was trying to finance a theatrical production were in fact true, for one reason or another Ruth was put on the trade block.

The White Sox offered up $60,000 and "Shoeless" Joe Jackson for Ruth, but Frazee declined and instead took the Yankees' deal and the full $100,000 that he was seeking.

Thus, the Curse of the Bambino was born, as the Red Sox would go without a World Series until the curse was broken in 2004. Meanwhile, the Yankees became baseball's most revered franchise and piled up titles with Ruth leading the way.

Cleveland Naps Acquire "Shoeless" Joe Jackson from the Philadelphia Athletics

Date: July 30, 1910

Naps Got: "Shoeless" Joe Jackson and Morrie Rath

Athletics Got: Bris Lord

The actual trade occurred on July 23, 1910 with the Naps receiving Rath and a player to be named for Lord.

Rath was a 23-year-old second baseman hitting just .154 at the time of the trade. He hit just .194 following the trade, and he appeared in a grand total of 24 games for the Naps before being selected by the White Sox in the 1911 Rule 5 Draft. He played a total of six seasons, with a career line of .254 BA, 4 HR and 92 RBI.

Lord, a 26-year-old outfielder, was hitting just .219 at the time of the deal, but he picked things up after joining the Athletics and hit .280 with 1 HR and 20 RBI in 70 games after the trade. He followed that up with his best pro season, when he hit .310 with 3 HR and 55 RBI as an everyday player. However, he would be out of baseball after the 1913 season.

That brings us to Jackson, who was seemingly just a throw-in in this deal. The 22-year-old had hit .150 over 40 at-bats the previous two seasons and was in the minors at the time of the deal. He quickly showed he was something special though, hitting .387 with1 HR and 11 RBI in 20 games after the break.

By the following season, it was clear the Naps had come away with a steal as Jackson hit .408 with 7 HR and 83 RBI in his first full season. He spent six seasons with the Naps before being traded to the White Sox, and while his career is a controversial one with the Black Sox scandal leading to his ban from baseball, his numbers certainly show he was a Hall of Fame player.

New York Giants Acquire Christy Mathewson from the Cincinnati Reds

Date: December 15, 1900

Giants Got: Christy Mathewson

Reds Got: Amos Rusie

Coming off of a poor season in which they went 62-77, the Reds addressed their most glaring need in the off-season leading up to the 1901 season, trading for veteran starter Amos Rusie.

Rusie had 246 career wins and would one day be a Hall of Famer, but he had not pitched in two seasons and was 30 years old at the time of the deal. In the end, he would do little to solve the Reds' pitching woes, appearing in just three games and posting an 8.59 ERA in 22 innings of work for the Reds before retiring.

Normally, trading for a 30-year-old future Hall of Famer—even if he has not pitched in two seasons—is worth the risk. In this case though, the Reds gave up one of the greatest pitchers in baseball history, sending 20-year-old Christy Mathewson to the Giants in return for Rusie.

Mathewson had appeared in just six games the previous season, with an 0-3 record and a 5.08 ERA. That would all change quickly though, as he went 20-17 with a 2.41 ERA in his first season with the Giants. In all, he would win 373 games and post a miniscule 2.13 ERA over his 17-year career, going down as one of the five greatest pitchers of all time in the process.