Worst Trades in MLB History

Some baseball general managers should get demoted to the minors after these terrible MLB trades.

Worst Trades in MLB History

Throughout the 150-plus years of Major League Baseball, there have been a number of trades that have set off dynasties, champions or, at the very least, contenders. But there have been just as many baseball trades that have submarined franchises and set them back for years or even decades.

Pulling off a successful trade is both a science and an art as GMs not only look at past performance but also estimate future potential. And unlike other leagues such as the NFL or NBA, draft picks cannot be traded in MLB, so the decision makers really need to do their research on players and prospects. Some have done that, and some have not.

These are the worst trades in MLB history.

30. Padres Trade Anthony Rizzo to the Cubs

Transaction: San Diego trades Rizzo and Zach Cates to Chicago for Kyung-Min Na and Andrew Cashner

Rizzo’s Cubs tenure: 10 seasons (2012-21)

Rizzo with Cubs: 3 All-Stars, 242 HR, 784 RBI

Bottom line: After a dismal showing following a call-up to the majors in which he hit just .141 in 49 games, Rizzo’s tenure ended with the San Diego Padres. Even though he was a top prospect, the club felt he wouldn’t reach his potential, so they shipped him to the Cubs for Andrew Cashner, a 6-foot-6 pitcher who could reach 100 miles per hour.

Rizzo would fully develop in Chicago and become the backbone of the team that ended the Cubs’ World Series drought in 2016. He was a two-way player who hit 30-plus home runs four times with the Cubs while also winning four Gold Gloves at first base.

And while Cashner did hit triple-digits on the radar gun, he also got hit quite often. He was 15 games under .500 in San Diego and never won more than 10 games in a season.

29. Marlins Trade Christian Yelich to the Brewers

Transaction: Miami trades Yelich to Milwaukee for Lewis Brinson, Isan Diaz, Monte Harrison and Jordan Yamamoto

Yelich’s Brewers tenure: 5 seasons (2018-present)

Yelich with Brewers: NL MVP, .294 BA, 101 HR

Bottom line: One of the many roster purges in Marlins history led to a future MVP being dealt for pennies on the dollar. In 2018, the Marlins were going in full rebuild mode, and Christian Yelich preferred to play elsewhere rather than spending his prime on a non-competitive team.

The Marlins acquiesced, but they didn’t get much in sending him to Milwaukee. The prized player they got back was first-round pick Lewis Brinson, but he hit just .199 through his first four MLB seasons.

On the other hand, Yelich’s first four seasons with the Brewers consisted of 101 home runs, two batting titles, an MVP award and an MVP runner-up.

28. Red Sox Trade Jamie Moyer to the Mariners

Transaction: Boston trades Moyer to Seattle for Darren Bragg

Moyer’s Mariners tenure: 11 seasons (1996-2005)

Moyer with Mariners: 145-87 (.625 W-L%), 3.97 ERA, 1,239 K

Bottom line: Despite going 7-1 while floating in between the bullpen and starting rotation for Boston in 1996, the Sox dealt the then 33-year-old Moyer for outfielder Darren Bragg, who was seven years younger. While Bragg had potential, he never became more than a journeyman who had a .255 career average.

Meanwhile, Moyer was traded to Seattle and reinvented himself as an innings-eater finesse lefty. He won 269 career games with over half of those coming in Seattle. Moyer would play until 2012 while Bragg hung up the cleats some eight years earlier, despite, again, being seven years younger.

27. Pirates Trade Willie Randolph to the Yankees

Transaction: Pittsburgh trades Randolph, Ken Brett and Doc Ellis to New York for Doc Medich

Randolph’s Yankees tenure: 13 seasons (1976-88)

Randolph with Yankees: 5 All-Star appearances, 1,731 H, 251 SB

Bottom line: Randolph was one of the best No. 1/No. 2 hitters of the 1970s and '80s and one of the catalysts for two World Series-winning Yankees teams. But he should have never been a Yankee had the Pirates not shipped him out of town while still a rookie. In 1975, the Pirates were coming off getting swept in the NLCS and thought they needed starting pitching help.

Thus, they shipped the 21-year-old Randolph out of town for Doc Medich who would proceed to win all of eight games for Pittsburgh. Randolph would become a five-time All-Star in pinstripes and remains in the top 10 in franchise history for position-player WAR.

26. Pirates Trade Jose Bautista to the Blue Jays

Transaction: Pittsburgh trades Bautista to Toronto for Robinzon Diaz

Bautista’s Blue Jays tenure: 10 seasons (2008-17)

Bautista with Blue Jays: 6 All-Stars, 288 HR, 766 RBI

Bottom line: You could forgive Pittsburgh for giving up on Bautista, as he was a career .241 hitter who never hit more than 16 homers before the deal. But once he was sent to Toronto, Blue Jays’ coaches refined his swing and unleashed the best possible version of Bautista on the baseball world. Bautista went from 13 home runs in 2009 to 54 homers in 2010, and that 39-homer increase is the largest in MLB history. No MLB player hit more home runs than Bautista’s 227 from 2010-15.

In the original transaction, Bautista was sent to Toronto for the infamous “player to be named later.” That would eventually become catcher Robinzon Diaz who played just 44 MLB games after the trade, was then sent back to the minors and never returned to the majors.

25. Yankees Trade Fred McGriff to the Blue Jays

Transaction: New York trades McGriff, Dave Collins, Mike Morgan and cash to Toronto for Tom Dodd and Dale Murray

McGriff’s career: 19 seasons (1986-2004)

McGriff’s stats: 5 All-Stars, 493 HR, 1,550 RBI

Bottom line: The Crime Dog was drafted by the Yankees in 1981, but before he could even play an MLB game in pinstripes, he was dealt for what would amount to essentially nothing. The players the Yankees got in return were pitcher Dale Murray, who would win all of three games after the deal, and batter Tom Dodd, who would collect all of three hits after the trade.

Meanwhile, McGriff would play for six teams, smack nearly 500 home runs and win the 1995 World Series with the Braves. If that wasn’t enough, the Yankees also traded away the second-best and third-best players in the trade in Mike Morgan and Dave Collins, respectively. Morgan would pitch for 19 years after the trade and become an All-Star, while Morgan played eight years and hit .270 after the transaction.

24. Cardinals Trade Steve Carlton to the Phillies

Transaction: St. Louis trades Carlton to Philadelphia for Rick Wise

Carlton’s Phillies tenure: 15 seasons (1972-86)

Carlton with Phillies: 4 Cy Youngs, 241-161 (.600 W-L%), 3.09 ERA

Bottom line: Following a contract dispute, the Cardinals owner ordered the team to trade Carlton, even though he was just 27 and had three All-Star selections under his belt. On paper, this trade seemed like an even swap, but Carlton would go on to become one of the game’s greatest pitchers in Philadelphia, while Wise was essentially an average pitcher for the rest of his career. Wise would make an All-Star Game with the Cardinals, but Carlton would make seven of them in Philadelphia along with winning four Cy Young awards.

"[Cardinals owner] Auggie Busch traded me to the last-place Phillies over a salary dispute," said Carlton, reflecting on the 1992 season. "I was mentally committed to winning 25 games with the Cardinals, and now I had to re-think my goals. I decided to stay with the 25-win goal and won 27 of the Phillies' 59 victories. I consider that season my finest individual achievement."

23. Mariners Trade Omar Vizquel to the Indians

Transaction: Seattle trades Vizquel to Cleveland for Felix Fermin, Reggie Jefferson and cash

Vizquel’s Indians tenure: 11 seasons (1994-2004)

Vizquel with Indians: 8 Gold Gloves, 1,616 H, 279 SB

Bottom line: Vizquel won his first Gold Glove in his final season in Seattle, but the team wanted some extra pop in their lineup. So, they sent Vizquel to Cleveland for fellow shortstop, Felix Fermin, and what they thought was a big bat in Reggie Jefferson. Little did they know that the best was yet to come for Vizquel who would be a three-time All-Star and an eight-time Gold Glove winner with the Indians.

The Mariners thought they were getting equal value at shortstop with Fermin, but he was four years older than Vizquel, and his skills rapidly deteriorated after the trade. He lasted just two seasons with Seattle, which is twice as long as Jefferson stayed in the PNW.

22. Tigers Trade Luis Gonzalez to the Diamondbacks

Transaction: Detroit trades Gonzalez to Arizona for Karim Garcia

Gonzalez’ Diamondbacks tenure: 8 seasons (1999-2006)

Gonzalez with Diamondbacks: 5 All-Stars, .298 BA, 224 HR

Bottom line: Usually when you’re an expansion franchise, you want to build around young players. But the Diamondbacks used a different approach after their inaugural 1998 season, as they traded away 23-year-old Karim Garcia for 31-year-old journeyman, Luis Gonzalez.

Garcia never amounted to much in his MLB career, while Gonzalez became one of the pillars for a World Series-winning team. During the magical 2001 season, he blasted 57 home runs, finished third in MVP voting and helped Arizona win its only major pro sports championship.

21. Astros Trade Kenny Lofton to the Indians

Transaction: Houston trades Lofton and Dave Rohde to Cleveland for Willie Blair and Ed Taubensee

Lofton’s Indians tenure: 5 seasons (1992-96)

Lofton with Indians: .316 BA, 325 SB, 4 Gold Gloves

Bottom line: "I know they gave up on me, and now I'm glad they did,” Lofton said of the Astros. “One man's trash is another man's treasure."

Truer words have never been spoken, as Lofton became one of the best leadoff men of the 1990s in Cleveland, instead of forming a dynamic top-of-the-order with Craig Biggio in Houston. Lofton led the AL in stolen bases all five years of his first stint in Cleveland while also winning four Gold Gloves and being a three-time All-Star. Meanwhile, the two players Houston got back in the trade consisted of a pitcher (Blair) that won all of two games for the team and a catcher that had just 16 hits for Houston.

20. Athletics Trade Jimmie Foxx to the Red Sox

Transaction: Athletics trade Foxx and Johnny Marcum to Boston for Gordon Rhodes, George Savino and $150,000

Foxx’ Red Sox tenure: 7 seasons (1936-42)

Foxx with Red Sox: AL MVP, .320 BA, 222 HR

Bottom line: Finances were the motivation for this trade — why else would the Athletics trade away a 28-year-old who had just won three home run crowns in four seasons? The A’s owner, Connie Mack, was hit hard by the Great Depression and was unable to pay the salary of Foxx and others. Thus, he traded Foxx to the Sox for a pair of players and, most importantly, $150,000, which was over eight times Foxx’s Athletics salary.

Foxx would add a fourth HR crown, win a batting title and win an MVP award in Boston, while Mack just got some deeper pockets.

19. Cubs Trade Ron Santo to the White Sox

Transaction: Cubs trade Santo to White Sox for Ken Frailing, Steve Stone, Steve Swisher and Jim Kremmel

Santo’s White Sox tenure: 1 season (1974)

Santo with White Sox: .221 BA, 5 HR, 41 RBI

Bottom line: This is one of those rare examples of a team trading for a Hall of Fame player but still coming up as the loser in the deal. Ron Santo solidified himself as one of the best third basemen of his era during his 14 years with the Cubs, as he made nine All-Star Games and won five Gold Gloves.

However, he was shipped across town before the 1974 season, and the White Sox got a shell of the player Santo was with the Cubs. He hit just five homers and .221 during his one year with the Sox, while the Cubs got four players in return in the deal, two of which made notable impacts in the majors. Pitcher Steve Stone would win a Cy Young award six years after the trade, albeit with Baltimore, while Steve Swisher would become an All-Star with the Cubs.

18. Senators Trade Early Wynn to the Indians

Transaction: Washington trades Wynn and Mickey Vernon to Cleveland for Joe Haynes, Ed Klieman and Eddie Robinson

Wynn’s Indians tenure: 9 seasons (1949-57)

Wynn with Indians: 163-100 (.620 W-L%), 3.27 ERA, 1,248 K

Bottom line: You know it’s a bad trade when one team trades away their two best players in the deal. That’s what happened to the Senators who sent away future 300-game winner, Early Wynn, as well as a two-time batting champion in Mickey Vernon to Cleveland.

Wynn was the centerpiece, and Cleveland’s pitching staff did something that Washington’s didn’t: They forced him to develop other pitches besides his fastball. That transformed Wynn from a good pitcher into a great pitcher and eventual Hall of Famer. Meanwhile, Washington’s prized return in the trade was first baseman Eddie Robinson who would become a four-time All-Star, but three of those came outside of his time in D.C.

17. Mariners Trade Jason Varitek to the Red Sox

Transaction: Seattle trades Varitek and Derek Lowe to Boston for Heathcliff Slocumb

Varitek’s career: 15 seasons (1997-2011)

Varitek’s stats: 3 All-Stars, 193 HR, 757 RBI

Bottom line: The city of Boston can thank this trade for helping end the 86-year World Series drought for the Red Sox. The transaction landed them to pillars of that championship-winning team in catcher Jason Varitek and pitcher Derek Lowe. Both were multi-time All-Stars with the Sox and combined to form one of the best batteries in the game for a period.

The Mariners motivation for this trade was that they wanted to upgrade their bullpen for a postseason push in 1997. However, acquiring Heathcliff Slocumb wasn’t the answer in doing that, as the reliever went 0-4 in 1997 and then 2-5 in ’98. He also had a 4.97 ERA during his 1.5 years in Seattle.

16. Pirates Trade Aramis Ramirez to the Cubs

Transaction: Pittsburgh trades Ramirez, Kenny Lofton and cash to Chicago for Matt Bruback, Jose Hernandez and Bobby Hill

Ramirez’s Cubs tenure: 9 seasons (2003-11)

Ramirez with Cubs: .294 BA, 239 HR, 806 RBI

Bottom line: Ramirez’s trade is an example of a team growing impatient with a young player despite the obvious talent. Ramirez hit .300 with 34 HRs as a 23-year-old in 2001 for Pittsburgh but could never match those numbers in ensuing seasons. Thus, the Pirates shipped him and speedster Kenny Lofton to Chicago for Jose Hernandez who was nearly a decade older than Ramirez. Hernandez’s best days were behind him, while Ramirez’s best was yet to come, and he proved that in the Windy City. With the Cubs, Ramirez eclipsed .300 four times, had 100-plus RBI four times and hit over 30 home runs three times.

As for Hernandez, he lasted just three months in Pittsburgh and hit .223 before being released by the team.

15. Cubs Trade Lou Brock to the Cardinals

Transaction: Chicago trades Brock, Jack Spring and Paul Toth to St. Louis for Ernie Broglio, Doug Clemens and Bobby Shantz

Brock’s Cardinals tenure: 16 seasons (1964-79)

Brock with Cardinals: 6 All-Stars, 888 SB, .297 BA

Bottom line: It’s one thing to be on the losing end of a lopsided trade, and it’s another to be on the losing end of a lopsided trade to a division rival. The Cubs grew impatient with Lou Brock’s development as a hitter, so they shipped the 25-year-old and spare parts to St. Louis for a deal headlined by pitcher Ernie Broglio who had won 18 games this previous year.

However, Broglio would go just 7-19 in three years with the Cubs, while Brock would become MLB’s stolen base king in St. Louis. Brock would also help the Cardinals win a World Series championship just four months after the trade, and he won another with the Cards three years later.

14. Red Sox Trade Tris Speaker to the Indians

Transaction: Boston trades Speaker to Cleveland for Sad Sam Jones, Fred Thomas and $55,000

Speaker’s Indians tenure: 11 seasons (1916-26)

Speaker with Indians: .354 BA, 1,965 H, 886 RBI

Bottom line: In 1914, Speaker hit .338, and the next year he hit .322. Despite his average dropping just .016 points, Boston’s president asked Speaker to take a 40 percent pay cut due to his dip in average. Speaker refused and, thus, was traded to Cleveland for a pair of players and, more importantly, $50,000 in cash.

Speaker proved Boston wrong by not only increasing his average in his first year in Cleveland but by leading the majors with a .386 average. He would hit over .350 during his 11 years with the Indians and remains MLB’s all-time leader in doubles (792).

13. Astros Trade Joe Morgan to the Reds

Transaction: Houston trades Morgan, Ed Armbrister, Jack Billingham, Cesar Geronimo and Denis Menke to Cincinnati for Tommy Helms, Lee May and Jimmy Stewart

Morgan’s Reds tenure: 8 seasons (1972-79)

Morgan with Reds: 2 NL MVPs, 8 All-Stars, 406 SB

Bottom line: Morgan was the prototypical top-of-the-order hitter who had great speed and a high on-base percentage. But the Astros wanted more power in their lineup, so they dealt him and others to Cincinnati for a package headlined by slugger Lee May.

While May did go on to hit over 350 HRs in his career, Morgan became a Hall of Famer and a critical cog to the Big Red Machine dynasty of the Reds. Furthermore, the others that Cincinnati received in the trade were also key contributors, as Billingham made an All-Star team with the Reds and won two World Series games, while Geronimo was a four-time Gold Glove winner in Cincy.

12. Athletics Trade Mark McGwire to the Cardinals

Transaction: Oakland trades McGwire to St. Louis for Eric Ludwick, T.J. Mathews and Blake Stein

McGwire’s Cardinals tenure: 5 seasons (1997-2001)

McGwire with Cardinals: 3 All-Stars, 220 HR, 473 RBI

Bottom line: McGwire was unhappy playing for the losing A’s and was set on becoming a free agent at the end of the 1997 season, so Oakland really had no choice but to trade him. That’s understandable, but what Oakland got in return in the transaction was not. Two of the players – Eric Ludwick and Blake Stein – won a total of six games in an A’s uniform, while the prized possession in the deal, T.J. Mathews, never reached his potential. Mathews posted a 2.53 ERA across four seasons in St. Louis but that ballooned to a 4.78 ERA across five years in Oakland.

We all know what McGwire did after the trade, as he broke Roger Maris’ single-season home run record. His 1998 season helped bring baseball back into the spotlight after the 1994 strike, even if his season comes with an asterisk.

11. White Sox Trade Sammy Sosa to the Cubs

Transaction: White Sox trade Sosa and Ken Patterson to Cubs for George Bell

Sosa’s Cubs tenure: 13 seasons (1992-2004)

Sosa with Cubs: NL MVP, 545 HR, 1,414 RBI

Bottom line: Sosa was dealt from the South Side to the North Side for aging slugger George Bell, who won the AL MVP in 1987 but was past his prime by 1992. Sosa had shown promise for the White Sox, as he had double-digit homers and steals in both his seasons with the team, but the Sox grew impatient with his development.

Thus, the Cubs were the benefactors, and Sosa would become an NL MVP and two-time home run champion with the Cubbies. As for Bell, he led the AL in grounded-into-double-plays in 1992, hit .217 in 1993 and was out of the majors by 1994.

10. Reds Trade Frank Robinson to the Orioles

Transaction: Cincinnati trades Robinson to Baltimore for Jack Baldschun, Milt Pappas and Dick Simpson

Robinson’s Orioles tenure: 6 seasons (1966-71)

Robinson with Orioles: AL MVP, .300 BA, 179 HR

Bottom line: After a decade of stellar play, six All-Star teams and an MVP, Robinson was undervalued by Reds owner Bill DeWitt. Thus, Dewitt dealt him to Baltimore, and afterward, he called the 30-year-old Robinson, “not a young 30.” But the best of Robinson was still yet to come, as in his first season with the Orioles, all he did was win the AL Triple Crown, win another MVP and lead Baltimore to a World Series title.

As for the players DeWitt and the Reds got in return? None of the three even lasted three seasons with the Reds, and none of them ever made an All-Star Team after the trade.

9. Phillies Trade Ryne Sandberg to the Cubs

Transaction: Philadelphia trades Sandberg and Larry Bowa to Chicago for Ivan de Jesus

Sandberg’s Cubs tenure: 15 seasons (1982-94, 1996-97)

Sandberg with Cubs: 10 All-Stars, 9 Gold Gloves, 282 HR

Bottom line: Sandberg was blocked from getting meaningful playing time in Philadelphia, so they dealt him to Chicago for shortstop Ivan de Jesus. But had the Phillies known Sandberg would develop into an MVP-winning second baseman, then they would have likely traded away the player who was blocking Sandberg from that meaningful playing time.

As for de Jesus, he spent three years in Philly and never hit above .257 in any season. He also hit as many homers (seven) for the Phillies as Sandberg had Silver Slugger awards for the Cubs.

8. Red Sox Trade Jeff Bagwell to the Astros

Transaction: Boston trades Bagwell to Houston for Larry Anderson

Bagwell’s career: 15 seasons (1991-2005)

Bagwell’s stats: .297 BA, 449 HR, 1,529 RBI

Bottom line: What makes this trade so egregious is that not only did Bagwell become a Hall of Famer and one of the greatest first basemen of all time, but he also was a New England native who was born in Boston.

But the Red Sox desperately wanted some relief help in their 1990 postseason push, so they gave up Bagwell, who was in the minors at the time, for Anderson. The 37-year-old pitcher would throw all of 22 innings for the Sox, while Bagwell would become the greatest player in Astros history.

7. White Sox Trade Fernando Tatis Jr. to the Padres

Transaction: Chicago trades Tatis Jr. and Erik Johnson to San Diego for James Shields

Tatis Jr.’s career: 4 seasons (2019-present)

Tatis Jr.’s stats: .292 BA, 81 HR, 52 SB

Bottom line: Despite having a 3-6 postseason record, James Shields was nicknamed Big Game James. Well, the White Sox felt they needed a theoretically clutch pitcher in order to help with their 2016 postseason push, so they gave up a 17-year-old with superstar potential in order to acquire Shields. The pitcher then proceeded to post an unsightly 16-35 record in Chicago with a 5.31 ERA, and the White Sox never qualified for the postseason in any of his three seasons with the team.

As for that the then-17-year-old, he’s lived up to the billing and has become one of the current faces of MLB. He led the majors in homers in just his third year, has 40/40 potential and has multiple top-five MVP finishes … all by the age of 22.

6. Expos Trade Pedro Martinez to the Red Sox

Transaction: Montreal trades Martinez to Boston for Carl Pavano and Tony Armas Jr.

Martinez’s Red Sox tenure: 7 seasons (1998-2004)

Martinez with Red Sox: 2 Cy Youngs, 117-37 (.760 W-L%), 2.52 ERA

Bottom line: In 1997, a 25-year-old Pedro Martinez went 17-8 with a league-leading 1.90 ERA and won the NL Cy Young. So, how did the Expos reward their prized pitcher? They traded him in the offseason to Boston because they feared Martinez would walk in free agency. That’s understandable, but what the Expos got in return in the trade is not.

Pavano went just 24-35 with Montreal and didn’t break out until after he left the team, as he became an All-Star with the Marlins. As for Armas Jr., he is the son of former slugger Tony Armas who was a two-time home run champion in the 1980s. However, Junior was not a chip off the old block and not just because he was a pitcher instead of a hitter. The ability that the elder Armas had at the plate didn’t carry over to the younger Armas on the mound, as he posted a 4.45 ERA during his eight-year career with the Expos/Nationals franchise.

5. Tigers Trade John Smoltz to the Braves

Transaction: Detroit trades Smoltz to Atlanta for Doyle Alexander

Smoltz’s career: 21 seasons (1988-99, 2001-09)

Smoltz’s stats: 213 W, 154 SV, 3,084 K

Bottom line: In a classic example of a team only focusing on the short-term, the Tigers traded a 20-year-old Smoltz — who was a Detroit native — for a 36-year-old Doyle Alexander. While Alexander did help the Tigers by going 9-0 down the stretch, Smoltz would become a pillar of the 1990s Braves dynasty. He is the only player in MLB history with 200 wins and 150 saves, won a World Series in 1995, a Cy Young in 1996 and had a sterling 15-4 postseason record.

On the other hand, Alexander faded after his hot start, as he went 20-29 over his last two years in Detroit and retired after the 1989 season.

4. Marlins Trade Miguel Cabrera to the Tigers

Transaction: Florida trades Cabrera and Dontrelle Willis to Detroit for Dallas Trahern, Burke Badenhop, Frankie De La Cruz, Cameron Maybin, Andrew Miller and Mike Rabelo

Cabrera’s Tigers tenure: 15 seasons (2008-present)

Cabrera with Tigers: 2 AL MVPs, .309 BA, 364 HR

Bottom line: What do you do with a 24-year-old with four All-Star Games and a .313 career batting average under his belt? If you’re the Marlins, you trade away one of the faces of MLB because you’re worried he’ll demand too much in salary. That’s what the Marlins did to Miguel Cabrera who would go from one of the game’s rising stars in Florida to one of the game’s superstars in Detroit.

Cabrera won four batting titles, two MVPs and a Triple Crown in the Motor City, while the Marlins’ return was downright embarrassing. Maybin and Miller were the only players that the Marlins got who made an impact in MLB, and those came well after they had already left Miami.

3. Expos Trade Randy Johnson to the Mariners

Transaction: Montreal trades Johnson, Gene Harris and Brian Holman to Seattle for Mark Langston and Mike Campbell

Johnson’s Mariners tenure: 10 seasons (1989-98)

Johnson with Mariners: 130-74 (.634 W-L%), 3.42 ERA, 2,162 K

Bottom line: The Expos liked Randy Johnson’s strikeout potential, but they were in love with Mark Langston who had already been an All-Star and Gold Glove winner on the mound. Thus, Montreal sent a package of players to the Mariners for Langston who didn’t disappoint over the span of his career, as he won seven Gold Gloves and four All-Star teams. However, none of that came in Montreal, spending just six months with the team before departing as a free agent.

Johnson would go on to become one of the most menacing pitchers of all time, with Seattle seen as the launching pad of his career. With the Mariners, he was a five-time All-Star, a four-time strikeout champion and won the first of his five Cy Young awards.

2. Padres Trade Ozzie Smith to the Cardinals

Transaction: San Diego trades Smith, Steve Mura and Al Olmsted to St. Louis for Sixto Lezcano, Garry Templeton and Luis Deleon

Smith’s Cardinals tenure: 15 seasons (1982-96)

Smith with Cardinals: 11 Gold Gloves, 1,944 H, 433 SB

Bottom line: There’s often another party involved when a player and a team don’t get along, and that’s the agent. Smith’s agent wasn’t happy with his client’s contract in San Diego and mockingly took out a help-wanted ad in a local newspaper that read “Padre baseball player wants part-time employment to supplement income.”

That angered the Padres’ front office so much that they were willing to trade Smith to St. Louis. But emotions got the best of them, as they sent away the best player in the deal. Smith would become arguably the greatest defensive player in MLB history with the Cardinals. Meanwhile, the prized return for San Diego was Garry Templeton who would spend a decade with the Padres but made just one All-Star Game.

1. Red Sox Trade Babe Ruth to the Yankees

Transaction: Boston trades Ruth to New York for $100,000

Ruth’s Yankees tenure: 15 seasons (1920-34)

Ruth with Yankees: .349 BA, 659 HR, 1,978 RBI

Bottom line: After leading baseball in home runs in both 1918 and 1919, Babe Ruth justly wanted a raise. But his then-owner, Harry Frazee of the Red Sox, was a theatrical owner on the side, and he also needed money. Thus, Frazee sold Ruth to the Yankees for $100,000, so the slugger could get the money he wanted and Frazee could get funding for his plays and musicals.

It turned out to be the worst transaction in MLB history, as Ruth skyrocketed into fame and became a cultural icon in New York. His impact was felt on the field, as he became baseball’s Home Run King, and in the minds of people as the Yankees would become MLB’s signature franchise. The Yankees would go on to win 27 World Series championships — four of them with Ruth in pinstripes, while the Red Sox’s fortunes also changed. After winning five of the first 16 World Series championships before the trade, Boston would have to wait almost 86 years before it won its sixth World Series title.