The 30 Worst Trades in MLB History

30 Worst Trades in MLB History

Jake Arrieta pumps up his Chicago Cubs teammates | Jared Wickerham/Getty Images

The trading season is never far from the surface in professional baseball. But it will pick back up again as we march ever closer towards spring training 2017. Trades seem to get fans excited — even more so than MLB free agency. Nothing is more fun than seeing your team consider their options, make a smart decision, and pick up a player who you may not have known was even available — all to benefit the franchise’s future.

However, there is danger in building a team through trades. Not only do franchises often have to give up something — or someone — of value in return, but this value may end up being greater than what they received in the first place. Even worse, the player who was so coveted may not live up to his lofty expectations. The fact is, some of the worst trades — even ones that look good on paper — end up disappointing the recipients and all of their fans. These are the 30 worst trades in Major League Baseball history.

1. Lorenzo Cain to the Kansas City Royals

30 Worst Trades in MLB History

Lorenzo Cain smiles at the prospect of a new team | Jamie Squire/Getty Images

The Milwaukee Brewers originally drafted and developed Lorenzo Cain. He first made it to the big leagues 24 years old all the way back in 2010. Cain played in 43 games for the Brewers, hitting well with a .306 batting average and .763 OPS. But that offseason, Milwaukee acquired starting pitcher Zack Greinke from the Kansas City Royals and included Cain, among others, in the deal. Greinke only pitched a year and a half for the Brewers. However, Cain has posted 20.2 WAR over the last four-and-a-half seasons for the Royals.

2. Max Scherzer to the Detroit Tigers

30 Worst Trades in MLB History

Max Scherzer of the Detroit Tigers pitches for a win | Gregory Shamus/Getty Images

In 2009, 24-year-old starting pitcher Max Scherzer had a 4.12 ERA in 30 starts for the Arizona Diamondbacks. Although he demonstrated tantalizing talent, the D-Backs dealt him that offseason in a three-way trade involving the Detroit Tigers and New York Yankees. The Tigers ended up with Scherzer, among others. Arizona traded away the future Cy Young winner for Edwin Jackson and Ian Kennedy — not what we consider a good value.

3. Paul Konerko to the Chicago White Sox

30 Worst Trades in MLB History

(L-R) Chicago White Sox Manager Robin Ventura, White Sox Executive Vice President Kenny Williams, General Manager Rick Hahn, Chairman Jerry Reinsdorf, and a sold-out crowd cheer for Paul Konerko as he is honored during a pre-game ceremony | Brian Kersey/Getty Images

Most people likely don’t remember that Paul Konerko played for teams other than the Chicago White Sox. But he actually was traded twice in the 1998 season. Originally a first-round pick for the Los Angeles Dodgers, Konerko made it to the big leagues in ’98 with LA. Then, he moved to the Cincinnati Reds in a deal for reliever Jeff Shaw. If that weren’t bad enough, the Reds dealt him in the offseason to the Sox in exchange for outfielder Mike Cameron. It’s on our list of worst trades, but it’s not completely terrible; the Reds used Cameron a year later as a centerpiece in the trade that brought them Ken Griffey Jr.

4. Francisco Liriano and Joe Nathan to the Minnesota Twins

30 Worst Trades in MLB History

Joe Nathan of the Detroit Tigers greets teammates prior to the start of Opening Day festivities | Leon Halip/Getty Images

In 2003, Minnesota Twins catcher A.J. Pierzynski was a 4.5 WAR player eyeing the final year of his contract the next season. So, the Twins capitalized on his great season. They traded him to the San Francisco Giants for a package of players, including failed starter Joe Nathan and left-handed pitching prospect Francisco Liriano. Nathan recorded 260 saves for the Twins in seven seasons, while Liriano developed into a quality starting pitcher. The Giants missed the playoffs in ’04 and Pierzynski left to sign with the White Sox.

5. Kyle Hendricks to the Chicago Cubs

30 Worst Trades in MLB History

Kyle Hendricks pitches at Wrigley Field in Chicago | Jon Durr/Getty Images

Back in 2012, the Chicago Cubs were rebuilding, which meant that 35-year-old starting pitcher Ryan Dempster was on the trade market. However, things were complicated due to his no-trade clause. The Cubs had a deal in place for Dempster to go to the Atlanta Braves for pitcher Randall Delgado, but Dempster denied the deal. He later accepted a trade to the Texas Rangers, starting 12 total games for Texas with a 5.09 ERA. The major player the Cubs got in the deal? Starting pitcher and Cy Young candidate Kyle Hendricks.

6. Adam Wainwright to the St. Louis Cardinals

30 Worst Trades in MLB History

Adam Wainwright demonstrates to the Braves that they made a mistake | Rob Carr/Getty Images

Yet another player who’s probably only associated with one franchise, starting pitcher Adam Wainwright was actually drafted by the Atlanta Braves back in 2000. In the winter of 2003, however, the Braves made a move to acquire Cardinals outfielder J.D. Drew and backup catcher Eli Marrero. In return, Atlanta sent reliever Ray King and young starter Jason Marquis. The throw-in on the deal? Pitching prospect Adam Wainwright. The Cubs eliminated the Braves in the NLDS that year. Fortunately, Wainwright has gone on to have an excellent career in St. Louis.

Update 10/4: This article originally placed the Wainwright trade in the midst of the 2003 season, rather than over the winter meetings. It has been updated to correct this error.

7. Vernon Wells to the Los Angeles Angels

30 Worst Trades in MLB History

Vernon Wells of the Los Angeles Angels of Anaheim wipes his forehead after reaching first base | Victor Decolongon/Getty Images

In 2012, outfielder Vernon Wells was coming off an All-Star season in which he posted a .847 OPS and clubbed 31 home runs for the Toronto Blue Jays. But in the offseason, the Jays dealt the slugger to the Los Angeles Angels in return for Mike Napoli. Wells, who was just 32 years old, immediately went into the tank. He posted just a .667 OPS and 0.1 WAR over two years with the Angels; Napoli moved to the Texas Rangers a few days later for reliever Frank Francisco. Napoli posted 7.2 WAR over two seasons in Texas.

8. Bobby Abreu to the Philadelphia Phillies

30 Worst Trades in MLB History

Right fielder Bobby Abreu of the Philadelphia Phillies knocks down a soft fly ball | Doug Pensinger/Getty Images

Back in 1997, the Tampa Bay Devil Rays drafted 23-year-old Houston Astros outfielder Bobby Abreu in the expansion draft. Rather than hold on to the hitting prospect, they immediately dealt him to the Philadelphia Phillies for shortstop Kevin Stocker. Abreu hit 285 more home runs with a .875 OPS and 59.5 WAR over the rest of his career. But Stocker compiled just 2.7 WAR in parts of three seasons in a Devil Rays uniform.

9. Kenny Lofton to the Cleveland Indians

30 Worst Trades in MLB History

Kenny Lofton of the Cleveland Indians runs back to the dugout after making a catch to end an inning | Gregory Shamus/Getty Images

Prior to the 1992 season, the Cleveland Indians and Houston Astros made a swap that appeared to be mutually beneficial. Needing a catcher, the Astros dealt outfield prospect Kenny Lofton to the Indians in return for 22-year-old catcher Eddie Taubensee. But he lasted in Houston just over two seasons, posting a .676 OPS and proving to be a late bloomer with the Cincinnati Reds. Lofton ended up playing 10 total seasons in an Indians uniform. He had 48.5 WAR, five All-Star appearances, and a World Series appearance.

10. Aramis Ramirez to the Chicago Cubs

30 Worst Trades in MLB History

Aramis Ramirez of the Chicago Cubs flips his bat as he watches the flight of his two-run double | Jonathan Daniel/Getty Images

Speaking of Lofton, he was involved in yet another lopsided deal. With a week to go before the 2003 trade deadline, the Cubs made a deal to bolster their lineup and solve their leadoff man issues. They traded Jose Hernandez and infield prospect Bobby Hill to the Pittsburgh Pirates. In exchange, they received Lofton and 25-year-old third baseman Aramis Ramirez. Lofton and Ramirez helped the Cubs advance to the NLCS that year; Ramirez also spent nine years in a Cubs uniform — hitting 239 home runs with a .887 OPS and 23.8 WAR.

11. Joe Jackson to the Cleveland Indians

30 Worst Trades in MLB History -- This work is in the public domain in the United States because it was published (or registered with the U.S. Copyright Office) before January 1, 1923.

Shoeless Joe Jackson of the Cleveland Indians went on to have a prolific MLB career | Source: Wikipedia

Way back in the early 1900s, the Philadelphia Athletics made a big mistake. In the middle of the 1910 season, they made a deal to acquire the immortal Bris Lord, then with the Cleveland Naps (later known as the Cleveland Indians) in exchange for Morrie Rath and Joe Jackson. Lord gave the Athletics a decent 6.6 WAR over three seasons, but Jackson — later nicknamed “Shoeless” Joe Jackson — hit .375/.441/.542 over six seasons in Cleveland.

12. Jose Bautista to the Toronto Blue Jays

30 Worst Trades in MLB History

Jose Bautista of the Toronto Blue Jays throws his bat after he hits a three-run home run against the Texas Rangers in Game 5 of the 2015 American League Division Series | Tom Szczerbowski/Getty Images

Jose Bautista bounced around quite a bit early in his career. He spent time with the Baltimore Orioles, Kansas City Royals, New York Mets, and Pittsburgh Pirates. From 200408, Bautista put together a .722 career OPS with just 46 home runs. The Pirates ended up dealing him to the Toronto Blue Jays. In exchange, they received minor leaguer Robinson Diaz — a move they likely regret. In nine seasons in Toronto since the trade, Bautista has 261 home runs, a .909 OPS, and 37.0 cumulative WAR.

13. Noah Syndergaard to the New York Mets

30 Worst Trades in MLB History

Noah Syndergaard of the New York Mets doesn’t miss his time with the Blue Jays | Mike Stoben/Getty Images

In 2012, the Blue Jays balanced the books with a blunder of their own. Looking for a top-of-the-rotation pitcher, Toronto struck a deal with the New York Mets to acquire 37-year-old Cy Young award-winner R.A. Dickey. The knuckleballer has pitched four seasons in Toronto to date, with a 4.08 ERA in 819 innings. He’s been somewhat of a disappointment, but that’s not the biggest problem with the deal. Noah Syndergaard, current Mets ace and Cy Young award candidate, was the major piece the Mets received in the deal.

14. Lou Brock to the St. Louis Cardinals

30 Worst Trades in MLB History

MLB great Lou Brock greets fans at his National Baseball Hall of Fame ceremony | Jim McIsaac/Getty Images

Another one of the worst trades takes us back to the infamous Lou Brock for Ernie Broglio trade. In Brock, the Cubs had a young and promising outfielder who failed to put things together in the big leagues. In four seasons in Chicago, he had just 3.5 WAR and a .689 OPS. They dealt Brock to their rival, the Cardinals, in exchange for a forgettable pitcher named Broglio. Brock played 16 seasons with the Cardinals, stealing 888 bases with a .761 OPS and 41.6 WAR.

15. Ryne Sandberg to the Chicago Cubs

30 Worst Trades in MLB History

Manager Ryne Sandberg of the Philadelphia Phillies waves to the crowd after winning his first game as a major league manager | Hunter Martin/Getty Images

It’s not as if the Cubs didn’t balance the books on the Brock-Broglio deal, however. Prior to the 1982 season, the Phillies dealt shortstop Larry Bowa and a third-base prospect named Ryne Sandberg to the Cubs in exchange for shortstop Iván DeJesús. Chicago ended up moving Sandberg over to second base, where he won nine Gold Gloves, hit 282 home runs, and developed into a Hall of Fame player. DeJesús played three seasons in Philadelphia, compiling 2.9 WAR.

16. John Smoltz to the Atlanta Braves

30 Worst Trades in MLB History

Pitcher John Smoltz of the St. Louis Cardinals prepares for the 2009 MLB Playoffs | Stephen Dunn/Getty Images

Another name that’s synonymous with a franchise, John Smoltz wasn’t always with the Braves. Smoltz was originally drafted and developed by the Detroit Tigers, but in the middle of the 1987 season they moved him to Atlanta in exchange for pitcher Doyle Alexander. Smoltz came up to the big leagues with the Braves in 1988 and pitched for them as both a starter and a closer through the end of the 2008 season. Smoltz is now in the Hall of Fame, and Alexander got lit up in the postseason that year — allowing 10 earned runs in nine innings in the ALCS.

17. Pedro Martinez to the Boston Red Sox

30 Worst Trades in MLB History

Hall of Fame pitcher Pedro Martinez (L) offers advice to Eduardo Rodriguez of the Boston Red Sox | Jim Rogash/Getty Images

In 1997, Montreal Expos ace Pedro Martinez led the league in ERA at 1.90 and won the National League Cy Young award. The cash-strapped Expos, knowing that 26-year-old Martinez was due for a massive salary raise, shrewdly moved the player at the peak of his career to the Boston Red Sox for a prospect. At least, they thought it was shrewd. Martinez became one of the best pitchers of this generation, winning a World Series in Boston and ending up in the Hall of Fame. The prospect? It was pitcher Carl Pavano, who posted a 4.83 ERA in six seasons in Montreal.

18. Mark McGwire to the St. Louis Cardinals

30 Worst Trades in MLB History

Mark McGwire of the St. Louis Cardinals walks on the field | Elsa Hasch/Allsport/Getty Images

Back in 1997, the Cardinals were coming off a trip to the NLCS and loss to the Atlanta Braves. But they weren’t contending that year, and needed to get an infusion of power into their lineup. They made a deadline deal with the Oakland A’s that did just that, bringing in slugging first baseman Mark McGwire in exchange for spare parts T.J. Matthews, Eric Ludwick, and Blake Stein. Those three didn’t amount to much, but 33-year-old McGwire played five seasons in St. Louis and crushed 220 homers.

19. Cliff Lee to the Cleveland Indians

30 Worst Trades in MLB History

Catcher Will Nieves (L) and pitcher Cliff Lee of the Philadelphia Phillies run off the field | Mitchell Leff/Getty Images

In June 2002, with dwindling attendance and rumors that the franchise may move, the Expos made a deal to keep the team in contention in the NL East. They sent prospects to the Cleveland Indians in exchange for starting pitcher Bartolo Colon. He pitched well for the Expos, who ended up missing the playoffs that year. But unfortunately for Montreal, this deal is all about what they gave up, which includes second baseman Brandon Phillips, outfielder Grady Sizemore, and left-handed starting pitcher Cliff Lee. The latter won a Cy Young award in Cleveland in 2009.

20. Steve Carlton to the Philadelphia Phillies

30 Worst Trades in MLB History

Former Philadelphia Phillies (L-R) Steve Carlton and Tim McCarver stand with Beau Root (McCarver’s grandson) and Brent Musburger before a game | Hunter Martin/Getty Images

A rare blunder made by the Cardinals: dealing Steve Carlton to the Phillies. After seven successful seasons in St. Louis, the Cards sent the 27-year-old lefty to Philadelphia for pitcher Rick Wise after Carlton combined to have a disappointing 3.64 ERA over his final two seasons with the team. The very next year, he led the league in ERA at 1.97 and won the first of four Cy Young awards in a Phillies uniform. Carlton ended up in the Hall of Fame — something that can’t be said for Wise.

21. Jake Arrieta to the Chicago Cubs

30 Worst Trades in MLB History

Jake Arrieta of the Chicago Cubs doesn’t regret moving to his current team | Justin K. Aller/Getty Images

Yet another steal of the Theo Epstein era in Chicago, the Cubs made a deal in 2013 that sent starting pitcher Scott Feldman to the contending Baltimore Orioles in exchange for struggling reliever Pedro Strop and busted pitching prospect Jake Arrieta. Strop turned things around, posting a 2.69 ERA in relief over four years in a Cubs uniform, but the main attraction here is Arrieta. Something clicked, and he went from nearly out of baseball to one of the best pitchers in the big leagues, winning the 2015 National League Cy Young award.

22. Randy Johnson to the Seattle Mariners

30 Worst Trades in MLB History

Randy Johnson of the Arizona Diamondbacks delivers a pitch | Jonathan Daniel/Getty Images

Surprise, surprise; it’s another Expos blunder. In May 1989, Montreal sent tall, erratic left-handed pitcher Randy Johnson to the Seattle Mariners for a sack of nobodies. Johnson had a 6.67 ERA in six starts with the team at the time of the deal, so it didn’t seem to be a mistake at the time. But five Cy Young awards and a World Series trophy later, and it’s clear that the Expos made a bad move in giving up on the fireballer so soon.

23. Derrek Lee to the Chicago Cubs

30 Worst Trades in MLB History

Derrek Lee of the Chicago Cubs waits for a teammate to bring him his hat and glove | Jonathan Daniel/Getty Images

After helping knock the Cubs out of the playoffs in 2003 with the Florida Marlins, the team actually turned around and dealt first baseman Derrek Lee to Chicago in the offseason. In return, they received left-handed hitting first base prospect Hee-Seop Choi. The South Korean slugger had a great but abbreviated ’04 with Florida, hitting 15 home runs with a .882 OPS in 95 games before being moved to the Los Angeles Dodgers and seeing his career fizzle out from there. Lee, on the other hand, hit 179 home runs in seven years with the Cubs and 22.5 WAR, helping lead the team to the postseason in 2007 and 2008.

24. Jeff Bagwell to the Houston Astros

30 Worst Trades in MLB History

Houston Astros first baseman Jeff Bagwell prepares to swing the bat | Jonathan Daniel/Getty Images

Late in the 1990 season, the Boston Red Sox acquired 37-year-old right-handed reliever Larry Andersen from the Houston Astros in exchange for first base prospect Jeff Bagwell. Andersen pitched well for Boston, allowing only three earned runs in 22 innings of work. Bagwell won the Rookie of the Year award in 1991 and MVP in 1994. He also slugged 449 home runs in an Astros uniform over the course of 15 seasons.

25. Willie Hernandez to the Detroit Tigers

30 Worst Trades in MLB History

Guillermo “Willie” Hernandez of the Detroit Tigers | Source: Sully Baseball/Fleer

Prior to the 1984 season, the Phillies dealt unremarkable relief pitcher Willie Hernandez to the Tigers in exchange for Glenn Wilson and John Wockenfuss. Hernandez transformed, leading the American League in games and games finished. He pitched 140 1/3 innings in relief with 32 saves and a 1.92 ERA and was voted both the American League Cy Young winner and the MVP, helping lead the Tigers to win the ’84 World Series. The Phillies finished just 81-81 with a 3.63 ERA from their relievers that year.

26. Keith Hernandez to the New York Mets

30 Worst Trades in MLB History

St. Louis Cardinals Keith Hernandez (L) shakes hands with Hall of Fame manager Whitey Herzog as they celebrate the 30-year anniversary of the 1982 World Series | Paul Nordmann/Getty Images

Keith Hernandez was an All-Star and league MVP in his 10 years with the St. Louis Cardinals, but that all came to an end when they dealt their first baseman to the New York Mets in exchange for pitchers Rick Ownbey and Neil Allen. Both players ended up being nothing more than middle relievers in their short careers with the Cardinals, while 29-year-old Hernandez won five more Gold Gloves and put up 26.5 WAR in a Mets uniform.

27. Josh Donaldson to the Toronto Blue Jays

30 Worst Trades in MLB History

Josh Donaldson is content with the Toronto Blue Jays | Tom Szczerbowski/Getty Images

Third baseman Josh Donaldson developed into an All-Star-caliber player for the Oakland A’s, helping lead the team to the postseason in 2014. But in a move that Billy Beane likely wants to take back, he sent 28-year-old Donaldson to the Blue Jays prior to the 2015 season for Kendall Graveman, Brett Lawrie, and Sean Nolin. Only Graveman is still with the A’s, posting a 4.09 ERA in 49 games the last two seasons. But Donaldson won the American League MVP in 2015 and might be on his way to an award in 2016, as well, accumulating 15.4 WAR in less than two full seasons.

28. Frank Robinson to the Baltimore Orioles

30 Worst Trades in MLB History

Baseball Hall of Famer Frank Robinson throws out the first pitch before an Atlanta Braves game | Patrick Smith/Getty Images

Before the 1966 season, the Cincinnati Reds traded 30-year-old outfielder and former National League MVP Frank Robinson to the Orioles in exchange for pitcher Milt Pappas and two others. While Pappas had a nice career, only three seasons of it came in Philadelphia. Robinson, on the other hand, led the American League in home runs and RBI in ’66, winning the MVP and the World Series. He won the World Series yet again in 1970 with Baltimore.

29. Alex Rodriguez to the New York Yankees

30 Worst Trades in MLB History

Alex Rodriguez celebrates another win with the New York Yankees | Al Bello/Getty Images

In the first three seasons of his then-record-breaking contract with the Texas Rangers, Alex Rodriguez put up astounding numbers. He led the American League in home runs all three years and even won an MVP despite the fact that the Rangers were a pathetic team on the field. Texas decided to cash in on A-Rod’s value after the 2003 season, dealing him to the New York Yankees for second baseman Alfonso Soriano. But Rodriguez was just 28 years old and went on to hit 351 more home runs and win a World Series in a Yankees uniform. Soriano played just two seasons in Texas before being dealt to the Washington Nationals.

30. Babe Ruth to the New York Yankees

30 Worst Trades in MLB History

Babe Ruth of the New York Yankees represents one of the most historic worst trades ever for the Boston Red Sox | Keystone/Getty Images

In what became picturesque of the “bad trade,” the Boston Red Sox dealt away their best player following the 1919 season. Babe Ruth — who had primarily been a pitcher in his career but had just become a full-time hitter at 25 years old — was sent to the New York Yankees in exchange for $100,000, which was a lot of money at the time. Boston famously didn’t win another World Series for 86 years, while the Yankees and Ruth experienced a ton of success. He hit 714 total career home runs and won four more World Series rings in New York.

Follow Ryan on Twitter @RyanDavisBP

Statistics courtesy of ESPN and Baseball-Reference.

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