The 20 Worst Free-Agent Signings in MLB History (And What They Cost)

Baseball has been littered with bad contracts, and these are some of the worst in MLB history.

Stephen Strasburg's $245 million contract turned bad in record time for the Washington Nationals. Mandatory Credit: Tommy Gilligan-USA TODAY Sports / USA TODAY Sports

Judge a contract by Major League Baseball standards can be done pretty simply: how did that particular player contribute to winning? Consider Patrick Corbin's six-year, $140 million contract with the Nationals just before the 2019 season. He was awful for the majority of that deal, but his impact on their World Series run erases those bad memories, and if we went back in time Nats fans would absolutely make that move again.

Washington Nationals starting pitcher Patrick Corbin (46) holds the trophy at the World Series Championship Parade. / USA TODAY Sports

The deals on this list, however, contributed little beyond the player and their agent coming out of it handsomely paid. You can't fault a player for getting their bag, but these deals aged terribly for the teams, sometimes shockingly quickly.

Whatever that cause was, here are 20 of the worst contracts in MLB history. Maybe you have a personal favorite, and hopefully that brings back fond memories for you.

20. A bad pitcher is still bad: Jeff Suppan, Milwaukee Brewers (4 years, $42 million in 2007)

In five years with the Kansas City Royals, he had a 4.73 ERA. For some reason, the Brewers thought they were going to get something a little different, but in the end, in his four years there, he accumulated a 5.08 ERA.

This wasn't the biggest deal on this list as far as money goes, but the Brewers essentially lit $42 million on fire here. It wasn't like today's game, where teams see something in a pitcher, tinker with them, and then they find a new gear. Take Gerrit Cole when the Astros acquired him from the Pirates. Suppan was just bad and remained so here.

19. A bad deal right from the start: Jordan Zimmermann, Detroit Tigers (5 years, $110 million in 2016)

Jordan Zimmermann was one of the more dependable arms in baseball when the Detroit Tigers signed him. In seven years with the Nationals, he had a 3.32 ERA in 1,094 IP. Things were different while with Detroit, though.

He came apart fast due to injury, and when he did play, he was simply ineffective. In five years with the Tigers, he had a 5.63 ERA in 514.1 IP. In 2017, he led MLB with 108 earned runs.

18. The scoreboard destroyer: Mo Vaughn, Los Angeles Angels (6 years, $80 million in 1999)

Mo Vaughn had prodigious power and played through some lean years in Boston before the organization started to really put it together. He got MVP votes every year between 1993 and 1998, and so the Angels thought they were adding a real power threat to their lineup.

He wasn't bad, either. He hit .276/.362/.503 while he was there, but the one red flag was the strikeouts. In 2000, he led the league with 181 strikeouts, and after being injured in 2001 and missing the entire year, he was traded to the Mets.

By the time Vaughn went to New York, it was clear that the defense was gone. Unfortunately for him, the DH was still decades away from heading to the NL. Vaughn had an .805 OPS in year one with the Mets, and that fell to .652 during an injury-plagued 2003.

His time with the Mets wasn't anything special, but he will always be remembered for hitting the scoreboard at Shea Stadium in 2002. Not many had the power to do that in a stadium known as a pitcher's park.

6/26/2002 Mo Vaughn hits one of the longest home runs in Shea Stadium history, a 505-foot blast that hits halfway up the scoreboard in right-center field. pic.twitter.com/1dbM7htuuK

— This Day in Mets History (@NYMhistory) June 26, 2025

17. A tall order: Richie Sexson, Seattle Mariners (4 years, $50 million in 2005)

His tenure in Seattle started with a bang, with back-to-back 30+ home run seasons. Then things began falling apart in 2007. He played in 121 games and hit .205/.295/.399 in 2007, and when he didn't rebound in 2008, the Mariners cut him loose. Sexson went on to play for the Yankees, but they cut him loose after 22 games.

16. All bat and no glove: Yasmany Tomás, Arizona Diamondbacks (6 years, $68.5 million in 2014)

The Diamondbacks thought they were getting a cornerstone player when they signed Yasmany Tomás out of Cuba. He had one good season at the plate, hitting 31 homers with an .820 OPS in 2016, but somehow finished with a -.5 WAR that season due to his defense. Tomás had a staggering -17 Outs Above Average that year and was also a poor base runner.

After that season, Tomás only played another 51 games between 2017 and 2019. He was a one-hit wonder, and his one hit wasn't even all that valuable to Arizona.

15. The Triple-A Superstar: Rusney Castillo, Boston Red Sox (7 years, $72.5 million in 2014)

Rusney Castillo, the former international signing out of Cuba, was considered a five-tool player. Unfortunately, he was more productive in Triple-A. He reached as high as No. 21 on Baseball America's Top 100 Prospects list.

While in the minors, he hit .293/.335/.425. In 99 big-league games across three seasons, he hit .262/.301/.379.

Castillo last played baseball in 2025. When the big leagues looked like they weren't happening for him, he made a stop with the Long Island Ducks and finished out his career in Mexico.

14. A panda and a green monster aren't meant to co-exist: Pablo Sandoval, Boston Red Sox (5 years, $95 million in 2015)

Pablo Sandoval might be the only person on this list who may have been benched for using Instagram during a game. For Sandoval, it was more pressing for him to like a random woman's pictures than it was to produce on the field for Boston. Ask Jared Carrabis, and Sandoval may be his least favorite player to have ever suited up for his Sox.

Carrabis probably has years' worth of ammo against him, too, seeing as Sandoval hit .237/.286/.360 in over three years in Boston. Panda's best years were in San Francisco, and he didn't quite bring that same flair to Beantown.

13. Give credit to Boras for this one: Eric Hosmer, San Diego Padres (8 years, $144 million in 2018)

The Eric Hosmer contract was a Scott Boras masterclass, in which the Padres essentially paid for what Hosmer did with the Kansas City Royals. Over five years in San Diego, Hosmer posted an okay slash line. He hit .265/.325/.411, but okay wasn't what they were paying for.

They ended up trading him to Boston after agreeing to cover most of the deal's cost. He spent a half-season there before joining the Cubs before eventually retiring after the 2023 season. He is a great follow on X, though. One of the nicest, most accessible athletes on there.

San Diego Padres first baseman Eric Hosmer (30) looks back after hitting an RBI double during the sixth inning against the New York Mets at Citi Field. / USA TODAY Sports

12. Didn't like his move to San Francisco: Willy Adames, San Francisco Giants (7 years, $182 million in 2025)

Willy Adames was one of the premier shortstops in baseball while with the Milwaukee Brewers, and had a big walk season. The Giants thought they were getting a player in their prime when they signed him, but he has progressively gotten worse in his first two seasons with the Giants.

Adames had a 108 wRC+ with a 4.1 WAR, according to FanGraphs. Things aren't looking much better this season. At least Adames has until 2031 to turn things around, though.

11. The Mets are happy to have lost this arms race: Trevor Bauer, Los Angeles Dodgers (3 years, $102 million in 2021)

File this one under the Mets dodging a bullet here, too. The Mets and Dodgers were the finalists for Bauer's services before the 2021 season, and he ultimately chose Los Angeles. Not that it mattered, anyway. Bauer pitched all of 107.2 innings in Dodger Blue before being suspended under the MLB's domestic violence/sexual assault policy and he's never pitched in the big leagues since.

The Dodgers aren't on the hook for some of that money, though. And while some swear up and down that he's still an ace, he didn't finish out his season with the Long Island Ducks. Now he's back in Mexico.

10. At least the weather is nice in San Diego: Xander Bogaerts, San Diego Padres (11 years, $280 million in 2023)

The Boston Red Sox have always been good at letting players go before they fall off a cliff. Case in point with Xander Bogaerts. A once-staple of two championship teams, the shortstop signed a big-money deal in San Diego only to fail to live up to expectations.

In four years, Bogaerts has hit .261/.328/.390. He's getting on base at a decent clip, but the power has been close to non-existent.

San Diego Padres shortstop Xander Bogaerts against the Arizona Diamondbacks at Chase Field. / IMAGN IMAGES via Reuters Connect

9. The Colorado school system tipping the scales: Mike Hampton, Colorado Rockies (8 years, $121 million in 2001)

If you were to ask Mike Hampton why he chose the Rockies over the Mets after an excellent season where he helped bring them to a World Series, it was because of the school district. It had nothing to do with money.

Mets fans may not have loved the excuse, but they were at least off the hook from watching their team pay him thereafter. Following that excellent 2000, Hampton posted a 4.84 ERA over his next 1,007.2 innings pitched.

8. Paying him to go away: Jacoby Ellsbury, New York Yankees (7 years, $153 million in 2014)

It was clear that Robinson Cano wasn't coming back. In what could have been a move to save face, the Yankees ended up shelling out big money to Jacoby Ellsbury, whose contract became an eyesore pretty fast.

Ellsbury was okay his first season in the Bronx, but considering the money, okay doesn't hack it. He hit .271/.328/.419 in 2014, and by his final season in New York, 2017, he was essentially a backup, and the Yankees couldn't wait to get rid of him.

The Yankees attempted to void the contract at the end, citing the fact that he received medical help outside the organization, but the two parties ultimately settled. The dispute didn't hurt the relationship between Scott Boras and the Yankees, though. They've since done business with Gerrit Cole and Cody Bellinger.

7. That isn't wind, it's another whiff: Javier Báez, Detroit Tigers (6 years, $140 million in 2022)

Javier Báez
Detroit Tigers
2022: 6 years, $140 million

Báez was a part of that illustrious shortstop class of 2022. He brought his glove to Detroit in his first season, with a 1 OAA. The issue was that 47.5% chase rate on pitches outside the zone as an introduction to his new team. Báez consistently had chase rates in the 40% range, and no ball is too far out of the zone for him to swing at.

6. And for our next trick... We'll make a superstar disappear: Kris Bryant, Colorado Rockies (7 years, $182 million in 2022)

Kris Bryant went from the handsome face of the Chicago Cubs to pulling off one of the great Houdini acts of our time after signing with the Colorado Rockies. Since 2022, Bryant has only played in 170 games. He hit .244/.324/.370. Maybe one day he'll return just as King Odysseus did.

5. Arte Moreno masterclass: Josh Hamilton, Los Angeles Angels (5 years, $125 million in 2012)

Maybe Arte Moreno's money is cursed? The Angels thought they were adding a former MVP. Instead, they got a player who couldn't stay on the field, and by the time Josh Hamilton's tenure ended, they sent him back to Texas. They still had to pay him, too.

Hamilton hit more home runs in 2012 (43) than he did in Los Angeles (31) as a whole. Just like the rest of us, the Angels can look back fondly on his Home Run Derby performance. Of course, it wasn't with them. Every time the Angels pay someone, they're always paying for what a player did elsewhere.

4. Falling off of a cliff in Baltimore: Chris Davis, Baltimore Orioles (7 years, $161 million in 2016)

Chris Davis
Baltimore Orioles
2016: 7 years, $161 million

When the Orioles paid Chris Davis, it felt like a move they had to make. Nelson Cruz, Nick Markakis and Andrew Miller all left in free agency, and they felt like they couldn't let another team staple go—especially someone with the power that Davis had.

Davis went from getting MVP votes before signing that deal to then becoming one of the worst hitters in the sport. Between 2016 and 2020, he hit .196/.291/.379.

Davis announced his retirement from baseball due to a chronic hip injury, and because of deferred payments, the Orioles will pay him until 2037. It was the baseball version of a bad Klarna purchase.

Baltimore Orioles first baseman Chris Davis (19) throws the ball to home plate in the tenth inning against the Toronto Blue Jays at Oriole Park at Camden Yards. / USA TODAY Sports

3. Maybe the Angels are cursed: Albert Pujols, Los Angeles Angels (10 years, $240 million in 2012)

Albert Pujols was one of the best players on the planet in the early 2000s with the St. Louis Cardinals. That NLCS homer against Brad Lidge still hasn't landed, and it was such an illustrious shot that it broke the closer for a few years.

Pujols with the Angels is unfortunately a different story. He hit .256/.311/.447 in 1,181 games. Funny enough, things looked up once he left, so maybe it was the Angels.

He had a .759 OPS with the Dodgers. He then had that huge year with the Cardinals, posting an .895 OPS before retiring.

2. The worst of the bad Angels contracts: Anthony Rendon, Los Angeles Angels (7 years, $245 million in 2020)

Anybody watching the World Series in 2019 never could have believed how much Rendon's production would fall off. Rendon's best season came during the pandemic-shortened 2020 season, and, funny enough, that was the third-most games he played with the Angels.

His most significant highlight probably came when he hit a ball left-handed. Angels fans will always have that.

1. Breaking down before the ink dried on the deal: Stephen Strasburg, Washington Nationals (7 years, $245 million in 2020)

Coming off that 2019 World Series, Stephen Strasburg was a hero. He came into the league as one of the biggest pitching prospects in the sport, and finally delivered Washington a World Series.

He and Gerrit Cole were up for big paydays just before the 2020 season began, and he was the first significant pitching piece off the board. After leading the National League in innings before his big payday, Strasburg pitched all of 31.1 innings between 2020 and 2022 before calling it a career. What he brought to the Nationals organization will never be forgotten, but his second deal after his extension is one of the worst in recent memory.