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The Worst Free Agent Signings in MLB History

Scott Morris | June 20, 2024

Each offseason, MLB teams line up to bid on the top free agents available in the market. Last offseason, it was the Shohei Ohtani sweepstakes. The Dodgers went all-in on baseball’s best player with a 10-year, $700 million contract. Then, Los Angeles added Japanese pitcher Yoshinobu Yamamoto on a 12-year, $325 million deal. 

The results have paid off for the Dodgers. They are 45-29 as of Monday, June 18, and lead the National League West Division by 8.5 games. Ohtani is having another MVP-caliber season. He’s batting .314 (4th in MLB) with 19 HRs (4th), 47 RBIs (14th), and a .988 OPS (4th). Yamamoto is 6-2 with a 2.92 ERA and he has 84 strikeouts in 74 innings. 

These are examples of pretty good free agent pickups. Unfortunately, not all free agent signings end up reaping benefits. Some are just absolute busts. Here are some of the worst.


Milton Bradley – Chicago Cubs

Not to be confused with Milton Bradley the game maker, Bradley had a great season in 2008 in Texas. He led the AL in both on-base percentage and OPS and ended up as the starting DH in the 2008 MLB All-Star game. His success that season led the Cubs to sign Bradley to a three-year, $30 million contract. 

Bradley then started playing games of his own. He made contact with an umpire arguing a strike call. He tossed a routine fly ball into the stands thinking it was the third out of the inning. It was not. Bradley got into it with manager Lou Piniella on a number of occasions and the Cubs finally traded him away after he hit .257 and had 12 HRs the entire 2009 season.

See Milton Bradley’s stat line here


Jacoby Ellsbury – New York Yankees

Jacoby Ellsbury - New York YankeesAfter seven successful seasons in Boston, Ellsbury became a free agent in 2014. The Yankees signed him to a seven-year, $153 million contract with an option year that kicked the value of the deal up to $169 million. Ellsbury would go on to play in 520 of a possible 972 games in his Yankees career. Injuries were his nemesis.

Ellsbury would miss the entire 2018 season with a hip injury and then missed all of 2019 with plantar fasciitis and a shoulder injury. The Yankees released Ellsbury after the 2009 season. Numerous sportswriters and other industry professionals have called Ellsury’s contract the worst free agent signing in Yankees’ history.


Chan Ho Park – Texas Rangers

Yamamoto is not the first Asian pitcher that the Dodgers have signed. In 1994, Chan Ho Park became the first South Korean player to play in an MLB game. He started as a reliever with the Dodgers and by ‘96 was a full-time starter. He went 5-5 with a 3.64 ERA in 1996. In ‘97, he went 14-8 with a 3.38 ERA and appeared to be on an upward trajectory to greatness.

In 2001, which would be his final season in LA, Park went 15-11, had a 3.50 ERA and made the NL All-Star team. At the end of that season, Park would be remembered as the guy that gave up Barry Bonds’ record-breaking 71st and 72nd home runs. Still, his performance as a Dodger would get him a five-year, $65 million deal with Texas.

The Rangers didn’t get their money’s worth. Despite getting one of the larger contracts for a pitcher at that time, Park started 68 games for Texas and left with a 5.79 ERA. 

Mike Hampton – Colorado Rockies

Mike Hampton - Colorado RockiesIf you don’t remember Hampton’s name, don’t worry. You’re not alone. Hampton was drafted by Seattle in 1990. He made his MLB debut in 1993 with the Mariners and then was traded to the Astros before the 1994 season. In 1999, Hampton had his best season with Houston. He went 22-4 with a 2.90 ERA. He was the runner-up for the NL Cy Young award that year, losing out to a guy named Randy Johnson.

Hampton spent the 2000 season with the Mets, going 15-10 with a 3.12 ERA. More importantly, he helped the Mets reach the postseason where he was the MVP of the NLCS. That earned him a hefty 8-year, $121 million contract with the Rockies. It was the largest contract in baseball history at the time (it lasted only two days as Alex Rodriguez would sign his 10-year, $252 million contract with the Rangers). 

In his first year in Colorado, Hampton posted a 5.41 ERA. He then followed that up with a 7-15 season in 2002 with a ridiculous 6.15 ERA. He was traded to Miami, which in turn sent him to Atlanta.

Patrick Corbin – Washington Nationals

Corbin made his MLB debut with the Arizona Diamondbacks in 2012. By 2018, he was an NL All-Star with a 6-3 record and a 3.05 ERA at midseason. He would finish 11-7 with a 3.15 ERA and 245 strikeouts. Corbin became a free agent after the 2018 season and was signed by the Nationals, getting a six-year deal worth $140 million.

In 2019, Corbin would go 14-7 with a 3.25 ERA and lead the Nationals to the World Series. He was the winning pitcher in Game 7 as Washington won its first-ever World Series. Corbin’s 13.89 K/9 in the 2019 playoffs was the third-highest ever.

Since then, it’s been all downhill. His ERA has gone 3.25 in 2019 to 4.66, 5.82, 6.31, 5.20, and is currently 5.84 in 2024. Patrick Corbin Day is an opportunity for bettors to fade Corbin when his turn in the Nats’ rotation is up. This is the final year of his contract. He is 1-7 and will make $35.4 million. Washington can finally dump him after this season.



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