These are the worst MLB free-agent signings ever

Mackenzie MeaneyMackenzie Meaney|published: Sat Dec 30 2023 19:11
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The media and fans (not so) patiently waited for the two biggest free agents — Shohei Ohtani and Yoshinobu Yamamoto — to sign new deals with new teams. The American League MVP and the 25-year-old ace both inked pacts with the Los Angeles Dodgers, who have spent more than $1 billion so far this offseason.

Ohtani is coming off of surgery, and Yamamoto has never pitched in the MLB, but the Dodgers went all in on 10-, and 12-year deals, respectively, for the Japanese superstars. It will take some time to see how well the deals age, but with the benefit of hindsight, we’ve compiled a list of free-agent signings that were total busts.

Here they are.

Mike Hampton, Colorado Rockies (2001-2002)

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The lefty was the National League Cy Young runner-up in 1999, and was the 2000 NLCS MVP, which put him in line for a payday.

Hampton received what at the time was the largest contract in baseball history — eight years, $121 million — though it was surpassed by A-Rod’s pact with Texas two days later.

Hampton, who once claimed he joined the Rockies for Colorado’s school systems, posted a 5.41 ERA in his first season in the Mile High City. He followed that up with a 6.15 ERA and was shipped to Miami, who flipped Hampton to Atlanta.

Pablo Sandoval, Boston Red Sox (2015-2017)

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Coming off a strong performance in the World Series, Kung Fu Panda landed a five-year, $90 million deal from the Boston Red Sox. Sandoval posted career lows in his first season in Beantown, and spent most of his tenure there on the IL, and eventually made his way back to the San Francisco Giants.

Chan Ho Park, Texas Rangers (2002-2005)

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Chan Ho Park is both the first South Korean to play in the MLB, and the owner of the most career wins of any Asia-born pitcher in history.

He’s also one of the worst free-agent signings. He made 68 starts over his time in Texas and compiled a 5.79 ERA.

Russ Ortiz, Arizona Diamondbacks (2005-2006)

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Things were so bad for Ortiz in the desert that Arizona released him during the second year of his four-year, $33 million deal. He made 28 starts, and put up some ugly numbers: 7.00 ERA, 1.896 WHIP, and 5.7 BB/9.

Josh Hamilton, Los Angeles Angels (2013-2014)

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Two years removed from his MVP season with the Texas Rangers, Hamilton inked a five-year, $125 million deal with the Angels. Sadly, Hamilton suffered various injuries and relapsed while recovering from shoulder surgery. He was dealt back to the Rangers and L.A. ate roughly $62.5 million of his contract.

Jacoby Ellsbury, New York Yankees (2014-2017)

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Ellsbury’s tenure in the Bronx was marred by injuries. He played in only 520 of 972 possible games before the Yankees released him from his seven-year, $153 million contract.

It was a huge overpay, and Yankee blog Pinstripe Alley dubbed his contract the worst in franchise history.

Albert Belle, Baltimore Orioles (1999-2000)

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Some things in life you just can’t control, like having a degenerative hip condition.

That’s what happened to Albert Belle, who signed a contract with Baltimore in 1998 that called for five years for $65 million. He had a unique clause in his previous contract with the White Sox, where if he wasn’t one of the top three highest earners in the league, he could opt out and go wherever he wanted. The deal from the Orioles tied him with Mike Piazza for third in the league in highest earnings, but he could only play for two years.

Carl Pavano, New York Yankees (2005-2008)

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You know it’s bad if your teammates start to call you out.

After winning a World Series with the Marlins in 2003, Pavano made his way to the Bronx on a four-year, $39.95 million deal. He was injured most of the 2006 season, and after his return, teammate Mike Mussina however, thought that Pavano did not perform like he wanted to be a Yankee and he needed to prove himself. He is also most well known during his time as a Yankee for his “ bruised buttocks” injury.

Jason Bay, New York Mets

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What a disaster. Things were so bad for Bay in Queens that the Mets terminated the oft-injured outfielder’s four-year, $66 million deal a year early.

Milton Bradley, Chicago Cubs

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Only a Cubby for one season, Bradley was brought on with a three-year, $30 million contract. He was probably the most unfriendly person in the friendly confines of Wrigley Field.

He made contact with an ump while arguing a called strike, “went after” a Gatorade cooler in the dugout, and flipped off Rangers fans.

In addition to seeing his numbers drop off after his first-ever All-Star selection, Bradley threw a live ball into the stands after making an out.

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There’s even a compilation on YouTube of all the outfielder’s ejections.


Bradley was dumped to Seattle where he finished out his career.