Top 3 Worst Free Agent Signings in Yankees History

Fresh off another ALCS exit, the New York Yankees turn their attention to the offseason, where the most significant priority will be re-signing star free-agent slugger Aaron Judge. 

While Judge has earned a substantial payday, free agency has not been kind to the Bronx Bombers, with several big money deals turning into colossal nightmares.

Here are the worst of the worst, starting with 2004’s “prized” acquisition.

3) SP Carl Pavano – Four Years, $39.95 Million

Pavano enjoyed a career season in 2004 while a member of the Florida Marlins, posting an 18-8 record and a 3.00 ERA across 222.1 innings (31 starts). He was able to parlay those numbers into a four-year, $39.95 million contract with the Yankees during the offseason. 

However, things did not go according to plan. Injuries marred Pavano’s tenure. After recording a 4.77 ERA in 17 starts in his first season in the Bronx, the former All-Star did not pitch in 2006 before undergoing Tommy John Surgery in May 2007.

Disappointing on the mound, Pavano was not well-liked by all in the clubhouse, as evidenced by veteran starter Mike Mussina, who questioned the former’s desire to pitch in Pinstripes. Speaking about Pavano’s injuries, Mussina said, “It didn’t look good from a player’s and teammate’s standpoint. Was everything just a coincidence? Over and over again? I don’t know.”

Pavano would appear in 26 games for the Yanks, pitching to a 5.00 ERA, not the high-level starter New York was banking on.

2) SP Kei Igawa – Five Years, $20 Million

After striking out on pitcher Daisuke Matsuzaka, Yankees general manager Brian Cashman was confident he had landed the next best thing in fellow Japanese hurler Kei Igawa. New York agreed to pay a $26 million posting fee before signing Igawa to a five-year, $20 million deal on November 29, 2006.

Igawa was overmatched at the big league level, recording an ugly 6.66 ERA in 16 appearances. He failed to make the team out of spring training in 2008, finishing the remaining years of his contract in the minor leagues.

If there is a silver lining for Yankees fans, it’s that Matsuzaka, who landed with arch-rival Boston Red Sox, did not light the MLB world on fire, posting a 4.52 ERA across six seasons in Beantown.

1) Jacoby Ellsbury – Seven Years, $153 Million

Expectations were running high ahead of the 2014 campaign when the Yankees lured star centerfielder Jacoby Ellsbury away from the Boston Red Sox, signing him to a massive seven-year, $153 million contract.

Unfortunately, Red Sox fans would have the last laugh as Ellsbury was a massive disappointment and arguably the worst free agent signing in Yankees history.

Ellsbury played in 520 games from 2014-17. The Oregon native hit an underwhelming .264 with 39 home runs, 198 RBI, and 102 stolen bases. Injuries would sideline Ellsbury for the entire 2018 and 2019 seasons, leading to his release.

While Ellsbury failed to live up to the hype on the field, what he was paid for not playing separates this deal from all others. From 2018-21, the former Gold Glover earned a whopping $68,428,571 for exactly ZERO games played. I’d say that’s worthy of the number-one spot.