Big contracts carry sky-high expectations, yet not every deal delivers. The Yankees have faced staggering setbacks with some of their biggest signings. Injury woes, high-pressure meltdowns, and misjudged potential turned a few marquee names into cautionary tales. Here are ten contracts highlighting the cost of ambition when things go off track.
Jacoby Ellsbury
Speed and star power lured the Yankees into signing Jacoby Ellsbury in 2014 for a staggering $153 million over seven years. Ellsbury’s production peaked early, but persistent injuries sidelined the center fielder for 2018 and 2019. The Yankees paid over $68 million for zero on-field appearances during his final seasons, making this deal a cautionary tale.
Carl Pavano
The hype around Carl Pavano’s postseason dominance in 2004 pushed the Yankees to offer a $39.95 million deal for four years. Unfortunately, a series of bizarre injuries, including a car accident, limited Pavano’s career in pinstripes to just 145 innings. Critics often call this deal a masterclass in buyer’s remorse.
Kei Igawa
Kei Igawa was a high-risk bet that backfired spectacularly. The Yankees invested $46 million between a posting fee and a contract, but Igawa’s 16-game MLB stint left much to be desired. Spending most of the deal in the minors, Igawa symbolizes the pitfalls of scouting miscalculations on the global stage.
A.J. Burnett
In 2009, A.J. Burnett signed for $82.5 million and delivered a solid first year, even securing a World Series victory. By 2011, however, Burnett’s control issues had ballooned, with an AL-high 25 wild pitches. The Yankees had to eat $20 million to offload the pitcher, underscoring how fleeting success can cost dearly.
Jaret Wright
Few contracts have aged as poorly as Jaret Wright’s three-year, $21 million deal in 2005. Signed after a fluke season with the Braves, Wright floundered with a 4.99 ERA and chronic shoulder issues. The pitcher’s brief Yankees career ended with a trade that fans still remember as a financial misstep.
Hideki Irabu
Dubbed “The Fat Toad” by George Steinbrenner, Hideki Irabu’s Yankees tenure (1997–1999) was as rocky as his $12.8 million contract. Despite flashes of brilliance, including a 13-win season, inconsistency and lack of discipline left fans frustrated. This saga further highlighted the pressure of performing under New York’s bright lights.
Ed Whitson
A five-year, $4.4 million deal in 1985 quickly soured when Ed Whitson clashed with teammates and faltered in high-pressure games. It was a road ERA of 2.65 that contrasted sharply with a 6.23 ERA at Yankee Stadium. Unable to handle the Bronx spotlight, Whitson’s failure remains a study in mental preparedness.
Kenny Rogers
Left-hander Kenny Rogers signed for $20 million in 1996 but faltered in the Yankees’ postseason runs. Rogers’ performance, including a 14.14 ERA in the 1996 ALDS, drew sharp criticism. Rogers thrived elsewhere, but the New York stint epitomizes how pressure can derail even seasoned veterans.
Jose Contreras
Jose Contreras joined the Yankees in 2003 after a fierce bidding battle but never found consistency. A $32 million deal brought flashes of brilliance. This included a 17-strikeout game, but also frequent meltdowns. Traded midseason in 2004, Contreras blossomed elsewhere, proving timing is everything in player management.
Alex Rodriguez
Few contracts have sparked as much debate as Alex Rodriguez’s $275 million, 10-year deal in 2007. While Rodriguez’s bat powered the Yankees to a 2009 championship, scandals, injuries, and declining performance turned him into a polarizing figure. His suspension for PED use only deepened the financial and reputational fallout.
