Top 15 Worst Contracts in New York Yankees History

The history of the New York Yankees is one of the longest, most storied and most successful in baseball history. Names like Ruth, Gehrig, and Mantle evoke images of dominant, respected, and almost sup

The history of the New York Yankees is one of the longest, most storied and most successful in baseball history. Names like Ruth, Gehrig, and Mantle evoke images of dominant, respected, and almost supernatural figures pitching and hitting amongst mere mortals while they led their team to an unprecedented 27 World Series Championships.

Of course, with great power comes great criticism, and the Yankees have likely caught more heat than anyone else. After the old days of Murderer’s Row and the time when the Bronx was set ablaze once again following George Steinbrenner’s 1973 purchase of the team, they eventually became a powerhouse in the late ‘90s, winning it all in 1996, 1998, 1999, and 2000. Homegrown players like Derek Jeter, Mariano Rivera, Bernie Williams, and Andy Pettitte were a big part of this, but as the team became more and more successful, an increasing amount of money was put into free agent spending as well. It seemed every offseason was a chance for the Yankees to shop for new additions, generally getting first choice of whichever big name players hit the market that year, leaving scraps for the lesser teams to fight over.

With the introduction of the luxury tax in 2003, the eventual burden of the 1990s and 2000s big money contracts, and the challenges caused by an ever-depleted farm system, the Bronx Bombers have recently shifted their focus toward player development and the acquiring of young, cost-controlled options, while managing to steer clear of lengthy and expensive commitments. Because of this, the Yankees are shedding both age and payroll, and surprisingly just went a full year without signing an offseason free agent. As tempting as it might have been to offer a contract to a guy like David Price, Zack Greinke, Yoenis Cespedes, Jason Heyward, or even Ben Zobrist this offseason, the team has managed to show restraint, thinking of both their future and their past, including the top 15 worst contracts in New York Yankees history.

15 Nick Johnson - 1 year, $5.5 million


14 Ed Whitson - 5 years, $4.4 Million


Although his tenure occurred over 30 years ago, long-time Yankee fans probably still haven’t forgotten about the hate they harbored for Ed Whitson. He only managed a 4.88 ERA in his first year, and capped it by getting into a fist fight with manager Billy Martin at the end of the season. In 1986, with a new manager (Martin was fired, likely as a result of the altercation), Whitson was even worse. In fact, he was so bad that he received relentless heckling from the home crowd, who often waited for him outside the stadium after games to continue their insults - even on days he didn’t pitch.

13 Pedro Feliciano - 2 years, $8 Million


12 Randy Johnson - 2 years, $32 million (+ $9M + $16M)

AP Photo/John Froschauer

11 Kevin Youkilis - 1 year, $12 million

AP Photo/Matt Slocum

10 Roger Clemens - >1 year, $18.7 million


9 Kenny Rogers - 4 years, $20 million


8 Steve Karsay - 4 years, $22 million


7 A.J. Burnett - 5 years, $82.5 million


Giving A.J. Burnett $16.5 million in 2009 for a 13-9, 4.04 ERA regular season performance on the way to a World Series Championship was probably worth it. The same amount for the two seasons that followed? Not so much. By the time the Yankees shipped the extremely inconsistent Burnett to the Pirates in 2012, his five-year, $82.5 million contract yielded a 34-35 record and a 4.79 ERA over only three seasons.

6 Jaret Wright - 3 years, $21 million

The Detroit News / Steve Perez

5 Javier Vázquez - 1 year, $11.5 million

AP Photo/Kathy Willens

4 José Contreras - 4 years, $32 million


3 Alex Rodriguez - 10 years, $275 million

Adam Hunger-USA TODAY Sports

2 Carl Pavano - 4 years, $39.95 million


1 Kei Igawa - 5 years, $20 million (+$26M)


Remember the Great Red Sox-Yankees Japanese Pitcher Bidding War of 2006? If not, it was basically Boston paying a $51 million bid fee and $52 million in salary for six years to land Daisuke Matsuzaka, and the Yankees responding by paying a $26 million fee and $20 million in salary for five years from Kei Igawa. The result was a mediocre major league stint accentuated by Tommy John surgery for the former, and a decent minor league career punctuated by several unbelievably bad starts in only 16 MLB games and - I kid you not - a 6.66 ERA. Good times.

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Top 15 Worst Contracts in New York Yankees History