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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 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.

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15 Nick Johnson - 1 year, $5.5 million

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Throwing away $5.5 million on a bad one-year contract isn’t a terrible thing, even if the player only hit .167 with a .306 slugging percentage. But the fact that Nick Johnson only managed 98 plate appearances in 24 games in 2010 made it a complete waste. Brought back mostly for his ability to hit home runs, the Yankees should instead have focused on his ability to hit the disabled list, as he previously missed all of 2007 and most of 2008 with injuries, before a healthy 2009. Managing only two homers for the Yankees, they essentially cost the team $2.75 million each.

14 Ed Whitson - 5 years, $4.4 Million

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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.

Whitson also received hate mail and threats toward his wife and daughter, whom he barred from attending games because of it. The agony finally ended when Whitson was sent back to San Diego in July of 1986.

13 Pedro Feliciano - 2 years, $8 Million

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Even though the Yankees only had to pay former Mets reliever Pedro Feliciano $8 million over two years, it was a total loss considering the amount of time he played for them. A shoulder injury delayed the start of his 2011 season, and he was eventually shut down for the entire year. Feliciano then had offseason surgery on his shoulder, which caused him to miss most of 2012 as well. He ended the season without getting called up, despite completing his minor league rehab assignment. In the end, Feliciano was paid $8 million without ever throwing a single pitch for the team.

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

AP Photo/John Froschauer
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When the Yankees acquired sure-fire Hall-of-Famer Randy Johnson from the Arizona Diamondbacks in 2005 (for Javier Vázquez, Brad Halsey, Dioner Navarro, and $9 million), the Big Unit was coming off an outstanding 16-win season that included a perfect game, and he responded by putting up 17 wins with a 3.79 ERA and 211 strikeouts with his new team. Having already negotiated a two-year extension with Johnson, the Yankees were hopeful for another strong performance in 2006, but only received a 5.00 ERA for the season, and in Game 3 of the ALDS, he coughed up an embarrassing five runs in 5-⅔ innings. All in all, the Yankees blew a whopping $41 million during his short tenure, and would have hit $57 million if it weren’t for a 2007 trade back to the D-Backs.

11 Kevin Youkilis - 1 year, $12 million

AP Photo/Matt Slocum

Even with some nagging injuries, third baseman Kevin Youkilis still played in at least 100 games in each of his 2006-12 seasons with the Red Sox (and the White Sox for half of 2012), hitting .287 with a .388 on-base percentage for Boston. He signed a one-year, $12 million contract with the Yankees for 2013, but only managed a .219 average and .305 OBP in an injury-shortened season with his new team. In fact, with only a shockingly-low 28 games played for New York, the Yankees essentially paid him almost a half-a-million dollars per game.

10 Roger Clemens - >1 year, $18.7 million

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With the Yankees looking for an additional reliable starter early in 2007, Roger Clemens announced his triumphant return to the Bronx during a surprise, mid-game appearance in the Yankee Stadium owner’s box on May 6. Getting another year of Clemens on a $28 million prorated contract (totaling about $18.7 million in the end) is worth it in theory, but not when he only managed a 4.18 era and a career-low 6.2 Ks per 9 innings in 17 starts. That equates to about $10,000 per pitch!

9 Kenny Rogers - 4 years, $20 million

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Coming off a 17-7, 3.38 ERA season with the Rangers in 1995, the Yankees signed starter Kenny Rogers to a four-year, $20 million contract. He responded by posting his second-worst ERA in eight seasons in 1996, and his worst ever in 1997, a 5.65 with a 6-7 record. These numbers were only made worse by the fact that Rogers was allegedly one of the most difficult players Joe Torre ever managed, constantly complaining and clashing with both teammates and members of the press. He was eventually sent to Oakland with cash just to put an end to his turbulent tenure in the Bronx.

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8 Steve Karsay - 4 years, $22 million

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An effective and dependable reliever with the Cleveland Indians and Atlanta Braves, Steve Karsay was rewarded with a generous four-year, $22 million contract with the Yankees in 2001. He delivered in his first season, posting a 3.26 ERA in 78 games as both a set-up man and closer, but shoulder surgery cost him 2003 and most of 2004 as well. After giving up four runs in his first six games of 2005, Karsay was designated for assignment. The best part about his time with the Yankees? When he was sent down, the team called up Robinson Cano.

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

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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.

Although he had moments of brilliance in pinstripes - including six innings of one-run ball in the 2009 ALDS, an immaculate nine-pitch inning, and striking out four batters in another - his name will forever be synonymous with frustration and disappointment for Yankee fans.

6 Jaret Wright - 3 years, $21 million

The Detroit News / Steve Perez
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Considering the fact that Jaret Wright only pitched a single good season (15-8, 3.28 ERA for Atlanta in 2004) in his seven-year MLB career prior to the Yankees inking him in December of 2004, it came as no surprise that he put up a 4.99 ERA and a 1.60 WHIP in only 40 total starts. The only surprise was the fact that New York thought it was a good idea to sign him to a three-year, $21 million contract in the first place. He ended up getting traded prior to his third year, with the Orioles paying less than half of his 2007 salary.

5 Javier Vázquez - 1 year, $11.5 million

AP Photo/Kathy Willens

When the Yankees signed Javier Vázquez prior to the 2004 season, he answered by posting a 4.91 ERA (his worst in five years) capped by surrendering three runs and walking five batters in two innings of a key ALCS Game 7 loss against the Red Sox. He was traded three months later with three years and $34.5 million left on his contract. Then, for some reason, Vázquez was acquired by the Yanks again prior to 2010, and he responded with an even worse 10-10 record and a 5.32 ERA capped by hitting three batters in a row in his final game. Oddly, Vazquez was actually considered one of the best starters in baseball before both Bombers stints.

4 José Contreras - 4 years, $32 million

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José Contreras was a huge star in 2002 when he defected from Cuba and signed a four-year, $32 million contract with the Yankees. Although he posted a 3.30 ERA in his first season, he was inconsistent, moving in and out of the bullpen and back and forth from the minors. He started 31 games the next year, but only posted a 5.50 ERA, and was traded to the White Sox (along with $3 million) for Esteban Loaiza near the end of the season. Just prior to the trade, Contreras had a stretch of two games where coughed up 15 runs in 12 innings.

3 Alex Rodriguez - 10 years, $275 million

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When the Texas Rangers traded Alex Rodriguez to the Yankees after 2003, it was a pretty good deal for New York, considering Texas paid $67 million of the $197 million still owed to A-Rod and he rewarded his new team with four outstanding seasons and two MVP Awards. However, Rodriguez opted out of the contract at the end of 2007, only to re-sign with the Yanks for an even larger, 10-year, $275 million contract. As expected for a contract that would take an infielder into his age-42 season, A-Rod’s performance declined, his injuries became most frequent, and his name was also forever sullied by lies, steroid admissions, and a year-long suspension. Even now, Rodriguez still has two full years left on his contract.

2 Carl Pavano - 4 years, $39.95 million

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When the Yankees signed Carl Pavano before the 2005 season, he had just finished an 18-8, 3.00 ERA year with the Florida Marlins, and started at least 31 games in each of his previous three years. This begs the question, what was the most disappointing part of his four-year, $39.95 million stint with the Yankees: the fact that he only pitched to a 5.00 ERA and a 1.45 WHIP, the fact that injuries limited him to only 26 starts, or the fact that he was injured in a car accident and completely withheld the information from the Yankees? It doesn’t matter, as it all adds up to a laughably-regrettable contract for an extremely disappointing athlete and teammate.

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

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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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