The New York Yankees are known for shelling out big-money contracts, especially during George Steinbrenner’s era. They were never afraid of throwing money at free agents to fill holes. However, there have been quite a few deals that never worked out. Here are the 10 worst free-agent contracts in New York Yankees history.
10. Roger Clemens: 1-year, $18.7 million
Roger Clemens’ first stint in Yankees pinstripes went swimmingly. From 1999-2003, he captured the 2001 AL Cy Young Award, was a two-time All-Star, and won two World Series championships. However, his second time in the Bronx didn’t go quite as well. In 2007, he signed a one-year, $18.7 million contract in May of that season. He made 18 starts, going 6-6 with a 4.18 ERA. He was unable to be the “Rocket” of old. It also turned out to be Clemens’ last time in the majors.
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9. Alex Rodriguez: 10 years, $275 million
Alex Rodriguez might have been one of the greatest players of his generation, but he was also one of the Yankees’ biggest headaches. He signed a 10-year, $275-million deal going into the 2008 season after opting out of his original contract. From 2008 to 2016, Rodriguez was limited due to injuries and was suspended for the entire 2014 season for PED use. The Yankees cut Rodriguez at the end of the 2016 season despite having another year left on his contract.
8. Brian McCann: 5 years, $85 million
Going into the 2014 season, the Yankees thought they had one of the best catchers in baseball in Brian McCann. He came over from the Atlanta Braves after seven All-Star seasons. The Yankees never saw that kind of productivity. In three seasons, he had a 99 OPS+ and just a 5.7 WAR. New York ended up trading McCann to the Houston Astros in Year 4 of the deal.
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7. Kevin Youkilis: 1-year, $12 million
It was a weird sight seeing Boston Red Sox favorite Kevin Youkilis in a Yankees jersey, but that’s exactly what happened in 2013 — his last year in the majors. Youkilis signed a one-year, $12 million deal, and New York pretty much lit their money on fire. Youkilis played in just 28 games, hitting two home runs and accumulating a negative 0.4 WAR.
6. Jose Contreras: 4 years, $32 million
The Yankees thought they were getting the next big thing when they signed Jose Contreras to a four-year, $32 million contract ahead of the 2003 season after he defected from Cuba. However, it wasn’t meant to be. Contreras lasted less than two seasons in the Bronx, as the Yankees traded him to the Chicago White Sox in 2004. He went 15-7 with a 4.64 ERA in New York.
5. A.J. Burnett: 5 years, $82.5 million
A.J. Burnett wasn’t the ace the Yankees envisioned when they signed him to a five-year, $82.5 million deal going into the 2009 season. Over three seasons with New York, Burnett went 34-35 with a 4.79 ERA and mediocre 92 ERA+. He was eventually traded to the Pittsburgh Pirates ahead of the fourth year of his deal in 2012.
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4. Carl Pavano: 4 years, $39.95 million
The Yankees would like to forget this disaster of a signing. New York gave Pavano a four-year, $39.95-million contract going into the 2005 season. Over four seasons with the Yankees, Pavano made only 26 starts, going 9-8 with a 5.00 ERA and 86 ERA+. To make matters worse, in 2006, when he missed the entire season, he hid from the Yankees that he was involved in a car accident and suffered two broken ribs.
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3. Hideki Irabu: 4 years, $12.8 million
Hideki Irabu is a sad tale. He was a pitching sensation in Japan but was never able to find that success in the United States. The Yankees gave Irabu a four-year, $12.8-million contract in 1997, but he was unable to live up to the hype. He wasn’t well-liked in the front office or the clubhouse during his tenure. After three seasons, the Yankees traded him to the Montreal Expos. Irabu last pitched in the big leagues in 2002. He died by suicide at the age of 42 in July 2011.
2. Kei Igawa: 5 years, $20 million
The Yankees tried their luck with another top Japanese pitching star that didn’t pan out. Ahead of the 2007 season, the Yankees gave Igawa a five-year, $20-million deal. They also had to shell out $26 million for the posting fee. The signing was an unmitigated disaster. Igawa made just 13 starts over two seasons, with a 6.66 ERA and 2-4 record. He finished out the rest of his contract pitching in the Yankees’ minor league system.
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1. Jacoby Ellsbury: 7 years, $153 million
Don’t ever mention Ellsbury’s name around Yankees fans. The Yankees thought they had found their center fielder in 2014 after he came over from the Boston Red Sox; instead, they got a $153-million migraine. Ellsbury played in only 520 out of 972 games due to injury — missing all of 2018 and 2019. The Yankees released him in November 2019, and he hasn’t played in the majors since.