Yankees worst free agent contracts ever handed out

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(Photo by Rich Schultz/Getty Images) Yankees /

When the Yankees released Jacoby Ellsbury on Nov 21 — still owing him $26 million over the next two seasons, he joined a list of tumultuous mistakes the Yankees have made in free agency.

With how much cash the Yankees have, they can push the envelope on a deal harder than any other organization. But like a teenage girl splurging at Kendra Scott, there is bound to be a couple of cases of buyers remorse among the successful purchases.

There are some curious cases when it comes to Yankee contracts. Obvious ones come to mind, such as A.J. Burnett. Yes, his 5-year, $82.5 million contract was hefty, and he had an overall shaky time in the Bronx.

But when he was truly needed, he would rise to the occasion, just like his brilliant one-run game in Game 2 of the 2009 World Series. Compared to the others, at least Burnett helped secure some silverware. And when Burnett got going, his knuckle-curve was near untouchable.

However, it’s cases like Burnett that are swept under the rug and forgotten, and wisely so, but they serve as mistakes to learn from, especially for the GMs. So let’s unearth these miscues and take a look at the worst free-agent contracts in Yankees history.

Roger Clemens

When Clemens addressed the Yankee crowd up from the comforts of George Steinbrenner’s box in May of 2007, fans knew Clemens’ second term would soon begin. He was coming off yet another abnormally brilliant year for a guy his age (44-years-old), pitching to a 7-6 record with a sparkling 2.30 ERA with a 1.04 WHIP in his last year with the Astros.

This did, however, come with the fact that he didn’t even play the full season and averaged just under six innings per start. However, the armor was beginning to rust a bit. But the Yankee brass felt he would bolster a pitching core littered with free-agent mistakes I’ll go over later.

Clemens was given a pricey 1-year, $18.7 million contract with all sorts of special treatment, such as a family clause that stated he could skip road trips if he weren’t scheduled to pitch and allowed him to leave the team in between starts to be with his family.

He had an otherwise mediocre year, posting a 6-6 record with a 4.18 ERA in 17 starts. He was at least able to earn his 350th win, cementing him as one of only three pitchers to solely pitch in the live-ball era and reach 350 victories. But besides that accolade, it was a very forgettable end to the Rocket’s career.

Carl Pavano

One other pitcher who was on that 2007 Yankees roster was Carl Pavano. When the Yanks signed Pavano to a 4-year, $39.95 million contract after the 2004 season, they were expecting an ace who was entering his prime and ready to dominate.

After all, he had a stellar year with the Marlins, where he posted an 18-8 record with a 3.00 ERA.

He even pitched well in the Marlins’ 2003 World Series-winning season, only allowing one run in eight innings vs. the Yankees in Game 4.

Well, he was anything but stellar during his tenure in the Bronx. In four years, he compiled a 14-12 record with an ERA of 5.10 to go along with countless injuries.

The timing of these injuries was almost comical. Pavano started 2006 on the DL with a bruised glute. Seriously. Then he broke a couple of ribs in a car accident but refused to tell the team until the day the Yankees were going to take him off the DL.

Because of this, Mike Mussina flat out said that Pavano had much to prove to pitch for New York. When all was said and done (or not done), Pavano unceremoniously earned the nickname “American Idle” in his final year with the Yankees for his distinct lack of action.

Pavano added salt to the wound by having some decent seasons with the Minnesota Twins after he left the Bronx — like posting a 17-11 record with an ERA of 3.75 in 2010.

Kei Igawa

Yet another pitcher on that 2007 roster. Kei Igawa was another name in a long list of former Japanese All-Stars trying their hand on American shores. His signing in 2006 was a knee-jerk reaction to Boston outbidding and claiming coveted Seibu Lions pitcher Daisuke Matsuzaka.

Igawa was dominant in 2003 (20–5 record, 2.80 ERA) for his Hanshin Tigers, but his play fell off consequently in 2004 and 2005. He was even sent down to the minors for a brief period and was heckled by fans.

He had strikeout ability, but control issues plagued him. Despite the warning signs, the Yankees signed Igawa to a 5-year, $20 million deal (not including the $26 million posting fee). Igawa would go on to appear in just 16 games for the Yankees, posting a subpar 2-4 record with an ERA of 6.66 (spooky).

Igawa was thus cast to minor league purgatory, becoming a player earning about 130 times the average farmhand. Igawa even set the Scranton-Wilkes/Barre record for most wins.

When one dives a bit more, Igawa becomes a curious and even sympathetic case. Ian Pennington of the New York Times detailed his journey and what brought Igawa to the minors. Igawa always had the work ethic and willingness to adapt, but he was simply outmatched in a land and environment where he was unfamiliar.

But at the end of the day, he will be remembered by what Brian Cashman admitted. “It was a disaster. We failed.” Hey, at least Igawa had a really high rating in MLB ’07 the Show, higher than Daisuke, even.

Mandatory Credit: Ezra O. Shaw /Allsport /

Hideki Irabu

Igawa wasn’t the only failed Japanese experiment for the Yankees. Hideki Irabu was a mainstay in the Japanese League before the Padres expressed interest in him in 1997, buying his contract from the Chiba Lotte Marines.

He, however, only wanted to pitch for the Yankees, so the club made a trade for him. Irabu was hyped beyond belief as one of the first Japanese pitchers in MLB and as a potential ace for the Yanks, but he flamed out rapidly.

Over two seasons, Irabu posted a 29-20 record and 4.80 ERA. He had a few decent months but proved to be a wildly inconsistent pitcher. His weight and work ethic were brought up often, as George Steinbrenner even commented that Irabu was a “fat p***y toad” after he failed to cover first base in a spring training game.

Irabu was then traded to the Expos in 1999 and experienced a meager career after that. He couldn’t cut it as a closer for the Rangers and a Japanese League revival sputtered. Many remember him solely as a joke from Seinfeld, where George Costanza’s dad questions Steinbrenner — and how he can give $12 million for Irabu.

It wasn’t the first time Costanza chastised Steinbrenner, as he interrogated him for trading Jay Buhner in Season 7. Sadly, Irabu committed suicide in 2011. Ben Reiter’s Sports Illustrated article detailing Irabu’s troubled life is a great read.

Jacoby Ellsbury

And that brings us to the modern-day, where the Yankees recently released Jacoby Ellsbury after giving him a ludicrous 7-year, $153 million contract in 2014. Ellsbury was known for his plus speed and power combo, but surely he wasn’t expected to maintain that in his later 30s?

Despite that, the Yankee brass handed him that contract, praying for another Johnny Damon. Well, he failed to live up to that billing spectacularly. Ailing health and overall poor center field play doomed him to the bench for the likes of Aaron Hicks.

Ellsbury hadn’t played for the Yankees since Sept 30, 2017, due to a laundry list of ailments. He suffered concussions, a torn labrum in his left hip, plantar fasciitis, and numerous minor shoulder issues.

He was forever present in the medical reports but not in the stat sheet. Ellsbury started becoming a running joke amongst Yankee fans, often saying he’ll be back better than ever (sarcasm).

And when he was released, many popped off. The sage isn’t even over yet, as the Yankees plan on exempting the $26 million they owe him, due to Ellsbury receiving unauthorized medical care from a doctor in Atlanta that the club didn’t approve.

When all is said and done, Ellsbury posted a mediocre .264 batting average with 39 homers and 198 RBIs in six seasons with the Yankees. He will be the gold standard for bad Yankee contracts.

Spin Zone Contracts

Such a strange year was 2013. The Yanks missed the playoffs, it was their worst finish since 1992, and they had Kevin Youkilis under contract. That’s right, a player embedded into Red Sox lore spent time in pinstripes (shocker).

Youkilis’ contract wasn’t horrible by any means; it was a relatively fair 1-year, $12 million deal. But he was just flat outdone as a major league player. He batted an abysmal .219 with two homers and eight RBIs in 105 at-bats.