5 worst contracts in modern New York Yankees history

4. DJ LeMahieu

One of my favorite players! The Yankees’ Team MVP from 2019-2020! Someone who was clearly hurt by the disappearance of the rocket balls in 2021, and can theoretically remain a valuable player as he ages!

Still, it’s hard not to put a player on this list who signed a six-year, $90 million contract, but will apparently be converted to a roving utility infielder and lose his starting job in Year 2.

Now that Rob Manfred has admitted he’s been using (at least!) two different baseballs the past several years in both showcase events and “boring” games (which the Yankees rarely play), LeMahieu’s 2021 regression is a bit more explainable. Factor in the core muscle surgery he had to repair a sports hernia that knocked him out of the Wild Card Game, and you’ve got one reason for hope that things can change for the duration of the deal, even if Manfred doesn’t touch the baseballs ever again.

That said, LeMahieu, now 33, is coming off a season where he ranked 12th percentile in barrel percentage and in the 32nd percentile in expected slugging. He still hit the ball moderately hard, but he hit it on the ground far too often, resulting in an overload of double plays even when he was at his theoretical best.

You can’t rule out his contributions moving forward, but when Hal Steinbrenner points to LeMahieu’s deal as a retrospective reason he stayed out of the shortstop market this offseason, all while picking him up and moving him all around the diamond (first base?) in a desperate attempt to justify the investment, you can’t help but trend the contract towards the “mistake” column.

3. Kei Igawa

Maybe the news cycle just didn’t dig as deeply in those pre-Twitter days? Maybe we just didn’t have access to enough information, as fans?

But when Kei Igawa came over from the Hanshin Tigers at the tail end of the 2006 season, accepting a $26,000,194 (the last three numbers representing his strikeout total) bid and a five-year, $20 million contract, he was thought of as not quite Hideo Nomo, but still someone who could make a meaningful and immediate contribution to the back end of a big-league rotation.

Did we not know his elite-level performance had declined significantly in 2004 and 2005 overseas? He posted ERAs of 3.73 and 3.86 after winning the MVP and Cy Young equivalent back in 2003. Hell, he’d even been exiled to the Japanese minor leagues for a stretch in ’05, which we’re pretty sure would never happen to Mike Trout if he had a tough few weeks.

When Igawa left Japan, he’d been the target of significant fan criticism, and unfortunately brought his regression with him to the Yankees. In late April of 2007, he broke out, replacing an injured Jeff Karstens with six innings of brilliant relief against the Red Sox in a 3-1 win.

That was as good as it got. He finished 2007 with a 6.25 ERA in 12 starts, then “finished” 2008 with a 13.50 ERA in just two short outings (13 hits allowed in four innings).

Yes, Igawa was mostly paid to pitch and live in Scranton until his Yankees contract ran out — though he actually reportedly blocked two Brian Cashman attempts to sell him back to Japan, so that was partially his choice.

What a life.

2. Carl Pavano

Hey, happy 46th birthday a few days ago, Carl Pavano! You were the absolute worst variety of Yankee signing.

Yes, even more insufferable than the No. 1 spot on our list.

After all, you’ve got to love a guy who takes big money, spends the entirety of his contract injured, then immediately gains a second wind after joining another team, vowing (and exacting!) revenge on a team that did nothing wrong.

Seriously, how can you go scorched earth on the Yankees for three years of … having to deal with you being a staggering disappointment? It’s the kind of thing that seems to happen to this team all the time. Former Yankees who struggled in pinstripes saving their very best for the team that “wronged” them by twiddling their thumbs and not receiving results.

Carl Pavano, a former Red Sox top prospect and Connecticut native, turned down larger offers from Boston, Detroit and Cincy to sign a four-year, $39.95 million contract with the Yankees after the 2004 season. The post-2004 “we lost badly!” pitching splurge doesn’t get nearly the hatred of the 2014 spending spree, but it was stunningly pointless in retrospect.

The move made sense! Pavano, just 29, was coming off a special season in Florida where he threw 222.1 innings, kept the ball on the ground, and finished sixth in the Cy Young voting (18-8, 3.00). He began 2005 with a 4–2 record and a 3.69 in 10 starts before succumbing to shoulder pain, throwing off the trajectory of his campaign.

Then came 2006, a disaster unlike any other. He missed the start of the year with a literal bruised ass, suffering a buttocks injury in the spring. He then proceeded not to pitch at all at the MLB level, making a few rehab starts before breaking his ribs in a mid-summer car accident and then not telling the Yankees about it until the day before he was supposed to be activated. Again, does this sound like someone who was “wronged”? In 2007, he returned, struggled, and had Tommy John surgery, returning to make seven starts with a 5.77 ERA in 2008.

In 2009, he left … and threw 199.1 innings immediately, split between Cleveland and Minnesota, where he met the Yankees in Game 3 of the ALDS! Luckily, this story has a happy ending. As red as Pavano’s ass still was, for whatever reason, he carried a shutout into the seventh inning of that game, at which point Alex Rodriguez hit a baseball so hard off him to right-center that it unraveled and turned to dust when it struck the baggie at the Metrodome. He also gave up a dinger to Jorge Posada minutes later, officially taking the L in the game and the series.

In 2010, he tried again. After a dominant season (17-11, 3.75 ERA, COME ON HOW IS THAT POSSIBLE?!), Pavano again lost Game 2 of the ALDS this time, giving up a tie-breaking homer to Lance Berkman.

Sorry, man. Maybe don’t try to cover up a car accident next time? Would love to hear Pavano’s side of the story. As of now, I’ll never get it.

1. Jacoby Ellsbury

When you get rubbed out by the mafia years before your contract is supposed to expire, only to resurface years later as part of a Red Sox troll, you know the deal probably went south at some point.

Hey, at least we knew where Pavano was … well, after 2006, at least. And at least Pavano wasn’t signed for seven years!

Boston’s ultimate revenge on the Bombers came when New York chose to sign Jacoby Ellsbury to a seven-year, $153 million contract after the 2013 season. They watched the insufferable “Get Beard” team win a third Red Sox ring in less than a decade and decided any price would be worth it to steal that team’s heart and soul, Johnny Damon-style.

They were incorrect.

People forget Ellsbury’s 2014 season was actually good. People forget that because 2014 was a completely forgettable season in Yankees history, and the Ellsbury expectations were much higher at the time (probably wrongfully so, but still) than 16 homers, 70 RBI and a 111 OPS+.

After that, though, things went off the rails. Ellsbury played in 111, 148, and 112 games in the next three seasons, posting OPS+ marks under 100 and typically looking more like a replacement player than an electric superstar. The short porch at Yankee Stadium didn’t help him at all; the power was gone (seven, nine, and seven home runs). Nobody was expecting a replica of 2011 (32 bombs!), but the low-20s at our tiny ballpark would’ve been nice.

Entering 2018, the Yankees clearly had no intention of using him if they didn’t have to, and he missed the entirety of the next two seasons with a hip labrum tear, plantar fasciitis, and a shoulder issue. At least, that’s what we were told.

When the Yankees released him, they tried to sneak out of the remainder of his contract by claiming he’d received unauthorized medical care, an objectively scummy move. The MLBPA agreed, filing a grievance and getting Ellsbury paid (and nearly costing the Yankees a draft pick in the process).

Ellsbury was technically passable on the field for the Bombers, but when his deal went south, the Yankees couldn’t take the embarrassment, and the ugliness of this deal — most of which falls on Yankee management — makes it a clear No. 1.

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