5 worst contracts in modern New York Yankees history

Everybody wants the New York Yankees to sign every contract until they sign an awful one.

Then it’s all, “Hey, why did you do that?!” Nature of the beast. We get it. No one wants to believe the Yankees have a budget, but unfortunately, they do, and every free agent miscalculation of the past makes them extra skittish about the next decision.

And whew, boy, did they have a lot of miscalculations about the past.

For all the chatter about the Yankees “buying championships” during their golden haze, that strategy was only really executed to perfection once in 2009, when Mark Teixeira, CC Sabathia and AJ Burnett arrived just in time — though, of course, the Core Four and A-Rod were just as important to that title run as any free agent expenditure.

No, for the most part, the Yankees’ post-2000 free agent ventures involve half-measures, attempts to buy low, and absolutely pointless overtures to damaged pitchers and shots in the dark.

When the Yankees sign a few high-priced free agents to supplement their roster, it’s “buying a championship,” but when any other team does it, that’s just baseball. Right-o!

So, as the MLB lockout hopefully comes to a close and the Yankees maybe, possibly, hopefully jump into the Carlos Correa/Trevor Story market, feel free to remind the haters that New York’s braintrust doesn’t do this kind of thing as regularly or as effectively as they probably think we do.

Also, don’t show the haters this catalogued list of all the mistakes this franchise has made along the way. They’d probably enjoy that.

Editors Note: We will not be placing the Giancarlo Stanton contract on this list of worst contracts. Stanton is very good, and all of a sudden, his contract looks like a relative bargain. He’s getting paid Javier Baéz money. Deal with it.

Second Editors Note: No Gerrit Cole, either. Come on, nerds. They had to do it.

There. Now, without further ado…

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5 worst contracts in modern New York Yankees history

5. Jarret Wright

Ah, yes. One of my favorite Yankees pitfalls.

“Oh, whoa, we have the chance to sign the guy who owned us in the 1997 playoffs? Don’t question it, just do it.”

“But, sir, it’s 2004.”

“Sorry, already did it while you were talking.”

Jaret Wright (with just one “T”) was brought up by Cleveland midway through the 1997 season to act as a spark plug and get a scuffling team over the hump, and he pitched fairly well down the stretch, relying mostly on a blazing, upper-90s fastball. He won both his starts against the Yankees in a five-game ALDS (that’s big!), then carried the team to the World Series after all, where he figured prominently, starting Game 7 and leaving with an eventually-blown lead.

The Yankees got their revenge in 1998, battering Wright to a 8.10 ERA in a pair of ALCS outings, and he was never quite the same pitcher after those early years.

Of course, that didn’t stop the Yankees from trying to sign him as a bandage after watching their Andy Pettitte-less pitching staff cough up the 2004 ALCS in Boston!

Wright went 15-8 with a 3.28 ERA for Atlanta in 2004, though he only struck out 159 batters in 186.1 innings pitched. The signs of regression were there in the postseason when Wright got lit up by the Astros (10 earned runs in 9.2 innings), but no matter — the Yanks signed him to a three-year, $21 million deal anyway.

That “third year” was spent with the Baltimore Orioles.

Wright’s first season in the Bronx featured just 13 starts, and none of them were very good (5-5, 6.08 ERA). In fact, his best quality was that his shoulder issues helped spur on the Shawn Chacon/Aaron Small second-half surge.

The next season, Wright “rebounded” with an 11-7 record and 4.49 ERA, along with a pitiful 84 strikeouts in 140.1 innings pitched. He even got a playoff start that year! 2.2 innings pitched, four runs (three earned), and a 10.13 ERA.

A few months later, he was jettisoned to Baltimore in exchange for Chris (Don’t Call Me Zack) Britton. $21 million isn’t that much, but the Yankees would’ve been better off running a pitching machine out there for free.

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.

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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