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.

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.