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…

More Articles About the Worst of the Yankees:

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.