Gerrit Cole’s Contract Situation With Yankees Is Incredibly Bizarre

Gerrit Cole did his best to keep the New York Yankees in the World Series, turning in two excellent starts in Game 1 and Game 5. Well, outside of forgetting to cover first base in the pivotal fifth inning of Game 5. 

The postseason performance reinforced the fact that Cole is one of the few true “aces” left in Major League Baseball. Able to turn lineups over three times, command his pitches, and work deep into games with elite stuff. For the Yankees, hoping to run it back for 2025 and finally win another championship, he’s as valuable as it gets.

Cole, a day after the end of the World Series, decided to test that value. 

Written into the contract that started in 2020 was the ability to opt out of the remainder of his deal after the 2024 season. Instead of four years and $144 million, the Yankees would have to add another year and $36 million in guarantees, otherwise Cole would become a free agent. He opted out.

Sounds pretty clear-cut, right? Either New York would agree to have Cole for the next five years at $180 million, or he’d instantly become one of the top pitchers on the open market. Except…neither of those things happened. 

NEW YORK, NEW YORK – OCTOBER 30:  Mookie Betts #50 of the Los Angeles Dodgers safely reaches first base on a soft grounder as Gerrit Cole #45 of the New York Yankees fails to cover first base on a miscommunication with Anthony Rizzo #48 during the fifth inning of Game Five of the 2024 World Series against the Los Angeles Dodgers at Yankee Stadium on October 30, 2024 in the Bronx borough of New York City. (Photo by Al Bello/Getty Images)

Gerrit Cole, Yankees, Have Contract Standoff

Initially, it was reported that the Yankees would have until midnight eastern time on Sunday to decide on the additional year. Then, more reports surfaced that the deadline had been pushed back to Monday afternoon.

Monday afternoon came and went and…nothing happened.

Jon Heyman, among others, posted on X on Monday afternoon that Cole and the Yankees had “agreed to stay together.” Then he added more context, saying that the two sides had agreed to essentially continue on with the existing, four years and $144 million remaining.

What now?

The simplest explanation here is that Cole, and his agent Scott Boras, initially thought they could force the Yankees’ hand by opting out. Give us the additional year and guaranteed money, or we’ll test the open market. Brian Cashman and the organization apparently looked at the market, Cole’s age, arm injury and declining velocity and said “thanks, but no thanks.”

And Cole, not actually wanting to be a free agent and go elsewhere, said, “ok fine, I’ll just stay with the deal I just opted out of.”

What a bizarre situation; Cole had every right to become a free agent after the Yankees declined to pick up his option, and just…didn’t. How this played out all but guarantees that it was a player-led decision to stay in New York, but Boras rarely, if ever, turns down the opportunity to start a bidding war. It’s debatable whether Cole could get five years and $180 million from another team at age-34. 

But it isn’t debatable that he clearly wanted to stay in New York. And so he is. Weird.