It seemed like Cole was ready to force the Yankees’ hand until a last-minute change of heart.

World Series – Los Angeles Dodgers v New York Yankees – Game 5 / Sarah Stier/GettyImages

Scott Boras is not a man accustomed to losing a game of chicken. You don’t become MLB’s preeminent power broker by not knowing exactly how much leverage you have and exactly how and when to maximize it, after all. So from the moment the New York Yankees’ season ended in heartbreaking fashion in Game 5 of the World Series, it seemed all but assured that one of Boras’ biggest clients, ace Gerrit Cole, would have GM Brian Cashman over a barrel.

The nine-year, $324 million contract Cole signed with New York in the winter of 2019 came with a player opt-out at the end of the 2024 season, allowing the righty to become a free agent unless the the Yankees added another year and $36 million onto the original deal. Given the going rate for premium starting pitching these days, as well as just how thin New York’s starting rotation would be if he walked, opting out seemed like the smart play for Cole to maximize his value. And sure enough, Cole did just that on Sunday afternoon, giving the Yankees precious little time to come to an agreement on a new deal — or risk losing the anchor of their pitching staff for nothing.

But then something virtually unprecedented happened: Despite seeming to hold all the cards, Boras blinked, and it was instead Cashman who got his way.

Scott Boras, Gerrit Cole blink first in staredown with Yankees GM Brian Cashman

Late Sunday evening, word broke that actually Cole wouldn’t be opting out after all. And not because he and the Yankees had reached an agreement on a new extension; on the contrary, Cole would continue to play out the contract he initially signed five years ago, a stunning reversal.

While we may never know exactly what went down between Cole and the Yankees, it sure seems like Cashman did what anyone hardly ever does to Boras: He called the superagent’s bluff. Cole remains a very good pitcher, but he also just turned 34, and there some red flags in his profile — from the elbow injury he dealt with this season to his declining velocity and whiff rate. Those red flags are why Cashman was reportedly “uncomfortable” tacking another year onto the end of Cole’s deal:

It’s also why he was apparently not uncomfortable letting Cole test the market: Any team signing Cole to a deal that would carry him toward his 40th birthday would have reason to be concerned, and Cashman was willing to bet that the righty’s market in free agency wouldn’t be as rosy as the four years and $144 million he had remaining on his current deal. It seems like that bet was correct, because it took Cole and Boras just a few hours to change their minds; if a contending team was willing to beat the Yankees’ price, it stands to reason that he would be a free agent right now.

You have to tip your cap to Cashman here. After the way his team’s season ended, he could scarcely afford the PR hit of losing his best pitcher in a game of chicken. But he knew that Cole wasn’t likely to find a better competitive and financial situation than the one he currently has in New York, and he managed not to let fear cloud his judgment and let Boras roll him over. The first box on the Yankees’ offseason to-do list has been checked, but the job will only get harder from here.