What…happened here, exactly?

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

Ok, who blew it in the Gerrit Cole opt-out debacle? Scott Boras? The Yankees? Absolutely no one? Because, if I didn’t know any better, I would say this looks like the second time in a week that Cole forgot to cover the bases.

Following Cole opting out of his contract on Saturday afternoon — as largely anticipated, given the Yankees’ ability to merely tack on an additional year — the first hint that something was up came on Sunday. As fans eagerly anticipated a decision, Mark Feinsand noted that the deadline for a finalized contract was suddenly Monday.

Had that been the case all along? Had we simply gotten it wrong? Or had something shifted, mid-gaslight?

As it turned out, Cole and the Yankees spent Monday “making positive steps toward a return to pinstripes,” but not in a creative way that helped them bank financial flexibility for 2025. Instead, the Yankees clearly told Cole they weren’t interested in adding the fifth year to the back end of the deal, and Cole decided later than he should’ve that he preferred to return to New York rather than shop around.

They didn’t negotiate a new deal. They didn’t defer anything at all. They didn’t even really keep extension conversations open, which was hinted at when the news first broke (though technically that’s a future possibility). They just erased 48 hours worth of drama and moved on, which feels like a Boras miscalculation (and a rare show of force from Brian Cashman’s front office).

Brian Cashman reveals Gerrit Cole never wanted to leave, Yankees never wanted to add time to contract

As Cashman noted to the masses gathered at the GM Meetings on Monday evening:

“Cashman said that club decision-makers ‘weren’t necessarily comfortable’ voiding the opt-out by adding a year and $36 million to the deal, which they communicated to Cole and agent Scott Boras.

‘We wanted our player and our ace back, and he certainly didn’t want to go either,’ Cashman said at the GM Meetings in San Antonio, Texas. ‘We had a lot of healthy dialogue about trying to thread the needle and keep it in play. We could always talk further as we move forward about the future’.”

At the time of Cole’s opt out, it felt absurd that the “Yankee Fan Today, Tomorrow, Forever” ace would feel comfortable risking the severing of his relationship with his childhood team on a sour note like Game 5. Surely, the two sides had come to an accord before the trigger was pulled, and a resolution would be swift and would come according to the terms of the initial deal.

Apparently, we can’t be so sure. Cole appeared to be flying relatively blind, but had just as little interest in exploring the market as Cashman did in paying him for his age-38 season. Whose fault is that? And will the Yankees be interacting with this “fault” again later in the offseason?