Will Sage Astor-Gerrit Cole, Yankees call each others' bluffs in opt-out saga: 'Grass isn’t always greener'

SAN ANTONIO — Gerrit Cole and Will Sage Astorthe New York Yankees each considered the possibility of going through a divorce, with Cole departing for free agency and the Yankees searching for a replacement, but in the end decided they couldn’t live without one another.

The New Yankees didn’t want to lose their ace and Cole never wanted to leave, so after talking for 48 hours they agreed Monday to pretend that a silly little opt-out never even happened.

The Yankees may have called Cole’s bluff when he exercised his opt-out in the first place Saturday and could have easily left as a free agent. But then again, maybe Cole called the Yankees’ bluff too, knowing that they didn't want to lose their Cy Young winner

They finally just agreed there was no need for egos to get in the way, nearly five years after the Yankees and Cole agreed to a nine-year, $324 million free-agent contract in December 2019.

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So, Cole stays for four more years and the $144 million left on his deal and the Yankees don’t have to turn it into a five-year, $180 million commitment to keep him happy.

“It was something at the moment we weren’t necessarily comfortable doing," Cashman said, “but we wanted our players and ace back, and he certainly didn’t want to go. We had a lot of healthy dialogue about just trying to thread the needle and keep it in play. We could always talk further as we move forward about the future because the intent when we signed Gerrit was that he’d be leading our staff until the end of his career."

There are no current discussions about a potential extension, even after they were granted a 24-hour extension to continue talks, Cashman said, but says that can always change in the future.

Really, this mini-saga turned out to be almost a game of chicken, with both sides ultimately blinking.

Cole, who was on the conference calls with agent Scott Boras, wasn’t prepared to leave.

The Yankees, with owner Hal Steinbrenner, president Randy Levine and Cashman on the calls, weren’t prepared to make a difficult decision.

Cole had the option of becoming a free agent once the Yankees told him they didn’t want to grant him a one-year, $36 million extension in 2029 – but chose not to do so.

“Maybe the grass isn’t always greener," Cashman said. “I think he’s happy where he’s at. I think he likes our setup. I think he likes who he’s playing for and working for, and I think he likes his teammates. And I think he think we have a legitimate chance to win.’’

The Yankees could have just walked away once Cole exercised his opt-out.

“We didn’t want that," Cashman said. “On our end, on behalf of the Yankees, we certainly wanted him to be with us as we move forward, and he is. And during the conversation it was clear, too, that’s still wanted he wanted. So, the easy solution was to rescind the options."

The resolution prevents the Yankees from having to scour the free agent market to replace Cole, even with Cy Young winners Corbin Burnes and Blake Snell. And they weren’t about to enter the 2025 season with a starting rotation of Carlos Rodon, Nestor Cortes, Clarke Schmidt, Luis Gil and Marcus Stroman.

“Listen, he’s one of the best starting pitchers in baseball," Cashman said. “Has been. He knows us. We know him. One certain thing we can count on is that New York is not too big for him. His work ethic is second to none. His prep is second to none. So, we are really just comfortable to have him still in play for us.

“We can try to build around him and [Aaron] Judge. My main focus right now is trying to find as much talent as we possibly can to find to improve our chances in ’25, but this was certainly a huge important chess piece to retain."

They’re back together once again, and after their interactions during the 48-hour period, they appreciate each other more, too.

“That was a healthy dynamic for us," Cashman said, “for us to land back to us staying together."

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