Yankees the clear winners after Gerrit Cole’s about-face

SAN ANTONIO — Brian Cashman played nice. He insisted that, yes, Gerrit Cole opted out of the final four years at $144 million of his contract, but both sides agreed to push the original Sunday 5 p.m. deadline back by 24 hours because they truly wanted to extend a marriage, not end it. 

But the only sure way for the Yankees to keep Cole would have been to tack on a fifth year at another $36 million. They retained him instead without adding a penny. Thus, the Yankees might have not played well in the World Series to end their 2024 season. However, they already have their first victory of 2025. 

Cashman talked about the cramped time to get this resolved with Cole from the end of the World Series to the deadline. It is why, he said, when the parties — him, agent Scott Boras and eventually Hal Steinbrenner and Cole — had positive discussions over the weekend, it was agreed to push the deadline to Monday at 5 p.m. 

Cashman mentioned that at a future date the sides can revisit an extension. But why would the Yankees extend Cole now unless it was to add years at less money or deferred salaries to lower the value from $36 million a year to help toward the luxury tax payroll? 

After all, the Yankees faced a pressure point — Cole could go out into free agency — and did not blink. Why blink now that Cole is a signed player for four more years, through his age-37 season, unless it is to their benefit? 

Cashman refused to accept this was a game of chicken that the Yankees won. He said this was what the sides mutually wanted. Well, it certainly was what the Yankees desired. Cole, by opting out, was, at minimum, seeing if the Yankees would buckle. 

They didn’t. Will this convince the Yanks to hold firm with another Boras client, Juan Soto, at what offer they think is proper and see if Soto really wants to stay and/or believes there is a greater market elsewhere? It probably will not work as well. As opposed to Cole and Aaron Judge, Soto does not have deep Yankees roots. Plus, at 26 and the peak of his powers, Soto will have a strong field of suitors and full knowledge of what is possible, in the way that Cole could not in this window. 

Cashman said that adding the $36 million was “not something we were comfortable doing … but we wanted our ace back.” Of course. There is no Ace Depot to replace him. Free agency has some high-end starters in Corbin Burnes, Max Fried, Blake Snell and possibly Roki Sasaki. But the Yankees could not know for sure if they could land any or how any would handle New York. There is no doubt in that area with Cole, who Cashman called “family” in detailing how well the relationship has worked both ways. 

Judge turns 33 in April. The Yankees are a “go for it now” organization. And Cole is a “go for it now” player, who if he performs well the next four years could have his No. 45 retired. Cashman said the Yankees are now again building around the Judge/Cole duo. 

“We wanted our player and our ace back, and he certainly didn’t want to go,” Cashman said in explaining the renewal of vows. 

That is very kumbaya. And probably true. But also true: The Yankees did not want to just add another $36 million to his deal, and Cole could not be positive of who would do what for him in the market. 

Cole turned 34 in September. He just came off an elbow injury that limited him to 19 starts. His 3.41 ERA was his worst since he left the Dark Ages of the Pirates for the new arts of the Astros. His strikeout rate has fallen from 32.0 to 27.0 to 25.4 the past three years. And, if you would like to note the coincidence that the decline is concurrent to a greater crackdown on illegal sticky stuff, go for it. 

If the Yankees had walked away from an ace who has thrived for them, would they have been throwing a caution light up to the rest of the industry? Even if not, is there just a natural caution? Cole has pitched more than 2,000 career innings, including the postseason. Do you think he will be as healthy and successful the next five years as he was from ages 29-33? 

Cole’s No. 1 similarity score through age-33 on Baseball Reference is Max Scherzer. Through age-33, Scherzer had 10-straight 30-start seasons. He had one after that — and, yes, one season that it was impossible to reach the milestone, the pandemic 2020 campaign. Scherzer was still mostly good when he pitched — he just pitched less frequently and with declining sturdiness and impact.