If Gerrit Cole were a free agent, would the New York Yankees sign him to a five-year, $180 million deal covering his ages 34 to 38 seasons?
In a vacuum, the answer probably is no. The Yankees, though, are not operating in a vacuum as they ponder whether to void Cole’s decision to opt out by adding another $36 million year on his contract, a determination they must make by Monday night.
So while the rational decision seemingly would be for the Yankees to decline committing to Cole for his age-38 season and send him hurtling into free agency, it would be an upset if that was their actual move.
If the Yankees lose Cole, their 2025 rotation would be down to Carlos Rodón, Clarke Schmidt, Luis Gil, Nestor Cortes and Marcus Stroman. And while the free-agent market is deep in top starting pitchers, from Corbin Burnes to Blake Snell to Max Fried, all come with their own questions, as pitchers always do.
Cole has been a Yankee for five seasons. Their doctors have unique insight into the condition of his arm. As long as they believe Cole is not necessarily headed for a major elbow injury, he is probably as safe a bet as anyone they could sign in free agency or grab in a trade.
The reputation of Yankees owner Hal Steinbrenner also plays into this. Only the New York Mets and Los Angeles Dodgers carried higher payrolls than the Yankees last season, but a perception exists — mostly among fans, but even among some in the industry — that Steinbrenner should spend more.
Steinbrenner, in theory, could rationalize losing Cole by saying it would make more money available for the team to retain free-agent outfielder Juan Soto. But that argument would fall flat if the Yankees lost Soto, leaving them without two pillars from a team that won the 2024 American League title. Steinbrenner has the money to keep both Cole and Soto. A decision to walk away from Cole only would increase the pressure on the owner to sign Soto. And if he lost both . . . hoo boy.
Cole, then, is the proverbial bird in the hand, and to a degree, five years, $180 million is the going rate for a pitcher of his caliber. Two years ago, the Texas Rangers signed Jacob deGrom — a pitcher who was a year older than Cole and had a far more extensive injury history — to a five-year, $185 million free-agent deal.
The deGrom contract, to this point, has not worked out well. He required a second Tommy John surgery in his first year with the Rangers, and over two seasons has made only nine starts. Of course, calamitous outcomes of that kind are not uncommon with long-term deals for starting pitchers, and deGrom was a higher risk than most.
Cole, upon returning from his elbow issue, made 22 starts, including the postseason, and sustained his elite performance through the end of the World Series. Which isn’t to say his journey was always smooth. The Yankees scratched him from a start against the Philadelphia Phillies on July 30, citing “general body fatigue.” In the postseason, he didn’t throw more than 89 pitches in a start until his final outing, Game 5 of the World Series.
Obviously, Cole’s risk of injury is higher than it was before he went on the IL with an arm problem for the first time since 2016. But the Yankees, because of their financial might, are better positioned than most clubs to absorb that risk.
The Yankees, then, would appear backed into a corner. They could attempt to restructure Cole’s deal, guaranteeing him more money but deferring part of it to reduce the short-term financial hit and lower the pitcher’s luxury-tax number. But agent Scott Boras, in explaining why Cole in 2019 chose the Yankees’ $324 million contract over a $300 million offer from the Dodgers that included deferrals, recently told The Athletic’s Andy McCullough, “In the free-agent market, the issue always is, when you’re offering money, it has to be real money, not deferral money.”
Cole technically is not yet a free agent, but he has taken the first step, daring the Yankees to ante up. By opting out, he knew he might sacrifice his remaining $144 million guarantee over four years. And if the Yankees refuse to tack on the extra year, some might interpret their decision as a vote of no-confidence in Cole’s ability to stay healthy, compromising his leverage in the open market.
It’s a dangerous game for Cole in other ways, too. At his introductory conference, he brought out the cardboard sign he made for the 2001 World Series, when he was 11: “Yankees fan today, tomorrow, forever.” He is popular with fans, a valued presence in the clubhouse, an important part of a team that just made it to the World Series. Does he really want to go somewhere else? It’s at least possible now.
Boras and Cole, though, likely would be undaunted if the Yankees pulled the plug. To come out ahead, they would need to beat a $144 million guarantee. No sure thing, considering the time Cole missed in 2024. But all it would take is one team willing to make that investment. And chances are, that club would be a big-market contender, too.
The Yankees, when they included the unusual opt-out language in Cole’s contract, knew they eventually would reach this juncture. To an extent, they’re damned if they keep him and damned if they don’t. It was the price of doing business with Cole in 2019. It’s the price of doing business with him now.
(Top photo of Gerrit Cole: Luke Hales / Getty Images)
