After a strangely regressive year in some departments, Gerrit Cole has been an ace's ace for the 2023 Yankees. He's kept the ball in the ballpark, allowing just 15 homers after leading the league with 33 surrendered last season. He's been a stopper, winning after every single loss that preceded one of his starts (until Monday in Chicago, unfortunately). He's gone deep into games. He hasn't sold out for Ks. He's the Cy Young front-runner for a moribund Yankees team that's desperately needed him all year long.
And he can opt out of his contract after the 2024 season, potentially robbing the Yankees of one of the very few good things they've currently got going.
Will Cole opt out? That's difficult to assess, but the rule of thumb surrounding these types of contract provisions is that if the pitcher negotiated them, they'll probably use 'em.
Luckily, for the Yankees, Cole doesn't have all the agency in these proceedings. If he does trigger the opt-out, removing his age-34-through-37 seasons from the contract, Hal Steinbrenner has the option to tack an additional year onto the deal and keep Cole in place.
Which brings us to the toughest point of all ... what will the Yankees be after 2024? What do they intend to be in 2025 and 2026, as Cole's theoretical "prime" likely wraps? Will they be a team that needs an ace on a hefty, but still reasonable, contract? Or will they view a $36 million expenditure for an ace as an unnecessary luxury, as lipstick on a proverbial pig? You wouldn't think the Yankees would intentionally take a step back, but if their next championship window coincides with Cole's decline rather than his prime ... wouldn't Steinbrenner and Brian Cashman (God, it's really still going to be him, isn't it?) have to think long and hard about whether they'd respond to Cole's demands with a $36 million chunk for a 38-year-old?
Will Yankees pay for Gerrit Cole's decline after he exercises contract opt-out?
Remember how crucial 2022 felt, with Aaron Judge's departure looming? 2024 is going to feel the same way. If the team is competitive and feels ascending, doing whatever it takes to keep Cole in place will be a no-brainer. If the team takes another step or two back, the Yankees might decide Cole's prime years would be better spent elsewhere, especially considering whatever his next contract is will undoubtedly take him through something approximating the end of his career, too.
A fan, with no skin in the game, can easily dismiss these concerns. "Do you want Prime Gerrit Cole? Great. Then pay him whatever it takes to keep the status quo."
An owner with tons of skin in the game, who's already been lambasted for giving a ~$290 million budget to a GM who can't find balance? He'll have to think long and hard about whether Cole, who'd obviously make the 2025 and 2026 rosters better, will make them strong enough to matter.