Gerrit Cole made no secrets about the duration of his Yankees fandom, from his very first press conference with the team (or, technically, from an old wire photo): Today, Tomorrow, Forever.
But just because the Yankees will never leave his blood does not mean he won't find himself in a position to leave the Yankees before the end of his playing career.
On Wednesday night, Cole's greatness was cemented, as he was finally added to the register of baseball's Cy Young winners after narrowly missing in 2019 (a season where he likely should've beaten his teammate Justin Verlander, but who's counting [us, we're counting]). Cole was, despite Greg Maddux's underwhelming announcement, a unanimous winner. Sonny Gray -- of course -- finished second.
That means, after his finest season as a Yankee -- which just so happened to be the team's worst campaign he'd been a part of -- the ticking clock will now begin, with one year remaining before Cole must decide whether or not to opt out of the remaining four years of his contract in New York.
It stands to reason that the right-hander has earned a raise, even over the exorbitant $36 million AAV he currently enjoys. Will his loyalty to the organization have him unable to trigger the clause and risk leaving his beloved franchise? Will the Yankees do enough to retain the righty's trust during the 2023-24 offseason and beyond? What about on the field? It would stand to reason that, much like Alex Rodriguez in 2007, Cole will remain a Yankee for the duration of his career, no matter the cost. But perhaps Hal Steinbrenner won't think that way.
Yankees ace Gerrit Cole wins first Cy Young. Now, about his contract...
If the Yankees' ace leaves to test the waters, current ownership might see that as a "Get Out of Jail Free" card, the type of opportunity that Giancarlo Stanton's contract doesn't possess.
The more nightmarish the 2024 season becomes, the more harrowing the looming Cole decision will be. The Yankees cannot necessarily control injury spirals, prolonged slumps, and free agent underperformers. But they can assure Cole that they intend to contend, rather than take their foot off the gas pedal during his prime, by making both shrewd, small moves and bombastic additions this offseason. The willingness to absorb mistakes, move on and continue to pursue championships has not been the Yankees' strength in recent years. Instead, they've been known more for allowing past spending to affect future spending, growing more vindictive about the bloated contracts they approved as the years go by. Look no further than the offseason that brought Cole. The only other big-league free agent the team signed was Brett Gardner, on his final one-year deal. That wasn't enough then, and an equivalent won't be enough now, as Cole approaches a pivot point.
After being unfairly dogged by rival fans (and a few fans from inside the house) the first few years of his bloated deal, the right-hander cemented himself as Cooperstown bound with a monstrous cap feather in 2023, topped by the ultimate individual pitching honor.
And, now that Cole has made absolutely certain to capture a prominent place in the franchise's history, it's up to the Yankees to make sure that means "forever."