Father Time catches Yankees ace Gerrit Cole at career crossroads

Months later, that haunting has taken physical form. After awaiting a second opinion, Cole will undergo Tommy John surgery on Tuesday — a sobering reminder that even $324M contracts can't protect pitchers from career-threatening injuries.

In December 2019, baseball existed in a different universe. The Yankees, still smarting from an ALCS defeat to the Astros, responded with their signature move: throwing money at the problem. They secured Houston's ace with a nine-year contract that made Cole the highest-paid pitcher in history.

The story seemed perfect. Cole, a childhood Yankees fan who declined their draft offer in 2008 to attend UCLA, finally donned the pinstripes after accumulating 94 wins and three top-five Cy Young finishes elsewhere.

His New York chapter started brilliantly — finishing among the top five Cy Young candidates twice before claiming the award outright in 2023. Cole posted a 3.12 ERA in his first five Yankees regular seasons, striking out 915 in 759 innings. 

But those numbers tell only part of the story.

For die-hard Yankees fans, one prize remains frustratingly elusive. The championship drought has stretched to 15 seasons since their last title in 2009, and Cole's mission to restore Yankee dominance now faces its greatest obstacle.

Warning signs emerged last spring when elbow discomfort sidelined the six-time All-Star. Diagnosed with nerve irritation and edema, Cole avoided surgery, debuted in June and posted a 3.41 ERA over 17 regular-season starts before delivering a stellar 2.17 ERA in five postseason appearances.

Yet baseball showed its cruelty in the World Series. Despite allowing just one earned run in two starts, Cole lost both games. Game 5's fifth inning proved devastating when five unearned runs — tied for a World Series record — scored after Cole failed to cover first base.

"I gave it everything I had," Cole told MLB.com's Do-Hyoung Park afterward, his voice breaking. "I'll be frustrated — like, every time you have a tough loss, you use it to motivate you. But it's all out there. There's nothing a whole lot more that I could do."

Cole's determination showed in his gutsy 38-pitch inning, securing six potential outs against the powerful Dodgers while his defense crumbled. But Freddie Freeman's two-run double and Teoscar Hernandez's game-tying single broke the Yankees' spirit.

"This is, like, as bad as it gets," Cole admitted. "It's the worst feeling that you can have, especially since you have to keep, sometimes, willing yourself to believe and give yourself a chance."

Now, five months later, Cole faces a devastating setback after surrendering six runs in less than three innings against Minnesota and declaring something wasn't right.

With surgery confirmed, Cole will likely return at age 35 in 2026 — past prime for power pitchers. His fastball velocity has already dropped from 97.7 in 2021 mph to 95.9 mph in 2024, with recovery likely claiming what remains of his prime years.

Sports rarely allow even their greatest stars to dictate their exit terms. For Cole and the Yankees, a painful truth emerges: that split-second failure to cover first base might define his October legacy. 

One mistake could overshadow years of brilliance — $324M spent on a story left incomplete.