The Los Angeles Dodgers won the World Series back-to-back in the second year. And some Yankees fans were enjoying the Blue Jays losing. Now that some time has passed, reality has started to set in. That is, the New York Yankees could have been in the same position the Dodgers are right now if they had made one right decision.

Remember a few years ago, when the Yankees tried for Yoshinobu Yamamoto, but were not ready to match LA’s offer and lost? That missed chance is hurting the Yankees more than ever now. But according to Brian McKeon on the Locked on Yankees podcast, the team didn’t learn from their mistakes.

He explained, “They (Dodgers) loaded themselves up with starters. And we all thought about, ‘Oh, this is crazy. How many starters do you need?’ They had just enough pitching… They exhausted every imaginable option to not lose… The Yankees don’t do that. The Yankees get just enough to try and win, and when one of those things goes down, it scrwes them.”

Yoshinobu Yamamoto dominated the 2025 World Series, posting a 3-0 record and a 1.02 ERA over 17 ⅔ innings. He threw a four-hit complete game in Game 2 and then closed Game 7 with 2⅔ scoreless relief innings. His clutch performances helped the Los Angeles Dodgers secure back-to-back titles and earned him Series MVP honors.

Meanwhile, the New York Yankees nearly signed Yamamoto, reportedly offering $300 million, but backed off and settled for Marcus Stroman. The Dodgers outbid them with a $325 million, 12-year contract. That decision left the Yankees without an elite arm when they most needed one.

The Yankees paid the price.

The Blue Jays defeated them in the 2025 ALDS, and the Dodgers triumphed in the World Series. With ace Gerrit Cole sidelined for 2025 due to Tommy John surgery, their rotation looked in shambles, and the postseason push collapsed.

Yamamoto became the symbol of what smart spending and trust in talent can achieve. The Dodgers invested boldly and were rewarded with history, while the Yankees counted pennies and paid pride. Now, Los Angeles celebrates trophies, and New York celebrates what-ifs, a dynasty lost to a discount.

A familiar fix for the Yankees’ familiar problem

Every winter, the New York Yankees promise stability, and every winter, their rotation looks like a group project missing half its members. The names change, the headaches don’t.

Gerrit Cole is recovering, Carlos Rodón is sidelined, and Clarke Schmidt is on the waitlist. Marcus Stroman’s gone, the kids are still learning, and Brian Cashman once again has to answer the same old question: who’s actually going to pitch?

The Yankees enter another uncertain winter with familiar questions surrounding their pitching depth and long-term stability.

Gerrit Cole’s return from Tommy John surgery in 2026 leaves uncertainty around his durability and command. Carlos Rodón is recovering from his own procedure, while Clarke Schmidt’s rehab will delay his season debut.

That leaves Luis Gil, Will Warren, and Cam Schlittler as the bridge, all talented yet largely untested across a full 162-game schedule.

A reunion with Michael King could stabilize that fragile rotation and restore a sense of balance.

King, who recorded a 3.44 ERA over 73.1 innings for San Diego in 2025, has experience under New York pressure. His projected deal of three years and $75 million makes him an attainable, mid-tier target for Brian Cashman’s front office. Pairing King with Max Fried could give the Yankees a steady mix of proven arms and controllable youth, something they’ve lacked for years.

If history has taught the Yankees anything, it’s that potential alone doesn’t win October games. Gerrit Cole and Max Fried can only anchor so much before the cracks start showing again. Maybe Michael King isn’t the flashiest answer, but he might finally stop the yearly guessing.