To be honest, in the end, the money left on Gerrit Cole’s contract is not the Yankees biggest problem, His absence obviously will be. In conjunction with fellow Yankee pitcher and AL rookie of the year Luis Gil also gone for a significant period, it’s devastating.

The Yankess have complained several times about how they were dissed by the Dodgers after being dispatched from last year’s world series. The fact of the matter is the Dodgers have simply set themselves up better.
The Dodgers can afford to hold back Shohei Ohtani until he’s ready to pitch again by having a number of more than accetable replacement arms, like Dustin May, Tony Gonsolin and Landon Knack. The Yankees have no such fall back plan.
Yanks Due diligence on Cole?
The Yanks had a moment there to avoid the financial pain that Cole’s Tommy John surgery will deal them. In November Cole triggered a contractual opt-out that could have made him a free agent.
At that point the Yanks were free of his contract. They were now free to make sure he was healthy before committing to any further cash outlay.
You didn’t have to go very far to see other teams doing their due diligence especially on pitchers. Jeff Hoffman had two teams rip up proposed free agent deals based on what they saw on his pre signing physicals.
Though the Blue Jays signed Hoffman for three years, it was for a modest $11 million per season
Cole arm problems in 2024
There is no greater indicater of future injury than the past. And in Cole’s case it’s the recent past. Not only that but since he pitched for your team than you’ll know more than anybody else.
After Cole’s sudden opt out, all the Yanks had to do was make sure that arm was sound. Especially since last spring, Cole was shut down early in camp with elbow inflammation. He would make half his usual starts in 2024.
So there were the Yankees with a chance to make sure their future investment would be sound. Instead however, The Yankees and Cole agreed to continue with their deal as it was originally constituted, meaning that the right-hander is still signed to a contract with $144 million remaining through 2028.
He won’t pitch in 2025 and just how many innings he’ll give them and how effective he’ll be in 2026 is very much up in the air, as is the Yankees world series aspirations without their ace or suitable replacements.