Though the New York Yankees certainly pivoted nicely after Juan Soto’s departure, many would argue they did not do enough. And it’s hard for anybody in opposition of that viewpoint to rebut, considering Brian Cashman literally halted meaningful transactions after adding Paul Goldschmidt in late December when various roster issues still existed (and continue to exist today).

The Yankees’ offseason plan was to build an embarrassment of riches on the pitching side because they knew they were not effectively finding a one-for-one (or even two-for-one) Soto solution. So when Max Fried and Devin Williams were acquired, fans started to buy in.

Swapping Williams for Clay Holmes was the upgrade of all upgrades, and it shifted Luke Weaver down to setup man. There now existed a roadmap for the Yankees to build a bridge to the eighth and ninth innings.

For the rotation, Fried represented a co-ace alongside Gerrit Cole, with the sweetener of everybody forgetting that was supposed to be $162 million man Carlos Rodón’s job. At least, that was the case at that point in time … because it’s hard to believe the Yankees didn’t have any Cole fears in the back of their minds after what had happened in 2024.

Yankees likely had Gerrit Cole fears in mind when they made Max Fried contract offer

Is it possible the Yankees went the extra mile with Fried and gave him a record-setting contract for a free agent left-handed starter because they foresaw potential doom with Cole and figured Fried would earn his paycheck filling in as the No. 1 starter for portions of 2025 and into 2026? It’s worth pondering, especially after finding out the Yankees have insurance on Cole’s contract.

“The Yankees have insurance on Gerrit Cole, which is a positive thing in a very worrisome situation. They say it’s ‘good’ insurance, but they don’t want to talk about it more in hopes they don’t have to make a claim,” Jon Heyman of the New York Post wrote.

And don’t forget about Cole’s whole opt-out saga at the beginning of the offseason, when he tried to squeeze another $36 million out of the Yankees despite only pitching half the year with elbow troubles. Cole quickly opted back into the remaining four years and $144 million on his deal (assuming because the Yankees left it on the table) when the team made it clear they wouldn’t be committing to anything beyond that.

Fast forward about a month to December, and the Yankees went up to eight years and $218 million for Fried, essentially tacking on what should’ve been an extra year and $36 million for Cole based on the opt out terms. In the Yankees’ eyes, that wasn’t “adding” money to the payroll — it was a version of offsetting expenses over the long haul and insuring themselves against a fairly likely devastating injury.

While Fried could’ve been viewed as a “juggernaut” addition in more ways than one, it’s clear the Yankees’ worst-case scenario was being content with him as their ace if Cole went down. And in their eyes, that keeps them “in contention” without having to go the extra mile.

While nobody foresaw absolute disaster striking in the middle of spring training, there’s no denying the Yankees left themselves exposed to quickly turn from “division favorite” into “Wild Card hopeful.”