Yankees Top Latest Offseason Desperation Rankings

The New York Yankees haven't done much with their winter so far, recently signing 2025 Mexican League MVP Nick Torres as, presumably, first base and/or outfield depth, but broadly falling short of their biggest offseason objectives. A recent Bleacher Report ranking spoke to the offseason mood from New York perfectly.

In his ranking of the MLB by desperation for a win this coming year, Kerry Miller of Bleacher Report ranked the Yankees first, citing their aging core of talent (particularly Aaron Judge) and the Los Angeles Dodgers rudely encroaching on their waning "evil empire" reputation.

"But the Yankees take the cake here," Miller wrote. "Their big five is even older than Philadelphia's, they're mired in the longest World Series drought in franchise history and have had to watch the Dodgers usurp their throne as MLB's evil empire. And even after all the spending Toronto has done, the Yankees are on track to spend the most of any AL team for what would be the seventh consecutive season."

Oct 7, 2025; Bronx, New York, USA; New York Yankees outfielder Aaron Judge (99) takes the field prior to the game against the Toronto Blue Jays during game three of the ALDS round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Wendell Cruz-Imagn Images | Wendell Cruz-Imagn Images

"Can they finally get over the hump before Aaron Judge enters his late 30s? Will they finally move on from Aaron Boone if they don't?"

Will the Yankees' Desperation Matter?

The Yankees' fan base clearly feel the desperation and the creep of Judge's finite career, but the organization doesn't seem to feel the urgency they're feeling. If they are, they don't seem to be acting on it. They have been criticized for complacency and for keeping Boone at the helm despite impressive but not championship-winning performances year after year, and this winter so far makes 2026 look grim for the Bronx.

Fans are still holding their breath for big offseason splash moves, which are still very possible. Several of the top free agents in this class are still available, and the Yankees are pursuing Cody Bellinger to return to their outfield, hopefully another starter and hopefully some relievers to fix up the bullpen. At the moment, they have been "running it back" but without Bellinger, a team which evidently didn't prove to be a winning formula with Bellinger.

Oct 7, 2025; Bronx, New York, USA; New York Yankees outfielder Cody Bellinger (35) hits a double in the sixth inning against the Toronto Blue Jays during game three of the ALDS round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

In the ranking, the Yankees were grouped with three other teams -- the Toronto Blue Jays, New York Mets and Philadelphia Phillies -- for whom anything short of a World Series win in 2026 will feel like a failure (the Dodgers got a category all their own). Excluding the Blue Jays, these are the teams chasing Bellinger right along with the Yankees, and the ones who have the hunger and the deep pockets to make it to the mountain top this spring. We'll see if the Yankees are willing to keep up with them.

Make sure to bookmark Yankees On SI to get all your daily New York Yankees news, interviews, breakdowns and more!