Where will Josh Donaldson rank among the worst trades in Yankees history?

With each passing day, this moves up on Brian Cashman's list of unforgivable blunders.

New York Yankees v Colorado Rockies
New York Yankees v Colorado Rockies / Dustin Bradford/GettyImages

A few months ago, we ranked the New York Yankees-Minnesota Twins "blockbuster" trade involving Josh Donaldson and Isiah Kiner-Falefa as the eighth-worst in franchise history. That's probably right. But where does Donaldson rank on the "individual acquisition" level?

This week it was revealed Donaldson's recently suffered calf strain could sideline him for the remainder of the 2023 season. Even if it technically doesn't, there's no reason for the Yankees to welcome him back into the fold for a couple of weeks in September. His contract expires at the end of the year and he's not coming back.

Oswald Peraza is here and it's time to give him as much run as possible to see what the future might hold. And even so, Donaldson has been a weight on this team for the better part of a year now. Actually, there's an exact inflection point: the day he caused a benches-clearing incident with the Chicago White Sox by calling Tim Anderson "Jackie."

Since then, he's been utterly useless. Save for one walk-off grand slam against the Rays, nobody can think of a memorable moment from Donaldson. who will more than likely finish his Yankees career with a line of .207/.293/.385 with 25 homers, 77 RBI, 180 strikeouts and a 92 OPS+ in 165 games. All of that for $50 million. That OPS+ seems high.

Some might argue Joey Gallo was technically the worst because Brian Cashman gave up four prospects for the worst 140-game stretch in Yankees history, but there are other factors to consider.

Is Josh Donaldson the worst Yankees trade acquisition of the Brian Cashman era?

First, you have the money. Inheriting Donaldson's $50 million has very clearly held the Yankees back in their other endeavors. There were a ton of better players available for money alone the offseason the Yankees traded for Donaldson -- which, again, was a deal made because Cashman couldn't admit defeat on Gary Sánchez. This all could've been avoided if Sánchez was non-tendered and the Yankees saved ~$10 million instead of adding ~$50 million.

Freddie Freeman. Marcus Semien. Corey Seager. Kyle Schwarber. Kevin Gausman. Nick Castellanos. Carlos Correa (assuming Scott Boras would've made a similar deal with the Yankees to the one he made with the Twins). This team would've been exponentially better with any of those players, minus Donaldson, and rearranging the deck to figure out another infield formation.

Instead, the Yankees acquired Donaldson, watched him put forth a career-worst season that featured one of the biggest year-to-year drop-offs you'll ever see, and then ran it back with him in 2023, only for it to get worse.

Bad luck? Maybe part of it. But you all saw him whiffing at 94 MPH middle-middle fastballs over and over again. And fans can't help but think Donaldson's money played a role in the Yankees halting their endeavors this past offseason to add after Carlos Rodón signed. Remember that? They "weren't done" ... and then just were.

The frustrations with Gallo were similar, but also different. In their heart of hearts, the Yankees knew what they were getting in Gallo. The warning signs were there: "fit" in New York, ridiculously high strikeout rate, another redundant three-true-outcomes player; unenjoyable to watch. But the thought of adding him to a lineup that ostensibly featured better protection was enticing.

Donaldson was a former MVP. He was coming off a season where he slugged 26 homers and finished with an .827 OPS and 127 OPS+. He got MVP votes in 2019! And then ... poof ... just like that, he was nothing. A liability on one side of the ball, and then, soon enough, on both sides. The locker room issues and distractions he caused with the Anderson incident and this year's "long talk" with Aaron Boone before a game that delayed the manager's press conference did nothing but put the Yankees in a worse position. But the warning signs were at least there for those kinds of things! He's spent his career as an agitator and as recently as 2021 called out the YANKEES' highest-paid player in Gerrit Cole. But Cashman went after him anyway.

The Twins dumped a sunk cost of epic proportions on the Yankees and torpedoed two of their seasons. Don't forget, Donaldson went 5-for-29 with 16 strikeouts in his nine postseason games last year, too.

Gallo was terrible, but the Yankees only had to endure him for two half-seasons, and at the end of the day, he was expendable because he wasn't making a ton of money. Donaldson was almost just as bad of a player, a more prohibitive expenditure, and a costly distraction. At least Gallo was left-handed.

Might have to move this Cashman blunder up a few spots in the infamous annals of Yankees history.