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3 worst moves Brian Cashman has ever made with Yankees

By Zachary Rotman

Oct 17, 2019; Bronx, NY, USA; New York Yankees general manager Brian Cashman talks on his phone during batting practice before game four of the 2019 ALCS playoff baseball series against the Houston Astros at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports
Oct 17, 2019; Bronx, NY, USA; New York Yankees general manager Brian Cashman talks on his phone during batting practice before game four of the 2019 ALCS playoff baseball series against the Houston Astros at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports /
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Oct 20, 2022; Houston, Texas, USA; New York Yankees third baseman Josh Donaldson (28) strikes out during the fourth inning against the Houston Astros in game two of the ALCS for the 2022 MLB Playoffs at Minute Maid Park. Mandatory Credit: Thomas Shea-USA TODAY Sports /

In what has been a very long and successful tenure as Yankees General Manager, Brian Cashman has made some questionable decisions. Here are the three worst ones.

Brian Cashman has been the General Manager of the New York Yankees since 1998. Since taking over, the Yankees have won six AL Pennants and four World Series titles. They make the playoffs virtually every season and have finished over .500 in every season since he took the GM job.

Even with all of this success, no General Manager is perfect. Some moves Cashman has made haven’t worked out the way he envisioned. Let’s look at the three worst.

Brian Cashman’s worst Yankees moves: The Josh Donaldson + IKF Trade

Last offseason, the Yankees acquired Josh Donaldson and Isiah Kiner-Falefa in a trade with the Minnesota Twins. At the time, this trade did make some sort of sense for New York but it has aged very poorly.

The Yankees added IKF to be a stopgap at shortstop. They for whatever reason were enamored with his game, and adding him gave their young prospects Anthony Volpe, Oswald Peraza, and Oswaldo Cabrera, more time to develop in the minors.

Kiner-Falefa slashed .261/.314/.327 with four home runs and 48 RBI this past season for the Yankees. His bat was never great, but not hitting your first home run until mid-August despite playing half of the time in The Bronx isn’t a great look.

The Yankees did acquire IKF for his glove. He won a Gold Glove with Texas during the shortened 2020 season but did so as a third baseman. His defensive metrics at shortstop were never close to as good as they were at third, and IKF wasn’t great at short with the Yankees either. He had 15 errors at shortstop and a whole bunch of low throws saved by Anthony Rizzo at first. He ranked in the eighth percentile in OAA according to baseball savant. He was a below-average shortstop for New York.

Josh Donaldson was supposed to be an upgrade over Gio Urshela who was coming off a down year. Donaldson was at one point in time one of the most feared hitters in baseball and even won an MVP award. He was clearly in decline but hit 26 home runs and had a 127 OPS+ in 2021. He was still a legitimate threat at the plate. Well, until the Yankees got their hands on him.

Donaldson slashed .222/.308/.374 with 15 home runs and 62 RBI this past season. He had a 94 OPS+ which is the worst mark in a full season of his career. He was a complete non-factor in the playoffs, recording one hit in 13 at-bats including 10 strikeouts. To make matters worse, Urshela had a 121 OPS+ for Minnesota.

The Yankees took on a ton of salary in this trade and helped the Twins open up money to sign Carlos Correa. I’m not saying the Yankees beat Houston last season, but if Correa and Urshela made up their left side of the infield over IKF and Donaldson, they most certainly wouldn’t have been swept in the manner that they were.

The Yanks are likely going to start one of their young guys at short to begin the year but have Donaldson at third still. Here’s hoping for a better year.

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