Does Brian Cashman’s job hinge on a Yankees World Series appearance?

Feb 24, 2021; Tampa, Florida, USA; New York Yankees general manager Brian Cashman looks on during spring training workouts at George M. Steinbrenner Field. Mandatory Credit: Kim Klement-USA TODAY Sports
Feb 24, 2021; Tampa, Florida, USA; New York Yankees general manager Brian Cashman looks on during spring training workouts at George M. Steinbrenner Field. Mandatory Credit: Kim Klement-USA TODAY Sports /

After the 2022 season ends, the New York Yankees will see a number of big names hit free agency. Aaron Judge, Anthony Rizzo, Aroldis Chapman, Jameson Taillon, Zack Britton, Chad Green and potentially Luis Severino might all be hitting the road.

Oh yeah, and there’s one more on the business side. General manager Brian Cashman will see his five-year contract with the team expire, which will leave the Yankees with a tough decision. Do you maintain the status quo (that hasn’t really gotten you much of anywhere since 2004) or do you bring in new blood to usher in a new era?

But here’s another question: was the lack of marquee free agent signings this past offseason and trade acquisitions before this year’s deadline, as well as the organization’s desire to hold onto its top four prospects, a sign of the Yankees possibly moving in a different direction? Or, was it just the Yankees insuring themselves in the event the team didn’t make a World Series run in 2022?

Just take a peek at the Yankees’ payroll situation for the next few years. The only players guaranteed contracts beyond 2023 are Gerrit Cole, Giancarlo Stanton, DJ LeMahieu and Aaron Hicks. Cashman’s responsible for all of those deals (though he acquired Stanton’s contract) and only two are viewed favorable at the moment (Stanton and DJ).

He failed to sign Judge before the season started. He’s failed to acquire adequate starting pitching for YEARS now. His extensions for Hicks and Severino have been disasters. His Gleyber Torres-shortstop experiment set the Yankees back years. His obsession with keeping Domingo Germán on the roster objectively makes this team worse.

We can commend him for plenty of great moves he’s made … but the flops have been that much more glaring. Sonny Gray, Joey Gallo, JA Happ, Josh Donaldson, Andrew Heaney, Aroldis Chapman, Clint Frazier, Corey Kluber, Zack Britton, James Paxton, Adam Ottavino, Lance Lynn, Jacoby Ellsbury, Brian McCann … did we miss any? That’s all just since 2010, by the way, with many other minor transactions and colossal free agency misses in between.

Is Brian Cashman’s job on the line if the Yankees don’t make the World Series?

This is the third straight year where the Yankees have, on paper, appeared to be the “favorite in the American League.” The 2020 season was a spectacular failure, but not nearly as bad as 2021. Now, though things went very smoothly in April, May and June, this has been a very different team over the last two months. And the bad trade deadline vibes aren’t helping.

The Yankees are a corporate machine, so it’s not exactly characteristic of them to boot someone out of the job after two-plus decades … but doesn’t winning trump consistency? Sure, Cashman’s never overseen a losing season, but only one time has “his” collection of players and transactions won a World Series.

When he took over in 1998, the nucleus and core of the team was already built. The three World Series wins and five overall appearances were largely due to what was in place thanks to Gene Michael and Bob Watson.

He did make some trades that propped up some of those title-winning teams (David Wells, Roger Clemens), but his history of drafting has been ABYSMAL and his aggression in free agency has left a lot to be desired for what’s expected of the Yankees. New York has one World Series over the last 21 years. That could change this year, but many aren’t sold after how the deadline ended.

Just look at the players under contract and the recent commitments ownership has allowed Cashman to make. There’s no long-term imprint on this roster that ties him to the organization beyond 2022. Stanton and Cole are here for a while, yes, but, at this point, it’s fair to say neither are overly integral to the success of this team (the Yankees made two ALCS’ without their contributions and have largely fallen short of the main goal since they arrived).

With their beloved top prospects in tow after surviving the trade deadline, that might’ve been the final sign that Cashman’s future in New York hinges on at least an appearance in the Fall Classic. Anything less is an abject disappointment, but you (and the Yankees) already knew that.

Being reminded for the 13th straight year might be the final straw.