Yankees' Brian Cashman lost the 2024 World Series during 2021 offseason

Fresh off the heartbreak of losing the World Series, New York Yankees fans might ask themselves, "how did this happen?". There's no one thing to point at - bad baserunning, improper use of the bullpen, or just a straight-up lack of execution are all to blame. It was the Yankees' first trip to the World Series in 15 years and only the second since they lost to the then-Florida Marlins in 2003. These failures, among others, have been all too common during the tenure of general manager Brian Cashman. 

Cashman, the Yankees' GM since 1998 and baseball's longest-tenured GM by over a decade, inherited a dream team from Bob Watson and Gene 'Stick' Michael. They won back-to-back-to-back World Series in Cashman's first three years and then lost to the Arizona Diamondbacks in the Fall Classic in the fourth year. It's been downhill since then, including the reverse sweep in the 2004 ALCS, one of the most shameful moments in Yankees history.

However, the Yankees were in good shape to add another World Series title to their mantle in 2024, and they may have done so if the 2021 offseason had played out differently.

The Yankees badly needed a first baseman for 2022

The Bronx Bombers had acquired Anthony Rizzo at the trade deadline in 2021 because poor planning left them with 34-year-old Jay Bruce and oft-injured Luke Voit handling the cold corner, so they had a decision to make: re-sign Rizzo, or bring in someone else. Once a premium fielder and middle-of-the-order bat, Rizzo flashed warning signs of decline. His power was fading, and opposing defenses had adjusted to his pull-happy approach. 

Thus, the stage is set for the end of the 2021-22 MLB offseason. One of the names available then was Matt Olson, who was coming off a remarkable season with the tanking Oakland Athletics. He was too expensive for the A's to keep, so they made it known they intended to trade him and receive something of value in return. The Yankees did not want to give up the prospect capital it would have taken to obtain Olson, so they stood by and watched as Alex Anthopoulos swooped in and acquired him for the Atlanta Braves. This move sent shockwaves through the baseball world because up until that point, everyone thought the Braves would re-sign their clubhouse leader and future Hall-of-Famer, Freddie Freeman. 

Freeman, who is one month younger than Rizzo, did not show the same decline as the Cubs legend. He won an MVP award in the shortened 2020 season and then finished ninth in MVP voting in 2021, winning a Silver Slugger award to boot. Did Cashman make Freeman an offer? No.

The Yankees preferred to save money; on March 17th, they re-signed Rizzo for two years and $32M, and a day later, Freeman agreed on a six-year $162M deferred money contract (worth around $140M in present-day value) with the Los Angeles Dodgers. 

So what's the big deal? 

The Yankees apparently had budget constraints and could not afford to make an offer to Freeman. And yet, somehow, they took the money they saved by signing Rizzo instead of Freeman and traded for Josh Donaldson, an abject failure in New York despite having a salary of $22M a year. And now, the payoff: Freeman just won the World Series MVP playing against the Yankees. It's hard to imagine the outcome being the same if he were on the other team. 

Cashman has been good enough to avoid getting fired all these years but not good enough to get the Yankees another batch of World Championships. From Hal Steinbrenner's point of view, there hasn't been a straw that broke the camel's back.

Still, it's time for Hal to do what his father would have long ago and fire Brian Cashman. The Yankees haven't won the World Series in 16 years despite consistently being a top-spending team. When that's true, there's no one that needs to shoulder the blame more than the general manager.

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