Jazz Chisholm Jr.'s Yankees tenure officially ending perfectly encapsulates Brian Cashman dealings

Jazz Chisholm Jr.'s tenure with the New York Yankees looks like it's officially over. The Yankees did not extend Chisholm a qualifying offer before Monday's 5 p.m. deadline, and now he is a free agent.

Chisholm played himself off the Yankees in 2026, struggling with a .231/.312/.399 slash line, .711 OPS, 19 home runs, 55 RBI, 41 stolen bases and an underwhelming 1.7 bWAR. He also made a crucial throwing error at second base in the ALDS and then doubled down by saying he would probably make the ill-advised play all over again if given the chance.

What was supposed to be an electric walk year with better playoff results ended up being a disaster for both parties. And it pretty much sums up how the Yankees do business.

Yankees GM Brian Cashman acquired Chisholm from the Miami Marlins at the 2024 trade deadline. Unfortunately for fans, this move wound up aligning with the majority of trades that Cashman makes, where the player is good, but not good enough.

More recently, Cashman landed first baseman Luis Garcia Jr. from the Washington Nationals at this past summer's deadline. Garcia had a 0.6 bWAR, .736 OPS and seven homers for the Yankees in 43 games. This is the latest example of a player being solid, but not enough to make the Yankees a World Series title winner.

At first, it appeared that the decision to bring in Chisholm was the right one. He agreed to shift over to third base and hit .273/.325/.500 with a .825 OPS, 11 homers and 23 RBI down the stretch in 2024.

Chisholm's best season with the Yankees came in 2025, where he posted a 30/30 campaign. In 130 games, Chisholm slashed .242/.332/.481 with a .813 OPS, 31 homers, 80 RBI, 31 stolen bases and a 4.1 bWAR. Even with that showing, his overall postseason numbers drag his regular season numbers down. Chisholm was just 16-for-88 (.182) in his 25 playoff games with the Bombers.

The addition of Chisholm didn't help the Yankees get over the hump, and by the time his team control expired he had seemingly overstayed his welcome in the Bronx. Chisholm's antics, such as taking his position with a lollipop in his mouth, was one of several incidents that rubbed the Yankees and others the wrong way.

Does that type of acquisition sound familiar? Aroldis Chapman. Lance Lynn. Aaron Hicks. James Paxton. JA Happ. Sonny Gray. Anthony Rizzo. Joey Gallo. Rougned Odor. Jameson Taillon. Corey Kluber. Josh Donaldson. Isiah Kiner-Falefa. Harrison Bader. Alex Verdugo. Marcus Stroman. Ryan McMahon. Devin Williams. Camilo Doval. All players who possessed a level of talent that provided some promise that could be acquired for the right price in Cashman's eyes ... but none sufficient enough to push the Yankees closer to a championship. That's a long list of misses that have plagued the Yankees since 2018.

Chisholm now hits the free agent market, where he will likely have to accept a one-year prove-it deal in order to rebuild his value before retesting free agency next year. At this point, it's safe to say that his time with the Yankees is over. The writing appears to be on the wall after the Yankees didn't extend a qualifying offer to him on Monday. The Chisholm trade will go down as on-brand for Cashman's underwhelming and risk-averse acquisitions.

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