One Yankees Free Agent They Can't Afford to Lose (and One They Can)

Of the Yankees' upcoming free agent class, there is one who needs to return to the Bronx.

Yankees GM Brian Cashman has one free agent he can't afford to let walk, and another whose departure won't upset many fans. | USA TODAY Sports via Reuters Connect

With the New York Yankees' 2026 season in the books, they will now begin a busy offseason that may involve moving on from past contributors.

After the World Series concludes, 10 players on the Yankees' roster will become unrestricted free agents (h/t Yankees Worldwide). The most noteworthy Yankees hitting the market are outfielder Trent Grisham, infielder Jazz Chisholm Jr. and relief pitcher David Bednar; all three of these players were acquired in trades and became key contributors to the team at varying points during their tenures.

New York Yankees impending free agents:

2B Jazz Chisholm Jr.
"CF" Trent Grisham
1B Paul Goldschmidt
"3B" Amed Rosario

RHP David Bednar
RHP Paul Blackburn
RHP Tim Hill
LHP Ryan Yarbrough
RHP John Schreiber
RHP Michael Fulmer

Who would you let walk in the offseason?#Yankees pic.twitter.com/gSWTCfF0pi

— Yankees Worldwide (@NYYWorldwide) October 8, 2026

Ironically, the player the Yankees would want to bring back most is the one with the most limited role, and that is Bednar. He had a much stronger 2026 season compared to Grisham and Chisholm, and while it's foolish to compare a closer to position players, Bednar provided the Bronx Bombers with something the other two couldn't.

Yankees need David Bednar for bullpen stability

Compared to the starting rotation, the bullpen was the far weaker component of the Yankees' vaunted pitching staff. Many relievers dealt with inconsistency or outright ineffectiveness over the course of the season. However, Bednar was the exception during the stretch run.

The right-hander, who turns 32 on Saturday, admittedly struggled during the early going by allowing 11 earned runs over his first 20 appearances for a 4.95 ERA. But from May 18 onward, Bednar was automatic. He converted 25 of his last 27 save opportunities and logged a 1.46 ERA with 53 strikeouts across 49.1 innings, as well as pitching three scoreless innings with a trio of strikeouts in the postseason (h/t Lucas Parmenter).

David Bednar gets his second K of the game to end the inning #Yankees pic.twitter.com/cGXOgXfD47

— Lucas Parmenter (@LucasSports19) October 8, 2026

Bednar also proved capable of entering in the eighth inning to nail down victories, further bolstering his value to the bullpen.

Since Mariano Rivera retired, the Yankees have searched for a consistent closer. Aroldis Chapman and Clay Holmes had a few strong seasons but ultimately couldn't be trusted by the end of their Yankee tenures, and Devin Williams was so ineffective last year that he lost the closer role mid-season. Bednar, even with his slow start to 2026, seems to finally be the closer the Yankees are looking for due to his resilience and steady improvement as the games became more important.

The Yankees still need to improve the bullpen over the winter, but part of that equation involves bringing Bednar back in free agency. He's been their most dependable closing option in years, and letting him walk would leave the bullpen in rough shape.

As for who can be shown the door...

Yankees can let Trent Grisham walk without hesitation

In sharp contrast to Bednar and even Chisholm, who could be a rebound candidate, the Yankees will not lose any sleep over letting Trent Grisham go.

In fact, they might be losing sleep over giving him the qualifying offer last winter, as Grisham accepted it to earn $22.025 million for the 2026 season. The 29-year-old bet on himself to replicate his breakout 2025 season, and he wouldn't come close.

Trent Grisham's severe regression in 2026 left a bitter taste in the Yankees' mouths. | IMAGN IMAGES via Reuters Connect

Grisham still showed flashes of his 2025 form, particularly with clutch home runs in the late innings of games, but he proved entirely ineffective as a leadoff hitter by batting just .199 with a .303 on-base percentage at the top of the order.

Further compounding the regressed bat was poor center field defense, which itself was exacerbated by two hamstring strains that required two trips to the injured list.

Yankees season ends after Trent Grisham watches a pitch he should have challenged and then swings at one in the other batter's box pic.twitter.com/li2hxSMjtr

— Talkin' Yanks (@TalkinYanks) October 8, 2026

With Spencer Jones steadily adapting to MLB pitching, he looks ready to be an everyday player in 2027. Even if his defensive metrics in center field have also been poor, the revelation of Jones makes it much easier for the Bronx Bombers to move away from Grisham this winter.

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