11 Yankees who shouldn't be back in 2026 after another demoralizing season

Another year, another disappointment. This time, the New York Yankees' playoff run ended early in the ALDS against the division-rival Toronto Blue Jays — the teams' first ever meeting in October. The pain never ends. The Yankees will never learn. Aaron Boone will be managing this team until old age begins to take hold.

Once again, the Yankees will have to completely re-work their roster, which has been a theme for about five years running. It feels like no team in MLB has consistently had to completely remove 10+ players every November except for New York, thanks to shoddy work at the margins by Brian Cashman. That's what happens when your roster is top-heavy and you spend money ineffectively.

Expect a very different 2026 roster that will probably deliver similar, underwhelming results that will waste another MVP-caliber season from Aaron Judge.

11 Yankees who shouldn't be back in 2026 after another stunningly demoralizing season

Braden Shewmake

Cannot believe he's still on the 40-man roster. CANNOT BELIEVE IT. What purpose did this serve? How is this responsible roster management?

Allan Winans

He was once upon a time worth a try after being picked up from the Atlanta Braves. Winans' Triple-A numbers were great. But the Yankees can't hitch their wagon to a guy who gave up nine earned runs on 13 hits and three walks in just 9 1/3 innings this year. Couldn't have made a worse first impression. Find a better fringe roster pitcher.

Jorbit Vivas

Vivas hasn't necessarily gotten the fairest shake (welcome to life as a prospect in the Yankees' organization), but he did not help his case in 2025. Across 29 games, he hit .161 with a .516 OPS and the Yankees completely re-worked their bench/depth at the trade deadline, essentially confirming they couldn't have less interest in Vivas for 2026. Perhaps he remains to hang around at Triple-A, but we'd probably bet on Cashman trading him for something.

Ian Hamilton

Hamilton has done nothing but regress since 2023, and injuries played a big role in that. It's upsetting because he was such a force just a couple years ago. In 2025, the Yankees sent him down to Triple-A right before the trade deadline and left him there for the rest of the year as he finally stayed healthy. If that doesn't say "we're done," we're not sure what does.

Paul Blackburn

He was here to eat innings, and nothing more. If he returns in that role, the Yankees will have not learned a single thing (quite possible!). Blackburn was a means to an end once the front office made their bed with this terrible bullpen. There's no reason not to upgrade over a pitcher of this caliber if you can.

Jonathan Loaisiga

A complete waste of $5 million. The Yankees didn't learn their lesson, but this was perhaps the final straw. Loaisiga has an option for 2026 that will almost assuredly get declined unless Cashman really wants to prove he's the most stubborn executive out there. Loaisiga has done nothing but hurt this team every year with the exception of 2021. It's time to say goodbye.

Austin Slater

Acquired for a top prospect at this year's trade deadline to address the need for more right-handed hitters after YEARS of a lack of lefties, Slater logged just 25 at-bats because he immediately suffered a hamstring injury and missed a month. He wasn't on the Wild Card roster, so we don't see a world in which he returns, especially with Spencer Jones in line to come up in 2026.

Trent Grisham

Initially, Trent Grisham did not crack this list because of his tremendous career year. It was a sight to see, and it further validated the team's decision to push for last year's Juan Soto trade. The problem? Grisham is hitting free agency and will probably be looking to get paid. Who can blame him?

But the Yankees probably weren't going to pay big money for a veteran outfielder, at least on a long-term deal. And if that's the case, they'd probably prefer Cody Bellinger. The next option? Give Grisham the $22 million qualifying offer. That'd keep him in town for 2026 and let him hit free agency again next November. What was once a sound decision now looks like irresponsible spending after he just hit .138 with a .207 slugging percentage and 10 strikeouts. They'd probably rather save that money and see what Jasson Dominguez and Spencer Jones can do.

Luke Weaver

This will make us sad, but it's certainly trending in this direction. Weaver was awful in the month of September and then he blew Game 1 of the Wild Card Series against the Red Sox after Max Fried's sterling start. There was no room for error, and Weaver made every possible misstep to surrender the lead (which eventually sealed the loss). He didn't necessarily have a bad season, but the Yankees got the most out of him by investing the least possible amount. Now that his numbers have improved, another team won't hesitate to spend a few million to fortify their bullpen. He might even want to be a starter. Weaver can still succeed as a back-end reliever, but his rollercoaster 2025 ended in the worst way possible, and the Yankees probably won't want to extend the relationship.

Devin Williams

One of the worst trade acquisition of Brian Cashman's Yankees tenure, Devin Williams has as close to a 0% chance of returning as he possibly can. Though he's rebounded and proven to be valuable in pockets, he was supposed to be the best (or one of the best) relievers in the sport. Instead, the Yankees got his career-worst season, headlined by a 4.79 ERA. He might get paid, but it won't be in the Bronx.

Mark Leiter Jr.

The Yankees can no longer carry a reliever who doesn't have a clear role in the bullpen — especially someone who is supposed to be a veteran presence. Leiter Jr. has done his best since being thrusted into high-leverage at last year's trade deadline, but he just wasn't good enough. A 4.89 ERA and 1.59 WHIP in 80 games since arriving in 2024 is as underwhelming as it gets, and the Yankees showed a lack of faith in him down the stretch this year. Expect a non-tender.