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The Yankees cannot repeat this fatal mistake from the 2025 offseason

January 27, 2026 by Empire Sports Media

MLB: Spring Training-New York Yankees at Baltimore Orioles
Kim Klement-Imagn ImagesKim Klement-Imagn Images

When the Yankees rolled into camp last year, they did so without a surefire option at third base, opting to use Oswaldo Cabrera as the primary starter with one of Oswald Peraza and Pablo Reyes platooning with him.

If those three could not flourish, then DJ LeMahieu was working back from injury as a potential ‘insurance’ option which worked about as well as you expected.

A bad situation turned into disaster when the Yankees had to move LeMahieu to second base due to physical limitations, resulting in the infield defense briefly collapsing as they hadn’t prepared Jazz Chisholm to play third base again.

This was one of the bigger embarassments for the organization in the last few years, a failure in both roster construction and team-to-player communication, and it’s one they need to avoid for 2026.

New York still has some manuevering it must do this offseason in order to say they checked their boxes for this winter, as they must avoid making the same mistake from last winter by punting positions of significance.

READ MORE: The Yankees might have struck gold with super-utility man Jose Caballero

Ignoring the Yankees’ Obvious Need in the Bullpen Would Repeat Their 2025 Third Base Failure

MLB: Playoffs-Toronto Blue Jays at New York Yankees
Credit: Brad Penner-Imagn Images

Paul Blackburn is the biggest addition the Yankees have made to their bullpen this offseason, and it’s not as if this is a group that retained all of its key pieces from 2025.

Devin Williams and Luke Weaver remained in New York, but that’s because they’ve signed with the Mets, leaving this bullpen without two high-whiff pitchers.

There’s too much uncertainty in this bullpen, relievers are volatile on a year-to-year basis but this bullpen will almost certainly suffer the same command issues they dealt with last season.

Critical games were lost on inexplicable free passes because a lot of pitchers on this staff are not reliable strike-throwers, and there wasn’t enough reliability for Aaron Boone to know which button to press on a night-to-night basis.

It reminds me of last year’s infield situation too much; the Yankees let Gleyber Torres walk with zero intention of re-signing him, but they didn’t add a fourth infielder to offset his loss.

MLB: ALCS-New York Yankees at Cleveland Guardians, gleyber torres
Credit: David Dermer-Imagn Images

Had they returned Torres and moved Chisholm to third base there would have been defensive challenges for this infield, but the Yankees almost certainly win more games and have a more balanced lineup.

We can all point out the flaws in his game, he’s slow and doesn’t field the ball well while making multiple mental gaffes a season that can drive you crazy.

That imperfection does not outshine his strong contact abilities from the right-handed side, and they ultimately had to pay both money and prospects for Ryan McMahon.

By not paying free agent relievers the Yankees are not being ‘smart’ with their financial expenses, they’re just putting more pressure on their farm system to produce tradeable talent to improve the bullpen significantly.

At least this time there are still solid veteran arms who can improve this bullpen for cheap that still remain available on the free agent market.

MLB: Wildcard-Boston Red Sox at New York Yankees
Credit: Brad Penner-Imagn Images

You can scream to the hilltops that Justin Wilson or Danny Coloumbe are too old for the Yankees to consider if they sign elsewhere, but this kind of pickiness is how the organization ended up with a disgusting fourth infield situation last year.

Beggars cannot be choosers; this bullpen needs an addition and if Wilson is the best they can do then so be it, it’s better to add someone who has flaws than it is to stand completely pat.

The swing-and-miss stuff that Wilson specifically brings should be appealing to a contender, he struck out over 27% of batters faced last season with a 46% GB%, throwing two different fastball shapes with a slider and splitter as well.

I know his 2021 stint with the Yankees went poorly, but that’s another nitpick that would just get in the way of making the team better when the alternative is likely just doing nothing.

This is an addage I’ve repeated several times on the Fireside Yankees Podcast, but checking your boxes is important; the Yankees failure to just add a replacement-level infielder last year cost them the American League East.

MLB: World Series-Los Angeles Dodgers at New York Yankees, brian cashman
Credit: Brad Penner-Imagn Images

I am fairly pro-Cashman, the long-time GM has produced plenty of excellent rosters and has a storied championship background.

His ability to adapt to modern roster construction throughout the years is impressive, and I think the last 2 squads specifically are some of his best work compared to what we got in 2021 or 2023.

With that all said, it’s undeniable that his infield gaffe from last year is inexcusable even if the budget had closed off; not having the funds to replenish the infield is something he should have planned for in all honesty.

That cannot be followed up with the same kind of mistake in 2026; this roster is not good enough for the Yankees’ franchise and their standards of what it means to contend for a World Series title.

Being slim favorites on FanGraphs in an AL where no team is projected to win over 86 games does not cut it for me in the slighest, and I expect a level of greatness and urgency from the organization to build a proper contender.

I’m aware that a big move is not likely to be on the horizon, but these seemingly minor transactions can decide whether you will or will not play a three-game Wild Card Series.

In an offseason where the Blue Jays lost Bo Bichette while missing out on Kyle Tucker, the Red Sox lost Alex Bregman, and the Mariners have stood mostly pat, the Yankees must push harder to check off all of their boxes.

Filed Under: Yankees

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