The complicated retooling of the Yankees’ roster

As we’ve previously discussed, there is no quick and easy fix for the New York Yankees. The voices in the media and podcast sphere can crow all they want about “accountability” and “culture” as pertains to general manager Brian Cashman and skipper Aaron Boone.

At the end of the day, to paraphrase a new book by the great Peter Gammons, it’s all about the players. They’re the ones on the field who need to show up and produce, and the Yankees simply did not this season. And yet, the team still won 93 games, one less than in 2025, and largely without captain Aaron Judge. The three-time MVP missed three months with a broken rib and then missed the last week of the season plus the playoffs with a calf strain.

Add a bunch of, let’s be honest, desperation trades at the deadline to boost a sputtering offense, and now add the impending free agents? The Athletic’s Chris Kirschner did a great job looking at each man hitting the market and if the Yankees should keep them, but this isn’t a simple add/drop issue. What ails the Yankees is largely organizational, systemic, team-wide, whatever we want to call it.

Let’s break each team block down and figure how to, for lack of better word, fix any problems within.

Bullpen

The Yankees’ relievers were the second-best in baseball with a 3.13 ERA, and that’s largely despite the available talent (or lack thereof). The bridge to closer David Bednar was rickety at points, with Cashman’s ability to build a relief corps from scratch on full display. And this despite not adding any bullpen help at the deadline, like the team desperately needed.

Luckily for Cash, this isn’t too difficult. Lefty ground ball specialist Tim Hill will be 37 on Opening Day and lost control of the strike zone in 2026. Re-signing Ryan Yarbrough to fill that role is an option. Cashman could also have some secret data on one of the plethora of lefty relievers on the free agent market and bring in an unknown. Journeymen and late season additions John Schreiber and Michael Fulmer pitched well enough, but not enough to warrant a definite return.

That means the easiest route here is re-signing Bednar despite his velocity dropping. He still managed 35 saves and was all but untouchable in the second half. There is no clear successor on the market or in-house, so keeping Bednar is priority. Retaining Paul Blackburn as a setup man is also an option, but his 93 Stuff+ is below average and unlikely to improve.

Catching

Austin Wells is sticking around despite batting .186 and continued struggles since being a Rookie of the Year finalist two years ago. He fixed his mechanics just enough in the second half that the Wells of old returned, hard contact aplenty. That means all Cashman has to do here is find a righty-hitting catcher who can actually hit, unlike Ali Sanchez. Free agency has plenty of names available here from Tyler Stephenson to Ryan Jeffers to even former Yankee Gary Sanchez.

Simple roster maintenance that won’t be done with much fanfare.

Infield

This one is easy enough to start: Amed Rosario and Jazz Chisholm Jr. are both gone. Rosario barely functioned as a platoon bat all year, and Chisholm is both streaky and moody. The rest of the puzzle isn’t so easy to solve.

Ben Rice will get MVP votes this year, but posted a -5 fielding run value (FRV) at first base. He was largely relegated to DH after the deadline, with newly acquired Luis Garcia Jr. taking over and post a +2 FRV. Re-signing the seemingly ageless Paul Goldschmidt is tempting but, as Kirschner noted, the Yankees don’t need the 39-year-old lefty masher. Rice, who hits lefties well, can take the field then and stick either Aaron Judge or Heliot Ramos in the DH slot.

But other than rising phenom George Lombard Jr. at shortstop, the rest of the infield is murky. Ryan McMahon is a great glove at third, but is overpaid and a black hole of a bat. Don’t be shocked if the Yankees eat $16 million and DFA him.

That leaves gaping holes at both second and third base, so who steps in? Jose Caballero can play both positions and is competent enough with the glove. Maybe Anthony Volpe comes back to play second against lefties. Free agent and former (Phormer?) Phillie Alec Bohm isn’t much with the glove or bat, but still hit .298 in the second half.

So, what does that mean when there’s a clear need on the roster and no easy quick fix? Look for Cashman to play the trade game here.

Outfield

Contrastingly, this is where life gets easier for Cashman. The clear move here is let Trent Grisham walk, and roll with an outfield of Cody Bellinger, Spencer Jones, and Aaron Judge. That leaves Ramos as a platoon bat, but the Yankees still need a proper fourth outfielder. Paging Jasson Dominguez, perhaps? Again? And maybe for real this time?

There is also the looming Giancarlo Stanton question. He’s due $15 million next year, the last one guaranteed on his contract, and about to turn 37 next month. Could the Yankees trade him? Buy him out? Simply release him and send him home with a handshake? The Yankees can’t really afford to bank on his health anymore.

This could mean yet another trade opportunity for Cashman, but for whom remains unclear. This could also be an opportunity to sign super-utility man Mauricio Dubón in free agency.

Starting rotation

Four words for a pitching staff whose 3.23 ERA ranked tops in the majors: Leave well enough alone. The Yankees’ rotation isn’t immune to injury, but set in stone for next season. Likely Cy Young winner Cam Schlittler will lead the pack. Followed by veterans Gerrit Cole, Max Fried, Carlos Rodon, and one of Will Warren or Ryan Weathers? And now add Clarke Schmidt back from Tommy John along with pitching depth/development that is every organization’s dream?

Cashman has options to build his entire staff from within, rotation to bullpen, or he can trade some of it away for bullpen or batting help.