Running it back is the quickest way to second place.
The New York Yankees are entering this offseason with the clear understanding that the 2025 roster was good, but it wasn’t good enough to simply copy and paste into 2026.
General Manager Brian Cashman knows he has to make upgrades rather than just hoping for internal improvement. As we stare down the barrel of the winter meetings in December, the priority list in the Bronx is becoming crystal clear, and it starts with a massive vacancy in the outfield.
Finding a partner for the Captain
The outfield is priority number one for a reason. Cody Bellinger is sitting there in free agency, and the Yankees need to fill that spot immediately. It is becoming obvious that the front office isn’t overly excited about handing a starting job to Jasson Dominguez right now. Even top prospect Spencer Jones, who is knocking on the door of the MLB, is viewed as unproven and inexperienced. You cannot trust a championship chase to rookies who haven’t played a lick of big-league ball.
This brings us to the expensive decision. Extending Bellinger feels like the easy call. He is the better defensive piece, and his swing is tailor-made for the short porch at Yankee Stadium. However, his market is heating up. Then you have the big fish in Kyle Tucker. Tucker is two years younger and offers the kind of electric offensive consistency that Bellinger sometimes lacks. He would be a true partner for Aaron Judge, capable of carrying the lineup on his own.
Tucker will likely cost double what Bellinger commands, so the Yankees have to decide if they want to spread the wealth or go all-in on a superstar duo. They will likely land one of them, which probably forces a position battle between Dominguez and Jones for the fourth outfield spot or leads to a trade.
Rebuilding the bridge to the ninth
The bullpen situation is equally fluid. The Yankees made aggressive moves at the deadline last year to bring in David Bednar, Camilo Doval, and Jake Bird. Those three are expected to play huge roles in 2026, but the unit is currently down Devin Williams and Luke Weaver. You cannot lose two high-leverage arms and expect the late innings to go smoothly.
Bringing back Weaver makes a lot of sense. Despite a down season where he posted a 3.62 ERA and struggled with home runs, the team still likes him. He would be an affordable option to stabilize the middle innings. If they don’t reunite with Weaver, Cashman will likely look to the trade market to find a cheaper asset, but ignoring the bullpen is not an option.
The uncomfortable truth at shortstop
Some people might look at the infield and see stability, but the New York Yankees should see a flashing warning light. We need to prepare for the reality that Anthony Volpe might not be an above-average player in 2026. The 24-year-old is entering his fourth season, and he has been well below average offensively for three straight years. That is a large sample size.
READ MORE: The Yankees already have their shortstop competition on the roster
Defensively, he is usually a Gold Glove caliber asset, but a partially torn labrum last season ruined his metrics. That injury is expected to keep him out for the first few weeks of the regular season, forcing the team to turn to Jose Caballero to fill the gap. Volpe has produced more like a backup utility man than an everyday starter recently.
The front office will likely give him one more year to prove he belongs before making a drastic change, especially since top prospect George Lombard Jr. likely needs one more year in the minors. However, the clock is officially ticking. The Yankees cannot wait forever for the bat to wake up. They have to upgrade the roster this winter, and that means taking a hard look at every single position that isn’t pulling its weight.
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