Grading the Yankees’ calculated ‘run it back’ offseason strategy so far

The 2026 offseason has been, by all accounts, a snooze fest for the New York Yankees. If you were refreshing Twitter waiting for a blockbuster trade or a shock signing, you probably ended up with nothing but a thumb cramp.

General Manager Brian Cashman decided to largely sit out the madness, opting instead to double down on the roster he assembled last summer. To the casual observer, it looks like laziness. But from inside the front office, the perspective is entirely different: they believe they just acquired a “new” team by retaining the pieces they only got to test drive for two months last year. Gary Phillips of the New York Daily News suggested as much on the Fireside Yankees podcast.

Cashman is banking on the idea that a full season of his 2025 trade deadline acquisitions—plus the internal rise of some elite youth—is worth more than any external splash. It’s a gamble, but when you break down the “new” faces who are actually returning faces, the logic starts to make sense.

Jose Caballero: The Speed Demon Unleashed

If there is one player who transforms this roster with a full 162-game workload, it’s Jose Caballero. The Yankees acquired him from the Rays at the deadline, and he didn’t just fit in; he exploded. In his short 40-game stint in pinstripes, he slashed .266/.372/.456, posting a remarkable 134 wRC+ that made him significantly better than the league average hitter.

But the real weapon is his legs. Caballero swiped 15 bases in New York alone, finishing the year with 49 steals total. We finally have a guy who can manufacture runs at the bottom of the order. Cashman isn’t looking for a shortstop; he believes he already has an elite utility weapon who can change games with his 90th percentile Range and chaos on the basepaths.

Amed Rosario: The Lefty-Mashing Insurance Policy

Bringing back Amed Rosario on a one-year, $2.5 million deal was the most “boring” smart move of the winter. We saw glimpses of it last year, but Rosario’s value is specific and elite: he destroys left-handed pitching. In 2025, he hit .302 with an .819 OPS against southpaws. With a lineup that can get lefty-heavy, having Rosario available for a full season to platoon at third, second, or the outfield prevents the offense from stalling out against tough lefties.

Jake Bird: The High-Upside Project

This is where Matt Blake earns his paycheck. Jake Bird’s Yankees tenure began with a horrific 27.00 ERA in three appearances, a number so bad it’s almost funny. But the front office is ignoring the surface stats and looking at the “shapes.” Bird possesses a sweeper that held hitters to a .257 average (not great, to be honest) and elite movement that simply needs to be harnessed within the zone. A full offseason in the Yankees’ pitching lab could turn him from a deadline bust into a legitimate high-leverage arm.

The “New” Old Guard and the Youth Movement

The retention of Cody Bellinger (five years, $162.5 million) and Trent Grisham ($22 million QO) ensures the outfield defense remains elite. Bellinger’s 29 homers and .272 average are irreplaceable, and Grisham’s 34-homer power provides instant offense, even if it comes with a low average.

But the X-factor is Cam Schlittler. The rookie isn’t a trade acquisition, but after debuting last year with a dazzling 2.96 ERA and 84 strikeouts in 14 starts, he enters 2026 as a legitimate rotation piece. Getting a full season of his “ace upside” is effectively like trading for a frontline starter.

The Final Grade: B

I can’t give this offseason an “A” because the rotation is still held together by surgical tape and hope. However, retaining Bellinger and Grisham while getting full seasons from Caballero and Schlittler raises the team’s floor immensely. It wasn’t sexy, but it was solid. Cashman didn’t win the winter, but he made sure he didn’t lose the summer.