Yankees Rely on Five Question Marks in Offseason That Raises Eyebrows

With a quiet offseason and big bets on a handful of unproven or recovering players, the Yankees' 2026 outlook is drawing skepticism from analysts.

The Yankees didn’t make the loudest noise this offseason, but that doesn’t mean they’re not setting themselves up for a pivotal 2026 campaign. While teams like the Dodgers and Mets made splashy moves and the AL East saw aggressive maneuvering from the Blue Jays, Orioles, and Red Sox, the Yankees opted for a more restrained approach-bringing back familiar faces and betting big on internal growth.

Trent Grisham and Cody Bellinger are back in pinstripes, and the Yankees added lefty Ryan Weathers in a trade. Beyond that, the front office focused on depth-Brian Cashman opting for stability over splash. But that strategy comes with its own set of risks, especially when you look at just how much is riding on a handful of players.

Former MLB GM Jim Bowden gave New York a “C” grade for their offseason, pointing to five players the Yankees are counting on in a big way-some returning from injury, others still trying to find their major league footing.

Let’s start with the rotation. Gerrit Cole and Carlos Rodón are both expected to begin the season on the injured list, and their timelines for return remain uncertain.

These are two arms the Yankees need at full strength if they’re going to contend. When healthy, Cole is a Cy Young-caliber ace, and Rodón has the stuff to be a high-end No.

  1. But health has been elusive lately, and the Yankees are banking on both to bounce back and help anchor one of the league’s top rotations.

That’s a big ask, and the margin for error is razor-thin.

Then there’s Anthony Volpe. The 22-year-old shortstop showed flashes last season, but now the Yankees are hoping for more than just flashes-they need a breakout. Volpe is also working his way back from injury, and while the team has veterans like Judge and Bellinger to carry the load, a leap from Volpe could be the difference between a playoff berth and a serious World Series push.

Austin Wells and Ben Rice round out the five players Bowden spotlighted. Both are young, talented, and unproven at the big-league level.

The Yankees are hoping one-or ideally both-emerge as legitimate contributors this season. That’s a lot of hope being placed on two players who are still developing, especially in a market that doesn’t often allow time for growing pains.

The bottom line? The Yankees are walking a tightrope in 2026.

They’ve chosen continuity over chaos, internal growth over external spending. If Cole and Rodón return to form, if Volpe takes that next step, and if Wells and Rice rise to the occasion, this team could be dangerous.

But that’s a lot of "ifs" for a franchise with championship expectations.

It’s not that the Yankees can’t make it all work-it’s that everything they’re banking on has to hit just right. And in a division as competitive as the AL East, that’s a high-stakes gamble.