ESPN's offseason forecast for Yankees makes 2024 World Series failure worse

New York Yankees fans who are expecting a big offseason from general manager Brian Cashman are in for a rude awakening. Even if Cashman were interested in pushing more of his chips to the center of the table this winter (there’s no indication that he is), he’d be staring at a weak free agent market. The trade market looks similarly barren. 

Sadly, the Yankees will have a tough time dramatically improving their roster in the coming months, which will only serve as a painful reminder that Cashman should have been more aggressive in 2024.

Grim offseason forecast makes the Yankees’ front office look even sillier for not taking 2024 by the horns

While the 2025-26 offseason might feature a blockbuster surprise or two across Major League Baseball, the buyer’s landscape is looking mediocre at best. Unless you’re a believer that Cashman can miraculously pull off a deal for Tarik Skubal (if Skubal even hits the trade market, to begin with), the only superstar set to become available for New York is Kyle Tucker, who could actually be a key pickup for the Yanks, especially if they end up losing both Cody Bellinger and Trent Grisham.

ESPN’s David Schoenfield recently touched on this while writing about the Yankees’ offseason outlook. 

“Outside of Kyle Tucker, the rest of the outfield free agent class is pretty thin … so the Yankees will have competition for Bellinger's services,” Schoenfield wrote, before speculating that New York could turn to prospect Spencer Jones to fill an outfield vacancy.

“The other option is to hand center field to Spencer Jones, the 6-foot-7 slugger who hit 35 home runs between Double-A and Triple-A,” Schoenfield wrote. “Although he also struck out 179 times in 116 games, he leaves a lot of questions as to how the bat will translate to the majors. Despite his size, he's a good athlete (he also swiped 29 bases) with the instincts to remain in center field.”

Yikes. So an outfield that featured Aaron Judge and Juan Soto in 2024 could by 2026 feature Judge, an unproven prospect, and possibly another question mark? That sounds like a franchise moving away from contention, not towards it.

The Yankees didn't capitalize on their big opportunity in 2024

Speaking of 2024, it’s becoming clearer with each passing day that the Yankees missed a huge opportunity that season. Yes, the Yanks obviously reached the World Series, but they would have had a much better chance of taking home the title had the front office been more aggressive during the two transaction cycles that preceded the Fall Classic, especially when you consider that the Los Angeles Dodgers took on the exact, aggressive mindset that the Yankees lacked.

There were multiple occasions where Cashman dropped the ball. For whatever reason, he reportedly refused to increase his initial offer to Blake Snell in the 2024 offseason, leading Snell to sign a one-year deal with the San Francisco Giants (Cashman failed to snag Snell again in 2025, but that’s another story).

The Yankees ended up with Carlos Rodón, a far inferior option. With all due respect to Rodon, who was excellent in the 2025 regular season, he’s never delivered in a big way in the postseason, which is what the Yankees should be looking for.

The 2024 trade deadline wasn’t a big success for Cashman, either. He did snag Jazz Chisholm Jr., but the bullpen and defensive issues remained unsolved, and Alex Verdugo, for some reason, remained on the team.

Had the Yankees been more aggressive in the 2024 offseason and at the trade deadline, they would have given themselves a better shot to take down the Dodgers in October. And it was of paramount importance to do so because that looks like it may have been among the best opportunities the Yankees had at a title — or will have — in the 2020s (a.k.a. Judge's prime). 

Cashman didn’t seize the moment. He had lightning in a bottle with Judge and Soto in the same lineup, not to mention a healthy Gerrit Cole headlining a very solid rotation. By the very next season, Soto and Cole were both out of the picture. Cole's injury can't be attributed to Cashman, but it's just another example of how quickly fortunes change, and how when you have a special (and healthy) season brewing, you need to pounce.

Cashman's been managing the Yankees' roster as if getting in the playoffs each year is the main goal (and he’s hit that mark nearly every season), but he hasn’t shown the awareness to go absolutely all-in at the right moment, like the Texas Rangers did in 2023.

Sustainable success is a noble blueprint, but Yankees fans at this point would trade one title for a down year or two. Besides, “sustainable success” in the Bronx has always meant championships, and nothing short of it.