When the Yankees entered the regular season, I saw it as improbable for the team to win 94 games or the pennant since Gerrit Cole was hurt.

This team showed a lot of good; they found offense after losing Juan Soto and developed young unproven players into key parts of the roster.

Aaron Judge continued to be the best player on the planet, and Giancarlo Stanton posted his most WAR in a season since 2021.

Since it’s New York, the good that comes from that will be vanquished over the next few weeks as the weight of a disappointing ALDS exit.

Brian Cashman will need to do something dramatic to pick up the pieces from the 2025 season and assemble a squad capable of finally getting over the hump in 2026.

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Disappointment fueled the Los Angeles Dodgers, one-and-done playoff appearances in 2022 and 2023 where they went a combined 1-6 would set the stage for one of the biggest offseasons ever.

Signing Shohei Ohtani to a $700 million deal would be enough to sell fans that the organization is tired of losing in the postseason, but they went above and beyond.

A record-breaking $325 million deal for Yoshinobu Yamamoto and a $23.5 million for Teoscar Hernandez while also trading for Tyler Glasnow, helping them win the 2024 World Series.

The Yankees watched them pop champagne in the Bronx after Game 5 of the World Series, and then they watched the Mets outbid them to land Juan Soto.

Yamamoto was also a player whom the Dodgers outbid the Yankees for, although I don’t know how serious he was about going to the Yankees or Mets after Shohei Ohtani landed in LA.

With Kyle Tucker available this postseason and both Trent Grisham and Cody Bellinger hitting free agency, Hal Steinbrenner needs to bring in the top free agent to bolster the middle of the offense.

MLB: Chicago Cubs at New York Yankees
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Cody Bellinger should remain a ~3 WAR player with his elite defense and strong bat, but he is unlikely to replicate the 4.9 WAR and 29 home runs he put up in 2025.

The Yankees can’t expect to bring him back and get the same production in LF, but they can expect for Kyle Tucker to either match or surpass Bellinger’s production from 2025.

Jasson Dominguez in centerfield isn’t great, but Cody Bellinger did grade out as a -3 DRS and -1 OAA defender in centerfield this year so he wouldn’t be great there either.

Hal Steinbrenner will be told by Brian Cashman that the Yankees have an outfield issue and need to spend money to fix it, and if he is the owner this organization needs, he will tell the long-time GM that Kyle Tucker is on the table.

Failing most constitute change; the Yankees cannot tell themselves that signing Cody Bellinger over Kyle Tucker will fix any of their issues, it would almost guarantee that their outfield will be worse than it was in 2025.

Bellinger is likely to get a deal around $30 million AAV, while Kyle Tucker should sign a deal matching Aaron Judge in AAV (~$40 million), what player will Brian Cashman sign at $10 million that will make up that gap in value?

The Yankees competed with the Dodgers for Yoshinobu Yamamoto and lost, then competed with the Mets for Juan Soto and lost.

Star power is what separated you in 2024 from the rest of the American League, but in a world without Soto, teams like the Blue Jays had more than enough to handle you.

I know Kyle Tucker has historically not been a good playoff performer, but Aaron Judge and Giancarlo Stanton playing reverse roles this postseason should tell you how unreliable previous playoff production is for projections.

Aaron Judge, MLB: New York Yankees at Minnesota Twins
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As for pitching, the Yankees have five starters they can roll with in 2026 and project to finish inside the top 10 in rotation WAR and ERA with.

Gerrit Cole and Clarke Schmidt should return during the middle of the season, with arms like Elmer Rodriguez-Cruz, Ben Hess, and Carlos Lagrange having a chance to debut next year as well.

Adding a depth starter wouldn’t hurt, but the Yankees’ financial invesment needs to occur in the bullpen, where they’ll see Devin Williams and Luke Weaver hit free agency.

I hope we can see Williams return; he is one of the best relievers in the game and the team could have a dynamic backend duo with him and David Bednar that would terrorize the league.

Fernando Cruz, Camilo Doval, and Tim Hill are good options, but pushing each of those guys one spot further on the trust tree makes you feel a lot better.

MLB: New York Mets at New York Yankees, devin williams
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Jake Bird and Brent Headrick will be fun depth options that could have strong 2026 campaigns due to their high strikeout rates, and I could see a winter trade for bullpen support.

I don’t look at the 2025 Yankees as a collossal failure, but rather another missed opportunity to win a World Series, as there were real positives that separate them from previous seasons.

The Yankees twice had to turn to their farm system for full-time starters, as Will Warren and Cam Schlittler combined to produce a 3.98 ERA, 3.96 FIP, and 3.4 fWAR in 47 starts.

Schlittler is the best pitching prospect they’ll have in this wave, but Elmer Rodriguez-Cruz, Ben Hess, and Carlos Lagrange are all prospects who are as good if not better than Warren was a prospect.

Ben Rice finished with the same wRC+ than Jose Ramirez and more home runs than Fernando Tatis Jr. while playing just 138 games, and Austin Wells finished 10th among catchers in fWAR this season.

MLB: Toronto Blue Jays at New York Yankees, austin wells
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Jasson Dominguez didn’t have a big year, but he looks like a capable hitter who is an excellent baserunner, I think he’ll start on the 2026 Yankees and be a solid player.

Anthony Volpe presents a massive question at shortstop that the organization didn’t think it would have this soon when they went into the 2025 season, as his glove needs to be elite to carry a firmly below-average bat.

I think he can rebound into being a glove-first shortstop, but fans will be all over him this winter after a horrendous third year in the Bronx.

The future isn’t dim in New York. The lights have yet to go out for this window and core. That being said, they need to have the biggest offseason for any contender seeing that they’ll have more money than the Mets or Dodgers.

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