3 Things Brian Cashman Must Do Differently in 2027 After Getting Contract Extension

Brian Cashman is inevitable. After his 29th season as general manager of the New York Yankees, Cashman will return for a 30th season after agreeing to a contract extension (h/t Talkin' Yanks).

However, this decision will undoubtedly draw divided reactions from Yankees fans, as Cashman has been unable to lead New York to a World Series title in 17 years. Those last 17 years have seen mixed results in both internal player development and external acquisitions, despite the Bronx Bombers consistently finishing with winning records.

It's likely Cashman got the extension because of the emergence of a new homegrown nucleus, which consists of Ben Rice, Cam Schlittler, and George Lombard Jr. Cashman deserves credit for already bridging the gap between the Aaron Judge era and the next face of the franchise. But at the same time, the Yankees need to capitalize on the Judge window with a ring.

But to win a championship with both the old and new guard, Cashman needs to improve in these three areas.

1. Addressing all roster needs

One of Cashman's worst habits in recent years is his tendency to ignore certain areas of weakness on the Yankees' roster.

Third base was a notable example for years. After trading Gio Urshela for the immensely disappointing Josh Donaldson, the Yankees went with patchwork options like Oswaldo Cabrera, Jon Berti, and Oswald Peraza for the first half of 2024 before acquiring Jazz Chisholm Jr. (a natural second baseman) at the trade deadline to play the position.

In 2025, Peraza and Cabrera ineffectively held the role until the Ryan McMahon trade. This ended up being even worse than the Donaldson trade.

Another example last season was Cashman's failure to provide greater bullpen depth. After an active 2025 trade deadline that saw the Yankees get multiple relievers, he ignored bullpen upgrades during the winter despite losing both Devin Williams and Luke Weaver.

At the 2026 trade deadline, he traded away Yovanny Cruz, Jake Bird, and Camilo Doval. Granted, many of those relievers struggled, but Cashman couldn't make them "addition by subtraction" with proper replacements.

The most egregious example was in 2019, when Cashman did very little to improve the starting rotation. The only starter he added during the winter was James Paxton, and he failed to trade for a starter at the deadline despite Luis Severino missing the vast majority of that season. The 2019 Yankees were arguably the best team of the Judge era, and while the lineup went cold in the ALCS, they didn't have the starting pitching necessary to beat the Astros that year.

Most teams that eliminated the Yankees in the postseason throughout the Judge era were strong at all positions, while the Yankees still had clear weak points. Cashman cannot let this happen anymore and needs to treat every position on the roster with urgency.

2. Be more open to change

Speaking of urgency, Cashman has a habit of committing too long to certain players. This can applyto Aaron Boone, but even when someone is clearly struggling, Cashman stubbornly sticks to the process and banks on results evening out.

Perhaps the most notable example is how Cashman handled Anthony Volpe. He was so quick to label him as the Yankees' shortstop of the future that he ignored stars like Corey Seager, Marcus Semien, and Carlos Correa in free agency in 2021-22, and Trea Turner, Dansby Swanson, and Correa again in 2022-23.

Fast forward to 2026, and George Lombard Jr. is now the shortstop of the future, while Volpe is looking for both a new position and offensive consistency.

Other examples include internal roster options. Because Cashman traded for Isiah Kiner-Falefa as part of the Donaldson deal, he started at shortstop for almost the entire 2022 season; even when he struggled offensively and defensively, using Oswald Peraza was rarely considered.

In 2024, Cashman traded for the struggling Alex Verdugo, who declined rapidly after June but still played every day while Trent Grisham rode the bench (this was a year before Grisham's breakout).

This season, Ryan McMahon had two trips to the IL on top of his all-around struggles, yet he instantly got the starting third base job back upon returning. That said, having a $16 million player on the bench isn't a good look for Cashman, and he knows that.

The collective trio of Hal Steinbrenner, Cashman, and Boone hasn't always chosen the right players, whether in terms of playing time, trades, or contracts. This leads to Cashman's worst trait, which he desperately needs to fix.

3. Take accountability for roster mistakes/team failures

This flaw reared its ugly head again on Wednesday, although it came from Steinbrenner rather than Cashman himself. Steinbrenner solely blamed the players for coming up short in the postseason this year, while complimenting Cashman for building a "World Championship-caliber team".

On the one hand, Steinbrenner isn't wrong about the players: they collectively underperformed in the ALDS. But on the other, Cashman has not built the best team possible, and he needs to own up to that.

The aforementioned Donaldson and McMahon trades were huge mistakes. Committing to Volpe without even considering external options was a huge mistake. Leaking Aaron Judge's proposed extension was a mistake that almost cost the Yankees the face of their franchise. Those are squarely on Cashman.

There's also extending Aaron Hicks instead of pursuing Bryce Harper and/or Manny Machado in 2018-19. Adding an extra year to DJ LeMahieu's deal upon re-signing him for a lower AAV backfired and resulted in more dead money.

The Yankees stuck with Anthony Rizzo instead of trading for Matt Olson or signing Freddie Freeman. Ryan Weathers was the only offseason addition in 2025-26. All of these transactions can be blamed primarily on Steinbrenner. But Cashman still deserves blame for getting the wrong players or putting the Yankees in a difficult position to make upgrades.

Even with all the talent on the roster, the Yankees only look like a World Series-caliber team when Aaron Judge is on the field.

When he wasn't on the field in 2023, the Yankees almost finished with a losing record. This year saw a playoff appearance but an ALDS sweep without the Yankee captain. If Cashman really built a World Series-caliber roster, they could make a deep playoff run without Judge and possibly win multiple titles with him.

Yes, the players need to collectively step up. But Cashman has to recognize that the rosters he's built in the Judge era haven't been good enough. So he needs to hold himself accountable and learn from those past mistakes.

If Cashman recognizes where he can do a better job and build the best roster possible, then he'll prove to the Yankees that his recent extension was warranted.

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