The Yankees are bringing Aaron Boone back for 2027. I’m fine with that. The Yankees really need to look at Brian Cashman, and his contract runs out this winter.
I’m a die-hard Yankees fan, and watching Tampa Bay sweep us out of the ALDS and then march into the World Series hurt. When I look for who to blame, I don’t look at the dugout. I look upstairs.
🎯 Key Takeaways
- Boone stays: Aaron Boone returns for 2027, the final year of his contract and his 10th season.
- Cashman’s deal expires: Brian Cashman has run the Yankees since 1998, and his contract is up this winter.
- The needs went unmet: Third base, shortstop and catcher were holes, and the front office never fixed them.
- Our take: Keep Boone. Seriously consider moving on from Cashman.
Table of Contents
Why Keeping Aaron Boone Is the Right Call
The Yankees confirmed Boone will return for the final year of his deal, according to multiple reports summarized by amNY. He has made the postseason in eight of his nine seasons and has one pennant. He has no championship.
Here’s why I think it’s the move. With a lockout looming when the labor deal expires on December 1, teams can’t talk to players during a work stoppage. This is not the winter to blow up your coaching staff unless your manager is doing a bad job, and Boone wasn’t.
He kept this team competitive and in the playoffs without its best player. Aaron Judge missed much of the season and the entire postseason with injuries. That’s not a small thing.
That said, Boone has to win now. Going into a 10th season, the clock is loud. The Yankees haven’t won the World Series in 17 years, which ties the longest drought in franchise history since their first title in 1923.
Brian Cashman Is the Real Problem
“If I’m going to blame anybody for the shortcomings of the Yankees this year, it is Brian Cashman. I’d keep Boone. I’d fire Cashman.”
Dave Simon, Tremendous Sports Talk, October 20, 2026
Cashman has been the general manager since 1998. Ownership hasn’t signaled it wants a change, per reporting via Yahoo Sports, and he’ll likely be back. I’m not sure he should be.
He disappointed me in the offseason and at the trade deadline. This is now a couple of offseasons and a couple of deadlines in a row where the obvious needs didn’t get addressed. Third base. Shortstop. Catcher. Time and time again, nothing.
The ALDS showed it. The Yankees struck out 31 times and managed 12 hits in three games, the fewest in a multi-game postseason series in franchise history, according to Yahoo Sports. Cody Bellinger went 1-for-12. Without Judge, no one could carry it.
The Munetaka Murakami Question
This is what gets me. A Japanese slugger on the market plays third base: Munetaka Murakami. He went to the White Sox, and the Yankees showed no interest.
Are you telling me you’d rather have Ryan McMahon at third base than Murakami? McMahon is owed $16 million next season. Murakami can hit home runs, and he helped turn the White Sox from one of the worst teams ever into a playoff team this year. They won their Wild Card series against Houston before Cleveland knocked them out.
What do I know? I’m just a fan. He’s Brian Cashman. But it’s 2026, baseball is changing, and you need somebody who can make a deal and get you a third baseman.
Are the Yankees Hungry Enough?
One of my co-hosts raised a fair point on the show. The Yankees have a ballooning payroll tied up in a handful of stars. The question is simple: are those guys hungry?
I think they are. Judge wants to win. After the series, he said ownership and the front office “should go all-in.” The pitching staff performed the way it had all season. The arms weren’t the problem. Bellinger was the one real disappointment among the big contracts, and Judge simply wasn’t on the field.
That’s the thing. Hunger isn’t the issue. Roster construction is. And roster construction is the general manager’s job.
What the Yankees Should Do This Winter
My prediction: Steinbrenner keeps Cashman, because that’s what he does. If I’m making the call, I roll the dice on a new GM and see what he or she can do. At minimum, the Yankees need to land a real third baseman and settle shortstop before the lockout freezes everything.
Could I be wrong? Sure. Cashman has built winners before, and a new front office can make things worse. But watching two small-payroll teams in the Rays vs Brewers World Series tells you money alone doesn’t do it. Building the roster right does.
Reality Check: The Yankees Don’t Fire GMs
The Reality: Cashman has outlasted managers, owners’ moods and almost three decades of criticism. He’ll probably sign again. That’s exactly why Boone is the one feeling the heat in 2027, even though the holes on this roster were built in the front office.
We break down baseball every second Tuesday on Tremendous Sports Talk. For another manager on thin ice this winter, read our case on John Schneider and the Blue Jays.
Brian Cashman and the Yankees: Frequently Asked Questions
Is Aaron Boone returning as Yankees manager in 2027?
Yes. Aaron Boone returns for 2027, the final year of his contract and his 10th season as Yankees manager.
When does Brian Cashman’s contract expire?
Brian Cashman’s contract as Yankees general manager expires this winter. He has held the job since 1998, and ownership has not signaled it wants a change.
Who eliminated the Yankees in the 2026 playoffs?
The Tampa Bay Rays swept the Yankees 3-0 in the ALDS, then won the AL pennant.
Why did the Yankees pass on Munetaka Murakami?
The Yankees showed no interest in Murakami, who signed with the White Sox and helped them reach the playoffs. Dave Simon calls it one of Brian Cashman’s biggest misses.
