Now Is the Time For the New York Yankees to Burn It Down

It's been 17 years. A decade plus seven of the New York Yankees walking right up to the line of being a championship-caliber team and stopping right there.

If it's an elaborate Andy Kaufman-esque prank by Hal Steinbrenner, Brian Cashman and Aaron Boone, the commitment to the bit is almost impressive. Yet Yankees fans aren't laughing. Far from it, in fact.

The Yankee Stadium crowd's reaction says it all after the Yankees were swept out of the 2026 playoffs by the Tampa Bay Rays on Wednesday. When Trent Grisham struck out with the tying run in scoring position, there wasn't one of those collective groans, followed by pained silence. There were loud, unmistakable boos.

A fanbase doesn't revert to boos in that situation if the outcome is genuinely shocking. Or, at the very least, if the ride there was fun.

Boos like that happen only when the jig is up, especially when that exact moment of defeat has become an annual rite of passage. The Yankees keep selling their fans false hope, and they're clearly tired of buying in only to get conned. Those boos say, "Not this crap again."

They want 27 World Series titles to become 28. Maybe, just maybe , it's time for the organization to get the message.

What Brian Cashman and Aaron Boone Have Done to the Yankees

Huh? What's that? The Yankees have had 34 consecutive winning seasons? Cashman has been in the front office for all of them? Boone has been in the manager's chair for the last nine?

It's the championships, stupid, and any attempt to label Yankees fans as spoiled for such high expectations misses the mark. They're not blind to the team's history , nor are they blind to the fact that the Yankees remain a business behemoth. Per Forbes , it's an $8.5 billion franchise that raked in $710 million in revenue last year.

There's no excuse for this team not to be at the top of the baseball world with some consistency. The fact that they have done so just once in 25 years inevitably makes one look around and ask, "Who the hell is running this place, anyway?"

Defenders of Cashman and Boone are out there. Boone 's own players consistently praise him , with three-time MVP Aaron Judge generally serving as his strongest ally. At any time, a veritable army of reporters goes to bat for Cashman for all he's accomplished .

True, Boone is good with the media and an effective heat shield for his players. And true, Cashman probably doesn't get enough credit for his development wins . He's the guy who believed in Judge and Cam Schlittler, and who can pat himself on the back for Ben Rice, George Lombard Jr. and Spencer Jones.

Yet if they get to own the positives of the modern-day Yankees experience, they must also own the negatives.

For all the Yankees' excellence at hitting home runs ( Fact Check: True ) and blowing away opposing hitters ( Fact Check: True ), what has mattered more in recent Octobers is just how bad they are at playing the actual game of baseball. Their collective proneness to mental gaffes and physical comedy is what doomed them in the 2024 World Series. This year, they did the same in Game 2 of the ALDS .

Cashman and Boone's ongoing failure to fix the problem* is only becoming a more glaring failure. Whereas the Yankees' fondness for homers in whiffs feels coded to the late-2010s, the 2020s are different. The Rays and Milwaukee Brewers prove that a team doesn't need the Los Angeles Dodgers' resources to play an "all of the above" style of baseball that is as overwhelming as it is aesthetically pleasing.

* So much for that weird " audit " in 2023, am I right?

The stacked failures are compounded by what was wasted. Those include the prime years of Judge, who might be the greatest right-handed hitter ever. They also include Gerrit Cole's prime years, a Cy Young Award winner who'll end his career with a compelling Hall of Fame case.

At some point, shouldn't somebody have to pay for this?

What Hal Steinbrenner Has Done to the Yankees

The answer is yes. A hard yes. Steinbrenner should absolutely fire Cashman and Boone and look elsewhere for people who can turn fresh perspectives into a better path forward for the Yankees.

Easier said than done, to be sure, and the Yankees only need to look across town at the Mets to see that. They also have vast wealth, and they arguably have an even greater desire to win. Yet Steve Cohen has yet to crack the code, at least in part because David Stearns isn't all he was cracked up to be .

But then there are the Dodgers. Setting aside the very real questions about Mark Walter's business empire, they have long since usurped the Yankees as the model for what happens when great power meets great ingenuity. Andrew Friedman is astoundingly good at running the front office, while Dave Roberts is everything a modern manager should be. They are the anti-Cashman and anti-Boone.

The dream for the Yankees is getting their own pair. An executive as good as Friedman at maintaing a talent pipeline even without the benefit of high draft picks and large international bonus pools. A manager as good as Roberts at both communicating and working the Xs and Os. And between the two of them, a shared philosophy on playing holistic ball. Homers and strikeouts are nice. Homers and strikeouts plus good defense and baserunning is better.

Will Steinbrenner actually move on from Cashman or Boone? Eh, don't count on it.

Boone has another year on his contract. Cashman does not, but is expected to sign a new deal. With a lockout looming, any effort by Steinbrenner to burn it all down and start anew faces a major complication.

What Steinbrenner can do either way this offseason is engage in some soul-searching. Or, if he wants to listen to Judge, he can merely look around for his wallet:

Steinbrenner probably doesn't want to hear it, given how often he's complained about having to operate with such high payrolls. Yet every time he does, he insults his fanbase's intelligence.

Again, these are the literal Yankees we're talking about. Back in 2011, the Yankees' year-end $216 million payroll accounted for 49 percent of $439 million in revenue. Last year, they had a $301.5 million payroll against $710 million in revenue. That's 42 percent.

If Steinbrenner isn't going to can Cashman or Boone, the best possible version of the coming offseason is one where he finally channels his late father, leaves no stone unturned, and doesn't leave any check unsigned. Tarik Skubal? Randy Arozarena? Teruaki Soto? Screw it, let 'em all come down.

Even that would feel like a half measure, though. Even with esteemed new guests, it'll be the same party if Cashman and Boone are still hosting. When asked to attend, fans would have every right to spin one of Yogi Berra's greatest quotes.

Nobody goes there anymore. It's too depressing.