bleacherreport
Seventeen years have passed since the New York Yankees last hoisted the World Series trophy. For over a decade and a half, the team has flirted with championship greatness only to fall short. If this were an elaborate prank orchestrated by owner Hal Steinbrenner, general manager Brian Cashman, and manager Aaron Boone, the dedication would be almost commendable. But Yankees fans are not amused—far from it.
The reaction from the Yankee Stadium crowd after the team was swept out of the 2026 playoffs by the Tampa Bay Rays on Wednesday spoke volumes. When Trent Grisham struck out with the tying run in scoring position, there were no collective groans followed by pained silence. Instead, loud, unmistakable boos rained down. A fanbase doesn't resort to boos in such a moment if the outcome is truly shocking—or if the journey to that point was enjoyable. Such boos only occur when the jig is up, especially when that exact moment of defeat has become an annual tradition. The Yankees keep selling false hope, and fans are tired of buying in only to be conned. Those boos say, "Not this crap again." They want 27 World Series titles to become 28. 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? Congratulations! Nobody cares. It's about championships, and labeling Yankees fans as spoiled for such high expectations misses the mark. They're not blind to the team's history, nor to the fact that the Yankees remain a business behemoth. According to Forbes, the franchise is worth $8.5 billion and generated $710 million in revenue last year. There's no excuse for this team not to be consistently at the top of the baseball world. The fact that they've done so just once in 25 years inevitably makes one wonder, "Who the hell is running this place, anyway?"
Defenders of Cashman and Boone exist. Boone's 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 and 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. 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 maintaining 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.
Originally reported by bleacherreport.