The Bronx Bombers have now gone 16 years without October glory. When the Yankees fell to the Blue Jays in Game 4 of the 2025 ALDS, the loss carried a familiar sting—another season ending too soon, another round of questions about why this team can’t get over the hump. In the aftermath, focus is shifting to decision-makers off the field. Owner Hal Steinbrenner and general manager Brian Cashman are under scrutiny for their continued support of shortstop Anthony Volpe, despite growing defensive concerns.

That stance has put the Yankees in an increasingly difficult position, and it somewhat contributed to the loss. An MLB scout didn’t mince words when evaluating the situation, stating: “The Yankees were burned on most of his errors this season, especially late in the game. Caballero is a better player in all areas of the game besides power, but they aren’t going to use him like that.” The assessment was clear—there’s a better defensive option available, but the clubhouse didn’t initiate the switch when it mattered most.

Christian, co-host of a Yankees podcast, bluntly expressed how the crucial decision was given to the GM and the skipper. He wrote on X: “Hal Steinbrenner spent $300M on the #Yankees payroll this season. That’s not my problem. That’s never been my problem with Hal. My problem is that he’s turned the keys over to Brian Cashman and it hasn’t worked. Aaron Boone as manager hasn’t worked. Hal is the one guy who can change all of this, and he doesn’t. That’s my problem with Hal Steinbrenner.”

The Yankees’ leadership is uncomfortable, as it’s clear that GM Brian Cashman and manager Aaron Boone have supported Anthony Volpe despite his notable defensive struggles. Volpe committed 17 errors in 2025, drawing significant attention due to the importance of his position. Nevertheless, the front office’s message remains unchanged: trust the process and believe in the player.

The contrast with Hal’s father becomes more glaring with each passing October. Hal’s father, George Steinbrenner, known as “the Boss” for holding people accountable, making adjustments when things didn’t go as planned, and expecting the best from everyone. He controlled the team from 1973 until he died in 2010. George’s approach produced seven World Series titles during his tenure. But under his son’s tenure, the franchise has won only one pennant in 15 years.

All threads converge at a single point: in a season where consistency separates contenders from pretenders, the decision to support Volpe despite his mistakes became controversial. Cashman and Boone supported Volpe through his struggles, while Hal’s lack of involvement made him seem like an absentee leader, unlike his father, George.

The Yankees’ troubles in 2025 go beyond Volpe’s errors; they highlight a lack of accountability. Hal’s willingness to spend did not equate to oversight, and by handing control to Cashman and Boone, he surrendered accountability. Now, the absence of Steinbrenner’s guiding influence is more apparent than ever. With the season getting over in yet another disappointing manner, one question looms: what’s next for the Bronx Bombers?

Rebuilding the Pinstripes: What must change for the Yankees to return stronger

The path forward demands more than roster tweaks. Hal Steinbrenner must examine every aspect of the team. Reports suggest there are questions that the front office must answer before entering the 2026 summer.

On the surface, the roster needs are obvious. What used to be a strength for the Yankees has become a weakness. This year’s relievers let them down at key times, costing them the AL East and important games in October. The Yankees bullpen ranked 23rd in the league with an ERA of 4.37 and a WHIP of 1.316.

Beyond the pitching staff, the outfield picture needs clarity.

Judge is back, and Dominguez is still in charge, but Bellinger and Grisham might quit. The team has to choose between re-signing veterans, promoting prospects, or making a trade. Spencer Jones is a possible choice, but his high strikeout rate raises some worry.

Third, the voices are still asking questions about leadership and direction. Cashman’s long time with the team, Boone’s contract security, and the team’s need for stability. But the idea that the manager or front office could change is still on the table after another early exit in October.

While some roster changes are likely, they might not be enough. The Yankees’ owner, GM, and manager will need to take aggressive action, not sit back and wait, if they want to make real improvements.