Remember when the New York Yankees used to dominate MLB and had made getting to the World Series a common thing? One of the most important reasons for that type of dominance was not settling for 2nd best. That is the type of mentality George Steinbrenner had. But after Hal Steinbrenner took over, everything has changed, and every mistake seems to be taking center stage.

In a recent interview, Hal Steinbrenner talked about the feelings of players and coaches heading into the offseason. As reported by Bryan Hoch, “Hal Steinbrenner says that when he talks to coaches and players, they believe the Yankees must cut down on ‘mental mistakes – baserunning for sure, which is why we made a [coaching] change. That has been a thorn in our side most of the season this year.'”

When George Steinbrenner ran the New York Yankees, he spared no expense and made every decision with the express purpose of winning championships. In contrast, under Hal Steinbrenner, the club has adopted more measured spending and corporate-style decision-making, which reflects a slower pace of change and deeper structural shifts.

The fans feel it: there’s less of the visceral “boss” energy George brought and more of a boardroom tone in how the franchise now operates.

Hal recently acknowledged the Yankees made frequent baserunning and mental mistakes in 2025 and has changed the coaching staff in response. For example, in August, the club committed a baserunning blunder when Jazz Chisholm Jr. was doubled off first base after straying too far on a popup, directly costing an inning in a 2-0 loss.

Such errors underline the urgency of operational discipline, yet the franchise’s pivot came only now, after mistakes had mounted.

The timing matters: by the time Hal’s leadership addressed these issues, the impact of missed opportunities was already visible in the postseason outcome. The Yankees’ 94-win 2025 season ended in the Division Series, and the fans lived every misstep. If the club truly expects to contend, Hal’s organization must move faster and demand execution not simply in promise but in sharp, decisive action.

George Steinbrenner treated second place like failure and built a dynasty on uncomfortable urgency. Hal Steinbrenner treats urgency like a suggestion and waits until the damage becomes obvious. If Hal truly wants a George-level legacy, he must stop reacting late and start acting first.

As Hal Steinbrenner continues to justify mistakes, the Yankees continue to make them

Every time the Yankees promise they’ve learned their lesson, they somehow pull off another decision that makes everyone reach for the aspirin. Hal Steinbrenner keeps talking about “trusting the process,” but the only real process lately is explaining why nothing is working. And now, with the latest roster move, New York is acting like stability is the same thing as progress. We’ve seen this movie before, and it never ends well.

Brandon Tierney believes the Yankees miscalculated by keeping Grisham despite persistent offensive inconsistency concerns. He said, “The Yankees made a colossal mistake” while warning of a “terrible offseason”. Tierney referenced Grisham’s 34 home runs and 74 RBIs, contrasted with his .235 average.

The decision shapes a difficult offseason by limiting financial room for Cody Bellinger. Analysts note it also delays opportunities for Jasson Dominguez and Spencer Jones next season. Fans worry about Grisham posting minus11 Defensive Runs Saved and minus3 Fielding Run Value.

Hal Steinbrenner keeps preaching patience, yet the Yankees keep stacking reminders that patience is expensive. New York still talks about championships while building a roster that looks allergic to urgency. If this is the blueprint for 2025, Hal might want a sturdier excuse ready.