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Hal Steinbrenner Needs to Join Yankees Post-Season Presser
Dec 21, 2022; Bronx, New York, USA; Hal Steinbrenner during a press conference at Yankee Stadium. Mandatory Credit: Jessica Alcheh-Imagn Images Jessica Alcheh-Imagn Images

The New York Yankees last won a World Series in 2009. Hal Steinbrenner was on the field for that. In 2024, when Major League Baseball set the stage on the field after they defeated the Cleveland Guardians, Steinbrenner managed to show up then, too.

If the organization finally captures that 28th championship, which has eluded them for the better part of two decades, you can expect the son of beloved owner George Steinbrenner to be there, holding the trophy proudly and most likely having a word for his detractors. Whether that day comes or not remains to be seen, but until then, fans and media alike can just expect Steinbrenner to be an absentee owner.

What Fans and Media Will Get

For now, everyone will have to settle for his two capos, Brian Cashman and Aaron Boone. This week, the general manager and his manager will make their first appearances since their team was ousted by the now lifeless Toronto Blue Jays without their boss.

They will answer questions from the press about what went wrong. The inquiries hurled at them will surely be about their previous denials that shortstop Anthony Volpe needed surgery, surface-level coaching changes, and just how it felt to see another team from the American League East play New York, New York, in their own stadium.

While these questions are not without merit, the answers will ring hollow. Boone and Cashman have done this after every playoff loss. Cashman, himself, has been front and center for these occasions even longer.

Yet, the longer the organization goes without a championship, despite promises that this will be the year every Spring Training, because it's "championship or bust" when the pinstripes take the field, the less everyone sees Steinbrenner.

Last Appearance

The owner's last public appearance was when the team decided to disband the controversial facial hair policy. Before then, he made comments that it was hard to keep up with the Los Angeles Dodgers. This came after the team that ousted them from the World Series mocked his organization relentlessly in the off-season.

Steinbrenner is an apparition at this point. He wasn't there when the team honored CC Sabathia, who delivered his most recent championship to him. Steinbrenner will gladly cash in on this every time the organization decides it's time to capitalize on nostalgia, though.

While it is true that Steinbrenner has ponied up enough for the Yankees to be one of the top spenders in terms of active payroll every year, the flaws on the field are still glaring. In back-to-back seasons, defensive lapses seem to have put the death knell on their year, with the fifth inning of game five now living in eternity.

Jessica Alcheh-Imagn Images

It's Time for Steinbrenner to Answer

The questions of what went wrong will be thrown at Cashman later this week, but Steinbrenner won't be around to ask why he keeps trotting out the same front office year after year, with the finish to each season being more disappointing than the last. If there is one person who can make any genuine change, it's him, but it seems the owner is always on the sidelines, taking out his checkbook every now and then, even though it feels predictable at this point that the organization will not live up to its "championship or bust" moniker when the games matter most.

To be successful, George's son doesn't need to wake up one day and suddenly become his dad. It's not in his nature to be that, and he shouldn't be. Being a nostalgia act hasn't worked for the Yankees on the field, and it won't work for the man running the team either.

Instead, Steinbrenner needs to ask himself two questions. The first is why his team is tops in payroll every year, despite the season ending the same way every year. The second is, who can be put in charge of his team to do that?

If these questions are not important to him, then it would be better if Steinbrenner found a podium and admitted that his World Series is getting five postseason gates in 2025. The idea that the Yankees are thirsting for that 28th championship once pitchers and catchers report feels like a stock answer.

It would be more believable if Boone whipped out a spreadsheet, pointed to the tickets sold the previous season, and said that's what they hope to surpass. They can have "New York or Nowhere" sponsor one of their $400 jackets from the team store on the spreadsheet.

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This article first appeared on New York Yankees on SI and was syndicated with permission.

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