Yankees Legend Defends Hal Steinbrenner For Quiet Offseason

The New York Yankees have not made many big moves since the 2025 season concluded, but the World Series isn't won or lost in the offseason.

Jul 27, 2025; Cooperstown, NY, USA; Hall of Famer Derek Jeter is introduced during the Baseball Hall of Fame Induction Ceremony at the Clark Sports Center. Mandatory Credit: Gregory Fisher-Imagn Images | Gregory Fisher-Imagn Images

It has been a frustrating offseason for New York Yankees fans.

The ball club is continuously in the mix for blockbuster trades and big-time free agent signings, yet the biggest move the Yankees have made so far is bringing Cody Bellinger back on a five-year, $162.5 million deal.

However, the Bellinger signing means that the majority of the 2025 team that won 94 games and made the postseason is returning in 2026. There were some key departures in the bullpen with Devin Williams and Luke Weaver switching boroughs and signing with the New York Mets, but the roster is largely the same.

Center fielder Trent Grisham signed his $22.025 million qualifying offer, and the Yankees avoided arbitration by signing back Jazz Chisholm Jr., David Bednar, Camilo Doval, Anthony Volpe and Luis Gil.

Oct 5, 2025; Toronto, Ontario, CAN; New York Yankees left fielder Cody Bellinger (35) rounds the bases after hitting a home run in the sixth inning against the Toronto Blue Jays during game two of the ALDS round for the 2025 MLB playoffs at Rogers Centre. Mandatory Credit: Kevin Sousa-Imagn Images | Kevin Sousa-Imagn Images

Even still, it's hard not to feel like the Yankees are falling behind the Los Angeles Dodgers, who landed Edwin Diaz and Kyle Tucker, or the Mets, who traded for Freddy Peralta and signed Bo Bichette.

But Yankees legend Derek Jeter has a different perspective on this offseason and is defending owner Hal Steinbrenner.

"I'm sure Hal is frustrated as well," Jeter told Fox News Digital. "Hal’s been willing to go out and get players and put the Yankees in a position to win."

Jeter Defends Steinbrenner

To Jeter, the World Series isn't won in the offseason — it's won in the season's final months.

"It’s a long season. I used to say it when I played — and people got tired of me saying it — the best teams make it to the postseason, and the hottest team wins. Teams that get there, whoever’s hottest can win a World Series," Jeter said. "They had a successful regular season, didn’t end up how they wanted to, but I’m sure things change. Trade deadline, injuries, a lot of things happen. So they obviously like the position they’re in, and we’ll see what happens."

Yankees Derek Jeter and the rest of the New York Yankees thank their fans after the final game at Yankee Stadium Sept. 21, 2008. | Frank Becerra Jr./The Journal News / USA TODAY NETWORK via Imagn Images

As for the Yankees missing on top available talent, Jeter says that he understands the frustration — especially after getting trounced 3-1 by the Toronto Blue Jays in the Division Series last season — but it ultimately comes down to how the teams perform on the diamond.

"Yankee fans, they have high expectations. They’ve always had high expectations. For them, if you don’t win the World Series, it’s a failure. In that sense, I have the same mindset. So I get the frustration," Jeter said. "...But ultimately, you have to go out on the field and perform."

While the offseason is still important for acquiring talent, Jeter finished with a reminder that the July trade deadline can also make or break a season.

"It all comes down to the trade deadline," Jeter said. "Teams change dramatically at the trade deadline."

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