Yankees Captain's Biographer Doubts Hal Steinbrenner’s Passion to Win

Originally posted on Athlon Sports | By Kristie Ackert | Last updated Mar 21, 2025 6:00 AM ET

The name on the stadium hasn’t changed. But clearly, the mindset at the top of the New York Yankees has.

Author of Derek Jeter's biography and veteran New York City columnist Ian O’Connor pointed out what Yankees fans have been screaming for a while: Hal Steinbrenner isn't his father.

And he's not trying to be.

Talking on the Colin Cowherd podcast, O’Connor shared a moment that said a lot — maybe too much — about how the franchise is being run today. When asked why the Yankees weren't spending more to bolster the roster, Hal's answer wasn't exactly the kind of fire-and-fury response fans remember from The Boss.

"There are banks and partners and lenders that I have to deal with, and I have to answer to,” O’Connor recalled Hal saying.

O’Connor, who spent years interviewing George Steinbrenner as a columnist in Westchester and New York City, didn’t mince words when comparing Hal to his dad.

"I never heard him talk about a bank, lender, a bondholder, or a partner ever," he said. "He did not care. I don't even know if he cared about turning a profit — he just wanted to win and win at all costs."

That's the line that'll stick with fans.

Say what you want about George Steinbrenner, but no one ever questioned where his priorities were.

Now, a decade since they last won a World Series, with Hal reportedly mandating the Yankees stay under the $301 million luxury tax threshold this season, it's hard not to wonder what his father would think. Or do.

In the early 2000s, George would've seen a hole in the rotation like the one left by Gerrit Cole's injury this spring and had a new pitcher in camp by lunchtime.

Hal? He's going to wait and see how this works out.

The Yankees still spend plenty. They were the third-highest payroll in baseball last season. But you can imagine The Boss bristling about being third in anything. O'Connor's comments were not really about the dollars. The difference between father and son is urgency and obsession with winning.

In this case, Hal could not be less like his father. At least that's how O'Connor, who wrote The Captain about Jeter in 2011, see it.

This article first appeared on Athlon Sports and was syndicated with permission.

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