Episode Details

He admits he was so bad at firing people at Carlyle that he sometimes promoted them instead by mistake...

A Note from James:

On this show, I’m usually the one asking the questions.

But near the end of this conversation, David Rubenstein turned it around on me.

He asked why I care whether the Mets win.

And I didn’t really have an answer.

I said, “I guess when I was a kid, it felt like I was winning when they won.”

And David said, basically, yeah. That’s the whole thing.

David owns the Baltimore Orioles now. And he explained that Baltimore has spent roughly 200 years living in the shadow of cities like New York, Boston, Philadelphia, and Washington. If the Orioles win, somebody in Baltimore who will never make a dollar from the team still gets to feel like they won too.

His new book is Inside the Owner’s Box: Conversations on Power and Leadership in Sports.

And there were two things David told me that I can’t shake.

One: he was so bad at firing people at Carlyle that employees would come into his office to get fired and somehow convince him to promote them instead.

So Carlyle took firing away from him.

He didn’t become better at it.

He just stopped doing it.

And two: since he bought the Orioles, they’ve more than doubled what they pay their players.

The team did not become twice as good.

I’ve spent a lot of money in my life trying to fix things that were never money problems.

And, honestly, I’ve spent a lot of my life feeling like a winner because of things I didn’t even own.

So I wanted to ask someone who actually owns the team what ownership teaches you that being a fan never can.

Here’s David Rubenstein.

Episode Description:

David Rubenstein has spent decades buying companies, building The Carlyle Group, negotiating major deals, interviewing world leaders—and now he owns the Baltimore Orioles.

That last job has taught him a few things the others didn’t.

His new book, Inside the Owner’s Box: Conversations on Power and Leadership in Sports, grew out of conversations with owners including Robert Kraft, Ted Leonsis, Tom Ricketts, Jeffrey Lurie, and others. James asks David what he learned from them now that he has crossed from businessman and sports fan into ownership himself.

The first surprise is that sports ownership isn’t primarily about maximizing profit. David says most owners obsess over something much more emotionally dangerous: winning.

And winning is difficult to buy.

Since David’s group took over the Orioles, player payroll has more than doubled without producing a corresponding improvement on the field. That leads James and David into a larger discussion about luck, accountability, talent evaluation, coaching, and how much credit any leader should take when things go well.

David is unusually comfortable admitting what he doesn’t know. He doesn’t pick every player. He doesn’t choose managers by himself. He relies on people who know far more about baseball than he does.

That same philosophy helped him at Carlyle: understand your limitations, then surround yourself with people whose expertise exceeds your own.

The conversation also turns into a masterclass on negotiation.

David tells the story of nearly walking away from the Orioles deal after an exchange with the seller’s investment banker. The important lesson wasn’t the disagreement itself. It was that even when the deal involved his hometown team—a team he genuinely wanted—he had to be willing to leave.

If the other side knows you will pay any price to get something, David says, you have already weakened your negotiating position.

James and David also discuss hiring, firing, job interviews, sports analytics, AI, betting, media rights, franchise valuations, and why elite a