Billionaires are supposed to be ruthless.

David Rubenstein has hired former presidents. He's interviewed thousands of people. And he just told me on my podcast he could never bring himself to fire anybody.

Early on at Carlyle, the private equity giant he cofounded, he would have to fire someone. 

The person would come into his office and explain how great they were at their job. And then somehow they'd walk out with a promotion.

His partners stopped letting him do the firing. 

Then David bought the Baltimore Orioles.

In baseball, when the team loses, somebody has to get fired. Last year it was the manager, Brandon Hyde. Two years earlier, Hyde was Manager of the Year.

David's explanation: it's easier to remove the coach than the players. And owners don't tend to remove themselves.

He wrote a book about all this, Inside the Owner's Box. When he bought the team, he went and interviewed other owners to learn how to be one. Learn and write at the same time. I love that.

My first question: will there even be a baseball season next year? The players' contract runs out in December. The owners want a salary cap. The players hate the idea.

"Nobody knows," he said. 

He said that a lot. Nobody knows who becomes a superstar. Nobody knows if AI creates jobs or kills them.

He's right. Most of the time.

Here's what I learned from David.

Money Doesn't Buy Wins

Since David took over, the Orioles have more than doubled player salaries.

The results haven't followed.

The Mets have one of the richest owners in baseball. No championship. The Dodgers spend big and win. Same strategy. Opposite results.

And the draft? In basketball and football, the top picks almost always make it. In baseball, the number one pick sometimes never reaches the majors. Cal Ripken wasn't a first-round pick. Tom Brady went in the sixth round.

Babe Ruth couldn't get a job managing. Earl Weaver never played a single major league game. He's in the Hall of Fame as a manager.

Credentials predict less than we think.

Shut Up and Walk

During the Orioles deal, a banker on the other side started explaining to David what debt is.

Sitting on David's side was Mike Arougheti, who runs the largest private debt business in the world.

A desperate buyer swallows that. David called it childish and hung up.

He was ready to walk away. He wasn't sure he was the right buyer, and he had plenty of other things to do.

Plus, he didn’t want to seem desperate. He always avoided saying things like "I can't wait to get this deal done. My children want me to get this deal done. This is the highest priority of my life." Say that, and you're probably not an effective negotiator. 

That's his rule. If the other side knows you'll put up with anything, you won't get the best deal.

He went back in eventually. A chance to own your hometown team doesn't come twice.

Just don't tell them your kids are begging you to close.

Why We Care

I asked David the big question. Why does a guy in Baltimore care if the Orioles win? It doesn't put bread on his table.

He said Baltimore has been the stepchild to New York, Boston, Philly and Washington for 200 years. When the Orioles win, Baltimore is as good as anybody.

Then he turned it on me. Why do I care about the Mets?

When I was a kid, it felt like I was winning when they won.

That's it. That's the whole business. Millions showed up for the Knicks parade. None of them own a piece of the team.

"Logic isn't everything in life," David said.

That's why he'll never sell. His parents are buried in Baltimore. He'll be buried there too. The team is his way of paying the city back.

As we wrapped up, he complimented my haircut. Then he asked if I'd ever owned a comb.

I'm 58. He told me that makes me a teenager.

He's sending me a comb. I'll let you know when it arrives.

Click here to listen to the whole podcast.