“You miss 100% of the shots you don’t take.” – Wayne Gretzky, ‘The Great One’
A fellow like me rarely gets to interview the chairman of the Council on Foreign Relations (CFR) on his show, let alone get the opportunity in the first place. The statistics say that it is a near-zero probability.
The Brian D. O’Leary Show is a relatively small podcast. It’s growing, though we mostly talk about sports on the show these days.
Nevertheless, it happened.
He came on our show. The guy we had zero chance of booking took time out of his day to join us.
On Friday morning, we were fortunate to interview David M. Rubenstein, author of the new book, “INSIDE THE OWNER’S BOX: Conversations on Power and Leadership in Sports” (Simon & Schuster / September 22, 2026).
The conversation centered on sports, however. Not foreign policy or politics.
Rubenstein is indeed the chairman of the CFR, a prestigious think tank that includes politicians, high-ranking government officials, bankers, lawyers, businessmen, professors, and prominent media figures.
To sports fans today, though, he is probably better known as the owner of the Baltimore Orioles, a club in which he bought a controlling interest in 2024.
A Baltimore native, Rubenstein said buying the Orioles was a philanthropic gesture to lift up his hometown. This is precisely the type of sports-related traditionalism we champion here on our platform.
Local owners. Local interest. Local passion.
Real rivalry. Real competition.
Cities and communities need something to believe in. When I was growing up in Portland, we believed in the Blazers. “Blazer Believer” signs and t-shirts were ubiquitous in the Rose City during the heyday of the Trail Blazers. We believed.
Winning a lot certainly helped, though the Trail Blazers have only won one World Championship.
Portland’s love affair with the Blazers was about the people. Not only the players and coaches, but the ownership. Owner Paul Allen was not from Portland. He was from the Seattle area, but he gave Portland a huge gift and a huge lift by buying and investing in its basketball team.
The city government never appreciated the gift Allen gave the city and the fans.
Perhaps Rubenstein can give Baltimore what Allen gave to Portland. Hopefully the politicos don’t squander the gift like what happened in Portland.
Baltimore and Portland have both fallen on hard times thanks to societal unrest, poor leadership, and virtually zero accountability.
HBO’s series The Wire showed a side of the Charm City that most Baltimoreans would prefer not to see and certainly don’t care to address.
Portland was parodied in the sophomoric Portlandia, starring Saturday Night Live’s Fred Armisen. That series left many longtime Portlanders shaking their collective heads in disgust and bewilderment. “We’re nothing but a punchline,” said many.
To be fair, there may have been a chuckle here and there from those who watched on occasion.
The producers of Portlandia even had a paid subscriber to UNRELENTING and guest on our show, Dwight Jaynes, guest-star in their program.
In Portland, there was also Grimm, an NBC show that yours truly had a bit part in. One scene. One episode. But that show was literally the fairy-tale version of the Rose City.
Again, take the shots on goal. You might not put everyone past the goalie, but as Gretzky said, you miss 100% of the shots you don’t take.
Fight for your city, your state, your country, if you believe in it at all. Fight for your family.
A remnant out there still fights for and has passion for their hometown. At its core, it’s a patriotic instinct.
The problems in today’s cities are bigger than money. Solving them requires effort, vision, and passion.
Portland has a few patriotic citizens. Some have vision, some have passion, and a few are willing to make the effort. Not enough, however.
In Baltimore, David Rubenstein is the man of the hour. He’s trying to turn around the city that he was raised in. His first step was buying a controlling interest in the Orioles in 2024.
When Rubenstein grew up, Baltimore was the 9th biggest city in the nation, approaching 1 million residents. It’s a little more than half that size now.
For generations now, Baltimore’s biggest export has been its people.
In our short interview, Rubenstein and I touched on some important topics.
We talked about the Orioles’ history of largely Baltimore-connected owners, the challenges of building a winning franchise, and the disappointment of a recent playoff elimination despite increased payroll, major stadium upgrades, and an injury-plagued 2026 season.
Rubenstein explained modern sports ownership structures, including the role of a controlling owner, growing private equity participation through minority stakes, and his firm’s (Carlyle Group) sports investments, including a recent investment in the Super Bowl champion Seattle Seahawks.
He also addressed my question about the rise of legalized sports gambling, which led to his take on the integrity risks of prop bets, and the need to educate and police players.
One takeaway
In his book, Rubenstein writes:
I am pleased that I made the investment. I think it did—and will—help with the ongoing rejuvenation of Baltimore. I reconnected with my hometown and friends from my youth. I learned more about a sport that I had relished as a boy. And I felt that I was part of a team of professionals trying hard to bring glory back to Baltimore.
I hope he is correct. And I hope he is successful.
For Baltimore. For sports. For the nation.
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Buy the Book
Click the link to buy at Amazon.
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About the Episode
Chapters
♦ Meet David Rubenstein
♦ Baltimore Roots and Civic Pride
♦ Adley Rutschman Trade and Baseball Fandom
♦ Baltimore Baseball History
♦ Private Equity in Sports
♦ Fans and Community Identity
♦ Sports Gambling and Integrity
♦ Local Owners vs Outsiders
♦ Orioles Season and Next Year
♦ Camden Yards Renovations
♦ Roster Notes and Wrap Up
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About the Guest
DAVID M. RUBENSTEIN is an investor, philanthropist, interviewer, author, and historian. He is Co-Founder and Co-Chairman of the Carlyle Group, one of the world’s largest and most successful private investment firms. Established in 1987, Carlyle now manages around half a trillion dollars from twenty-eight offices around the world.
Mr. Rubenstein has served as chairman of the boards of the John F. Kennedy Center for the Performing Arts, Duke University, and the Smithsonian Institution.
He is a Baltimore native and is the chairman, CEO, and principal owner of the Baltimore Orioles.
You’ll also see him hosting The David Rubenstein Show: Peer-to-Peer Conversations on Bloomberg TV and PBS, Bloomberg Wealth with David Rubenstein on Bloomberg TV, Longevity with David Rubenstein on Bloomberg TV, and “America’s Book Club” on C-SPAN.
Rubenstein is the author of five books published by Simon & Schuster.
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