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 athletes don’t necessarily make elite coaches or owners.
But the most interesting lesson comes near the end.
David asks why ordinary people care so intensely about teams in which they have no financial stake.
His answer is that sports allow people to participate emotionally in success. When the hometown team wins, the city wins. And for a few hours, millions of people get to feel that victory personally.
That, David says, is something he never encountered in private equity.
What You’ll Learn:
- Why owning a sports team is fundamentally different from owning a traditional business.
- Why spending more money can improve your odds without guaranteeing success.
- How David separates leadership decisions from luck and outcomes.
- Why knowing your limitations—and hiring people smarter than you—is a competitive advantage.
- What David looks for when interviewing and hiring people.
- Why the ability to walk away is essential in any serious negotiation.
- How analytics, AI, betting, and media rights are changing professional sports.
- Why fans feel genuine personal success when their hometown team wins.
Timestamped Chapters:
[02:00] Firing People and Walking Away From Deals
David previews two themes that recur throughout the conversation: why he was terrible at firing people and why a negotiator must always be prepared to leave.
[02:53] A Note from James
James introduces David, the Orioles, Inside the Owner’s Box, and the strange emotional relationship fans have with teams they don’t own.
[04:13] Will There Be Baseball Next Year?
James opens with the uncertainty surrounding Major League Baseball’s next labor agreement.
[04:58] Why David Bought the Orioles
David explains why sports ownership is less financially motivated than traditional investing and why he sees the Orioles partly as a way to give back to Baltimore.
[06:06] Spending More Doesn’t Guarantee Winning
The Orioles have significantly increased payroll, but David says the results demonstrate why money alone cannot manufacture success.
[06:26] When Do You Fire the Manager?
James asks whether a struggling team’s manager deserves the blame when so many factors determine performance.
[07:34] How Much of Winning Is Luck?
Tom Brady becomes the example for separating brilliant decision-making from the enormous role of uncertainty.
[08:39] When One Decision Changes Everything
James and David discuss whether owners can identify specific decisions that truly altered the trajectory of a franchise.
[10:08] The People Who Make the Baseball Decisions
David explains why he trusts the Orioles’ baseball executives rather than attempting to make decisions outside his expertise.
[10:34] David Rubenstein Was Terrible at Firing People
David admits employees sometimes talked him out of firing them—and even into promotions—so Carlyle eventually gave the job to somebody else.
[11:29] How Do You Evaluate Someone Smarter Than You?
James asks how a leader can judge an expert whose technical knowledge exceeds his own.
[13:19] David’s Rules for a Job Interview
Always have questions. Be prepared. Show curiosity. And don’t make compensation the first thing you ask about.
[15:17] What Sports Owners Have in Common
After interviewing owners across major leagues, David identifies the trait they share most consistently: an obsession with winning.
[16:13] Losing in Public
Unlike many business failures, sports losses happen in front of everyone—and are analyzed every day.
[17:02] Becoming a Public Figure in Baltimore
David describes how owning the Orioles changed the way people recognize and interact with him.
[18:00] Buying a Team Is Personal
James compares Ted Leonsis’s approach to buying teams with David’s much longer negotiation for the Orioles.
[19:04] The Zoom Call That Nearly Killed the Deal
David explains why a condescending explanation of debt irritated him enough to walk away from the negotiation.
[20:19] The Most Important Negotiating Rule
Even when you desperately want the deal, David says you have to establish red lines and genuinely be prepared to leave.
[21:36] Preparation, Advisors, and Hidden Liabilities
David breaks negotiation down to preparation, financial sophistication, good advice, and understanding exactly what you’re buying.
[22:46] Starting Carlyle Was Riskier Than Buying the Orioles
David remembers creating Carlyle with no real business background and far less certainty than he has today.
[23:26] Money Is Not the Solution to Every Problem
Ownership reinforces a lesson David already knew from investing: capital helps, but it cannot compensate for every organizational weakness.
[24:00] Why Baseball Prospects Are So Hard to Predict
David compares baseball’s long development path with the greater predictability of early draft picks in basketball and football.
[25:20] Tom Brady, Johnny Unitas, and Hidden Talent
James and David discuss the stars nobody recognized early enough and the limits of forecasting human potential.
[28:05] Do Great Players Make Great Leaders?
David explains why playing brilliance does not automatically translate into coaching, management, or ownership ability.
[29:17] Know What You Don’t Know
James identifies one of David’s recurring strengths: recognizing his limitations and surrounding himself with people who possess the expertise he lacks.
[31:20] How Do You Actually Turn a Team Around?
David runs through the variables an organization has to examine after a disappointing season, from coaching and player development to health and team chemistry.
[32:00] Surviving Criticism as an Owner
David’s strategy for social media criticism is simple: he doesn’t read it.
[34:16] Why Sports Rights Keep Getting More Valuable
David talks about streaming, global audiences, television economics, and live sports’ unusual ability to keep attracting mass audiences.
[36:20] Finding the Next Great Sport
Investors pitch David everything from pickleball and padel to cricket and women’s hockey—but he admits he can’t reliably predict which will break through.
[36:47] Why Baltimore Matters More Than Baseball
David returns to his real motivation for buying the Orioles: his connection to his hometown.
[38:01] Moneyball Meets AI
James asks how artificial intelligence could push sports analytics beyond the statistical revolution popularized by Moneyball.
[39:35] Statistics Matter—But Athletes Still Have to Perform
David argues that increasingly sophisticated analytics remain secondary to skill, motivation, health, and execution.
[41:10] Lies, Damn Lies, and Sports Statistics
They discuss the limits of metrics like WAR and the danger of mistaking measurement for complete understanding.
[42:00] Prop Betting and the Integrity Problem
David explains why bets on individual player actions can create risks that traditional winner-and-loser betting does not.
[42:55] The One Thing Carlyle Couldn’t Teach Him
Sports ownership reveals an emotional relationship between a business and a community unlike anything David encountered in private equity.
[43:49] Why Fans Feel Like They Won
David turns interviewer and asks James why a Mets victory matters to him personally.
[46:03] Population, Media, and the Future Value of Sports
James and David consider what demographics, immigration, AI, and productivity could mean for the future sports economy.
[47:30] Nobody Knows
The serious conversation ends on uncertainty before David pivots to perhaps the episode’s hardest question: what exactly is happening with James’s hair?
[48:55] Closing Thoughts
James recommends Inside the Owner’s Box and wishes David luck on the rest of his ownership journey.
Additional Resources:
- Inside the Owner’s Box — Simon & Schuster
- David Rubenstein — The Carlyle Group
- Baltimore Orioles Ownership Group
- How David Rubenstein Became Owner of the Orioles — MLB.com
- The David Rubenstein Show: Peer-to-Peer Conversations — Bloomberg
- History with David Rubenstein — PBS
- MLB’s 2026 Collective Bargaining Negotiations
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