The Brian D. O'Leary Show

The Men Who Made the NFL Unstoppable – Interview with author KEN BELSON

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Ken Belson on How Jerry Jones, Robert Kraft, and Roger Goodell Built the NFL's $10 Billion Empire

EPISODE OVERVIEW

In this compelling deep-dive conversation, Brian D. O'Leary sits down with Ken Belson, New York Times sportswriter and author of the Amazon #1 Bestseller Every Day Is Sunday: How Jerry Jones, Robert Kraft, and Roger Goodell Turned the NFL into a Cultural and Economic Juggernaut (Grand Central Publishing, October 14, 2025).

This wide-ranging interview explores the transformation of the NFL from a beloved sporting league into a ten-billion-dollar cultural phenomenon. Belson reveals the untold stories behind the three most influential figures in modern football history, their business strategies, their political maneuvering, and the existential threats now facing America's most powerful sports league.

Runtime: Approximately 46 minutes

Release Date: October 27, 2025

Guest: Ken Belson, New York Times Sports Business Correspondent and author of Every Day Is Sunday: How Jerry Jones, Robert Kraft, and Roger Goodell Turned the NFL into a Cultural and Economic Juggernaut (Grand Central Publishing, October 14, 2025)

WHAT YOU'LL LEARN

The Modern NFL's Foundation (1993-Present)

  • Why 1993's labor agreement—not a Super Bowl or dynasty—marks the true beginning of the modern NFL
  • How free agency, salary caps, and 50-50 revenue sharing created unprecedented labor peace
  • The pivotal role of Steelers owner Dan Rooney and Broncos owner Pat Bowlen in shaping the league's economics

    • Jerry Jones: The Relentless Salesman

    • How Jones "taught the NFL how to sell" despite alienating fellow owners
    • The Rupert Murdoch deal that transformed television economics forever
    • Robert Kraft's assessment: Jerry can "charm a dog off a meat truck"
    • Why Jones doesn't chase money—he chases the chase
    • The "Cowboys peanut butter" philosophy: monetizing everything not nailed down

      • Robert Kraft: The Real Estate Wizard

      • The brilliant 7-year strategy to acquire the New England Patriots
      • How Kraft bought parking lots, then the stadium, then finally the team—leaving owners with nothing
      • Why Connecticut and Providence offered sweetheart deals, but Kraft stayed in Foxborough
      • Patriot Place: The revolutionary stadium-as-real-estate-development model
      • How Kraft's unshared revenue strategy changed sports franchises forever

        • Roger Goodell: The Senator's Son

        • Goodell's childhood ambition letter: "I want to be NFL Commissioner"
        • The political instincts he absorbed from his U.S. Senator father
        • Why some NFL staffers called him "too nakedly ambitious"
        • Goodell's strategy: schmoozing with owners at every opportunity
        • Why can't he find his own replacement (or won't step down)?
        • Prediction: The next commissioner will be a media expert, not a football insider

          • Bill Belichick & The Jets Resignation

          • The Leon Hess succession crisis that drove Belichick away from New York
          • Was there tampering between Kraft and Belichick? The evidence examined
          • Why Paul Tagliabue warned teams to "tread carefully" with Belichick
          • The compensatory draft picks the Jets received—and why they got the short end

            • The Los Angeles Stadium Saga

            • Inside the 2016 Houston meeting, where Jerry Jones lobbied relentlessly for Stan Kroenke's vision
            • Why the Rams-only bid beat the dual Raiders-Chargers proposal
            • Paul Allen's rare appearance—and how "The Oracle" swung critical votes
            • Jerry Jones, celebrating with a tumbler of scotch: "He's the salesman. He got his catch that day."
            • How the NFL turned two stadium problems into one world-class solution

              • Gambling's Stranglehold on Sports

              • Why Jones and Kraft invested in gambling platforms before legalization
              • How the NFL profits from sponsorships and game data sales—not direct gambling revenue
              • The disturbing shift: from communal Sunday football to atomized, real-time phone betting
              • "The book always wins. The sportsbook's going to win. Now you've got people pissed at the NFL."
              • Brian's fear: economic downturns + player financial struggles = integrity crises
              • The Cleveland baseball team scandal, Jontay Porter's lifetime ban, and the NCAA's dangerous new policy
              • Why allowing college athletes to bet on football is "streamlining the pipeline from amateur athletics to federal indictment"

                • The Future of the NFL

                • Why 97% of NFL fans never attend a game—and what that means for the league's priorities
                • "Fans in the stadium are essentially props for TV broadcasts"
                • The COVID revelation: Cardboard cutouts worked fine. Do stadiums even matter?
                • Cable TV's death and streaming's fragmentation: How will fans afford to watch?
                • The NFL's challenge: squeezing every penny without breaking fan loyalty

                  • KEY QUOTES

                  On Jerry Jones:

                  "Jerry taught us how to sell." — Carmen Policy, former 49ers President

                  On Robert Kraft:

                  "He could charm a dog off a meat truck." — Robert Kraft on Jerry Jones

                  On Gambling:

                  "We went from sitting down with your dad with a clicker, maybe a can of beer, your jersey on, and you watched for three hours. You watched a drama, basically. Now you're betting on a tight end you don't care about because he's on your fantasy roster. Well then you add money to it, and it really amplifies the tension."

                  "The book always wins. The sportsbook's going to win—more chances than not. So now you got people pissed at the NFL or pissed at a player or a team."

                  On Roger Goodell's Future:

                  "My suspicion is that it'll be a media person. That's where the league is now. Two-thirds of its revenue comes from media and sponsorships, not from tickets and beer."

                  On Fans:

                  "Roger likes to say that 97% of NFL fans never go to a game. The fans in the stadium now are essentially props for TV broadcasts."

                  TOPICS/CHAPTERS

                  • Introduction & Book Overview
                  • Why 1993? The Labor Deal That Changed Everything
                  • Jerry Jones: The Man Who Brought Rupert Murdoch to the NFL
                  • Robert Kraft's Brilliant Patriots Acquisition Strategy
                  • Patriot Place & The Real Estate Revolution
                  • Roger Goodell's Path: From Senator's Son to Commissioner
                  • Bill Belichick's "I Resign as HC of the NYJ" Napkin Moment
                  • The 2016 Los Angeles Stadium Decision: Jerry Jones vs. Jerry Richardson
                  • Gambling's Corrosive Effect on Sports Integrity
                  • The Future of NFL Leadership & Media Fragmentation
                  • Closing Thoughts

                    • ABOUT THE GUEST

                    Ken Belson is a sports business correspondent for The New York Times, where he has covered the NFL, sports economics, and major league developments for over a decade. His latest book, Every Day Is Sunday, is an Amazon #1 bestseller and chronicles the transformation of the NFL into the most powerful sports league in American history. Belson's reporting combines insider access, rigorous research, and a business-focused lens that reveals the economic machinery behind America's most-watched sport.

                    RESOURCES & LINKS

                    Order the Book: Every Day Is Sunday on Amazon

                    Connect with Brian D. O'Leary:

                    • Substack: OLearyLetter.com
                    • Twitter/X: @BrianDOLeary
                    • YouTube: @BrianDOLeary

                      • Follow Ken Belson:

                      • The New York Times: Author Page

                        • EPISODE TAGS

                        NFL #JerryJones #RobertKraft #RogerGoodell #KenBelson #SportsGambling #NFLHistory #DallasCowboys #NewEnglandPatriots #BillBelichick #SportsBusiness #MediaRights #StadiumDeals #LosAngelesRams #SportsIntegrity #FantasyFootball #NewYorkTimes #BrianDOLeary #TheBrianDOLearyShow

                        LISTENER NOTE

                        This episode contains candid discussion about sports gambling, league corruption, and the business practices that have fundamentally altered how Americans consume professional football. If you care about the intersection of billion-dollar industries, civic life, and the future of American sports culture, this conversation is essential listening.

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