The Brian D. O'Leary Show

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)

Jerry Jones: The Relentless Salesman

Robert Kraft: The Real Estate Wizard

Roger Goodell: The Senator's Son

Bill Belichick & The Jets Resignation

The Los Angeles Stadium Saga

Gambling's Stranglehold on Sports

The Future of the NFL

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

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:

Follow Ken Belson:

EPISODE TAGS

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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BASEBALL IN THE ROARING TWENTIES: The Yankees, the Cardinals, and the Captivating 1926 Season by Thomas Wolf (University of Nebraska Press, September 1, 2025)

Quick recap

The discussion between Brian and Tom Wolf centered on Wolf's new book about the 1926 baseball season, which explored notable players like Babe Ruth and the competitive dynamics between teams that year. The conversation delved into the broader sports landscape of the 1920s, including the rise of different sports and the challenges faced by black baseball players during this era. The discussion concluded with an examination of key figures in baseball history, including Rube Foster's role in forming the Negro Leagues and the alleged scandal involving Ty Cobb and Tris Speaker.

1926 Baseball Season Highlights

Tom Wolf discussed his new book, BASEBALL IN THE ROARING TWENTIES, focusing on the 1926 season, which he selected for research related to his previous book, The Called Shot: Babe Ruth, the Chicago Cubs, and the Unforgettable Major League Baseball Season of 1932 (Nebraska, 2020). He highlighted the compelling nature of the 1926 season, which featured notable players like Babe Ruth and Rogers Hornsby, and explored their rivalry despite never playing against each other in the same league. Tom noted that the season's dynamics, including the Yankees' and Cardinals' intense competition, made it particularly interesting.

The discussion focused on the 1926 baseball season, particularly the dramatic career turnaround of Babe Ruth, who went from a poor 1925 season to lead the Yankees to first place in 1926, marking the beginning of his second-half career dominance. The conversation also explored the broader context of 1920s sports, including the rise of college football, boxing, and horse racing, as well as the emergence of the Negro Leagues and the challenges faced by black baseball players during that era. The discussion highlighted how the Black Sox scandal and Judge Kennesaw Mountain Landis's opposition to integration effectively halted the progress toward racial integration in baseball, despite early efforts by managers like John McGraw and Connie Mack to sign black players.

Rube Foster's Vision for Integration

The discussion focused on Rube Foster, a pivotal figure in the formation of the Negro Leagues in 1920, and his vision for integrating baseball. Foster's health crisis in 1926 led to his decline and eventual death. Still, his legacy includes the first colored World Series in 1924 and an 11-game World Series between the Chicago American Giants and the Atlantic City Giants. The conversation explored Foster's ultimate goal of integrating the major leagues, which began to happen with Jackie Robinson in 1948, and his proposal for exhibition games between Negro League teams and Major League teams, which was rejected by MLB owners concerned about the impact of integration on their bottom line.

1919 Black Sox Scandal Investigation

Brian and Tom discussed the alleged scandal involving Ty Cobb and Tris Speaker, which Dutch Leonard claimed was a fixed game in 1919. They explored the history of the scandal, including Cobb and Speaker's retirements under pressure from Commissioner Landis, as well as the $20,000 in hush money paid to Leonard by Ban Johnson. The conversation highlighted the complex relationships and power dynamics between baseball executives and players during this period.

1926 Baseball Rivalry Insights

The discussion turned to the rivalry between the American League and the National League. Tom and Brian explored the careers of several legendary players, the 1927 Yankees' dominance, and Babe Ruth's controversial stolen base attempt in the 1926 World Series. They also discussed the different styles and strategies of the two leagues, emphasizing the historical significance of the World Series when the leagues were more distinct in their approaches.

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Links

Books by Thomas Wolf:

The Called Shot: Babe Ruth, the Chicago Cubs, and the Unforgettable Major League Baseball Season of 1932 (Nebraska, 2020) https://amzn.to/4nDu0Qv

BASEBALL IN THE ROARING TWENTIES: The Yankees, the Cardinals, and the Captivating 1926 Season by Thomas Wolf (University of Nebraska Press, September 1, 2025) https://amzn.to/4msYLGF

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In the latest episode of the Brian D. O'Leary Show, Jim Murphy, the author of the bestselling book INNER EXCELLENCE: Train Your Mind for Extraordinary Performance in the Best Possible Life, discusses the widespread impact and philosophy behind his work. Highlighting how NFL star AJ Brown benefited from Inner Excellence's teachings during critical games, Murphy elaborates on the book's core system that promotes being fully present and mastering self for extraordinary performance. He compares his concepts to those popularized by James Clear in Atomic Habits, emphasizing the importance of redefining success and learning from perceived failures. Murphy draws from his rich background as a former professional baseball player and coach, sharing personal anecdotes and experiences that shaped his understanding of sports psychology and human behavior. He emphasizes the importance of emotional stability, adaptability, and self-mastery both in sports and life. With his heartfelt insights and practical advice, Jim Murphy offers listeners the tools to navigate their lives with clarity, purpose, and resilience.

Find

INNER EXCELLENCE: Train Your Mind for Extraordinary Performance and the Best Possible Life (Grand Central Publishing, April 29, 2025)

at https://briandoleary.com/innerexcellence

After a long delay in production … Brian hosts Scott Fischbuch, a Jungian Typology expert, for an in-depth conversation on personality types and his methods. Scott explains his approach to personality typing, which involves analyzing preferences in conversation, turns of phrase, and behavioral mannerisms.

Brian shares his journey into podcasting and reflects on how his personality type has evolved. Scott identifies Brian's personality type as ISTJ and explains the significance of introverted sensing and extraverted intuition.

They discuss the impact of cultural influences on personality and the importance of effort and team dynamics in professional and personal settings. The episode touches on the nuances of effective communication and the role of empathy and sympathy in understanding others.

Scott's site: ToolsWithScott.com

Brian O'Leary –

Website re-launch: https://briandoleary.com

Los Gatos Review (quarterly magazine): https://losgatosreview.com

The O'Leary Letter: http://OLearyLetter.com

O'Leary's Laws

O'Leary's First Law: Nice is not a virtue.

O'Leary's Second Law: You can't cast yourself out of a tangle.

O'Leary's Third Law: While apologies are often necessary or appropriate, never should you have to explain yourself, particularly for something you believe and are not sorry for.

Column at Substack: https://briandoleary.substack.com/p/theyre-now-calling-it-discourse

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This column on 𝕏-Twitter : https://x.com/BrianDOLeary/status/1814045579301019731

Text of article follows:

They're now calling it 'discourse' What happened to disinformation?

By now, you've probably seen a host of graphics in the swampwaters of social media, hastily cobbled together by run-of-the-mill milquetoast leftists. Virtue-signalers, viz.

A meme gone viral over the last few days is a checklist that attempts to pacify the reader with a bunch of platitudes, one being "Contribute to discourse, not division."

This, of course, is a less-than-subtle dig at non-leftists. Gaslighting. To oppose the leftist agenda naturally causes "division" in the minds of these people.

However, and as a matter of principle, it is really only our people who have been the ones to contribute — and show interest in — discourse so-called. We're the ones with ideas and questions.

They're the ones scolding you and forcing compliance with their inanities.

In other words, the left divides. Their people dismiss you and want you dead.

The underlying motive is still not entirely clear, but it matters not.

Remember if you wanted to learn more about the coronavirus mania and the resulting panic? You were told to shut up, wear a mask, and get injected with vaccines. Any information that did not tow the party line was called "disinformation" and was not allowed within their polite society.

That's division.

Now, it appears that the political left — the most violent and destructive force in the entirety of Western Civilization — still runs cover for those within its ranks. Lately it's for those who express displeasure in the fact that the gunman in Butler, Pennsylvania "missed."

Once again, this is nothing short of division. There is no discourse where this is remotely appropriate. Yet, the talking heads in corporate media circles and the lunatic fringe spouting "conspiracy theories" are nonetheless given free range.

The meme concludes: "We can transcend the bitterness and be better, even when we disagree."

No we can't. They should, however.

It is their problem and it is much more than disagreement. It is an impossibility.

Where there was once a large fissure within the culture, the last several days have revealed a cleaving on that divide.

For it is not tenable to maintain a polity or a culture with people that hate you and want you dead.

These people are your enemies. They are the dividers.

It is personal. They came for your family and your livelihood. They'll do it again.

It is political — which is, to say, little more than the simple distinction between who is a friend and who is an enemy.

And it has nothing to do with elections.

Some people might think there are hard choices to be made. To the contrary — the choices aren't difficult.

Painful perhaps, but pain is part of life. It's unavoidable.

Suffering, on the other hand, is a choice. For too long folks have been entirely too comfortable suffering and enduring under this regime.

Admittedly, the left may be a catalyst for such "victim mentality," but mentality is a choice.

Attitude is also a choice and you are in control of your choices.

As always,

Brian

BrianDOLeary.com

Straight to the email list + our FREE Time Management checklist : BrianDOLeary.com/letter

O'Leary's First Law: Nice is not a virtue.

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The Vintage Mencken (gathered by Alistair Cooke)

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The first and perhaps only presidential debate happened on June 27. Adam Haman and Brian O'Leary have the definitive smackdown of the whole thing.

The fellows awarded a winner and offered some commentary. Hilarity ensues (though not necessarily intentional - it's a factor of who was "debating.")

Adam Haman - https://hamannature.substack.com/

Brian O'Leary - https://briandoleary.com/

O'Leary's FREE e-book Run at Thunder, Vol. 1 - https://runatthunder.com/

Natural Order - https://naturalorderpodcast.com/

Links:

https://briandoleary.com/ep98

https://briandoleary.com/ep97

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