The Brian D. O'Leary Show
The Brian D. O'Leary Show

The Brian D. O'Leary Show

Brian O'Leary

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The Brian D. O'Leary Show is where serious analysis meets uncompromising truth. Host Brian D. O'Leary delivers the unvarnished truth and unrelenting insight that other commentators won't touch—covering politics, economics, sports, culture, and faith from a perspective you won't find anywhere else. What You'll Get Hard-hitting interviews with journalists, authors, and thought leaders who aren't afraid to tell the truth In-depth analysis that cuts through media spin and cultural noise Exclusive content unavailable on mainstream platforms This isn't another generic podcast. It's essential listening for serious readers who demand substance over soundbites. Each episode connects directly to The O'Leary Review's mission: delivering the analysis other pundits won't give you. Ready for insights reserved for serious listeners only? Subscribe now and join thousands of readers who've discovered why Brian O'Leary's perspective is reshaping how thoughtful Americans understand our culture. Visit BrianDOLeary.Substack.com for exclusive written analysis and premium subscriber benefits. @BrianDOLeary on the Fountain App, 𝕏–Twitter, Substack, and YouTube.

Recent Episodes

Behind the Curtain of the L.A. Lakers: The Buss Legacy & LeBron's Final Act with author Yaron Weitzman
NOV 13, 2025
Behind the Curtain of the L.A. Lakers: The Buss Legacy & LeBron's Final Act with author Yaron Weitzman
<p>In the latest episode of The Brian D. O’Leary show, we sat down with Yaron Weitzman in a wide-ranging interview that dove into the modern Lakers dynasty, the lasting imprint of the Buss family, and the evolving career of LeBron James.</p> <p> </p> <p>***</p> <p><strong>Featured Guest</strong></p> <p><strong>Yaron Weitzman</strong>: Author, NBA journalist, and insider on all things basketball, discussing his new Lakers book and the deeper drama surrounding LeBron, the Buss family, and team culture.</p> <p>Find Yaron on social media:</p> <p>· X/Twitter (@YaronWeitzman)</p> <p>· Instagram (@yaronweitzman)</p> <p>· TikTok (@yaronweitzman)</p> <p> </p> <p>***</p> <p><strong>Books Mentioned</strong></p> <p><a href="https://amzn.to/4hT7Vvs"><strong><em>A Hollywood Ending: The Dreams and Drama of the LeBron Lakers</em></strong></a> <strong>(Doubleday, October 21, 2025)</strong> | Yaron Weitzman | A behind-the-scenes account of the recent Lakers’ journey, focusing on the politics, personalities, and tensions that have shaped the LeBron-era Lakers.</p> <p><a href="https://amzn.to/3Luzi3b"><em>Tanking to the Top: The Philadelphia 76ers and the Most Audacious Process in the History of Professional Sports</em></a> | Yaron Weitzman | A deep dive into the inner workings of "The Process," chronicling how the 76ers undertook an unapologetic rebuild to become a contender.</p> <p><a href="https://amzn.to/4i0X6aW"><em>Giannis: The Improbable Rise of an NBA MVP</em></a> | Mirin Fader | A New York Times Bestseller tracing Giannis Antetokounmpo’s journey from poverty in Greece to world stardom—a nuanced look at his off-court and on-court evolution.</p> <p><a href="https://amzn.to/440pxQp"><em>Blood in the Garden: The Flagrant History of the 1990s New York Knicks</em></a> | Chris Herring | The definitive story of Pat Riley’s Knicks—physical, controversial, beloved, and often chaotic throughout the NBA’s golden era.</p> <p><a href="https://amzn.to/3LZ36os"><em>Three-Ring Circus: Kobe, Shaq, Phil, and the Crazy Years of the Lakers Dynasty</em></a> | Jeff Pearlman | The inside story of the Lakers’ 1996–2004 dynasty, documenting the unforgettable drama and cultural change led by Shaquille O’Neal, Kobe Bryant, and Phil Jackson. <em>I do not recommend any of Pearlman’s work, as I believe him to be a disingenuous, sanctimonious jerk … Oh, and a liar. But I’m dutifully giving you the resources. –BO’L</em></p> <p> </p> <p>***</p> <p><strong>Key News Stories Discussed</strong></p> <p><em>The Luka Doncic Trade to the Lakers</em> (February 2025):</p> <p>Lakers landed Luka Doncic, Maxi Kleber, and Markieff Morris in a three-team blockbuster trade, sending Anthony Davis to the Mavericks—a move that shifted the balance of power in the West. For full details and quotes from both the Lakers and Mavericks front offices: </p> <p>See ESPN: “Luka Doncic to Lakers, Anthony Davis to Mavs in 3-team trade” (February 2025). <a href="https://www.espn.com/nba/story/_/id/43659380/sources-mavericks-trading-doncic-lakers-anthony-davis">https://www.espn.com/nba/story/_/id/43659380/sources-mavericks-trading-doncic-lakers-anthony-davis</a></p> <p> </p> <p><em>Dallas Mavericks Fire GM Nico Harrison</em> (November 2025):</p> <p>Following the controversial Luka trade and mounting pressure from fans, the Mavericks fired GM Nico Harrison at a dramatic team meeting. For the backstory, front-office statements, and Harrison’s reasoning at the time of the trade: </p> <p> See ESPN: “Mavericks fire GM Nico Harrison amid continued fan angst” (November 2025). <a href="https://www.espn.com/nba/story/_/id/46928742/sources-mavericks-expected-fire-general-manager-nico-harrison">https://www.espn.com/nba/story/_/id/46928742/sources-mavericks-expected-fire-general-manager-nico-harrison</a></p> <p> </p> <p>***</p> <p> <strong>Chael Sonnen on LeBron – The "Same Guy" Allegation</strong></p> <p> </p> <p><strong>Viral Video/Podcast Segment</strong>: </p> <p>Former UFC fighter Chael Sonnen claimed on the Flagrant 2 podcast that he and LeBron James “have the same drug guy.” Sonnen alleged LeBron uses EPO and other PEDs, a claim that’s made waves online but is unsupported by any formal evidence or NBA violations to date. </p> <p>For the podcast segment, see:</p> <p><a href="https://x.com/MavsStan41/status/1633276225442521088">https://x.com/MavsStan41/status/1633276225442521088</a><a href="https://x.com/MavsStan41/status/1633276225442521088?s=20">?</a></p> <p>also …</p> <p><a href="https://heavy.com/sports/nba/los-angeles-lakers/shocking-claims-about-lakers-lebron-james-revealed/">https://heavy.com/sports/nba/los-angeles-lakers/shocking-claims-about-lakers-lebron-james-revealed/</a></p> <p> </p> <p>***</p> <p>If you have a Substack or want to get started on that platform, I just put together a 31-page guide about how to do it. Properly. It’s called <a href="https://briandoleary.gumroad.com/l/blueprint/SUBSTACK"><strong><em>Your Substack Success Blueprint</em></strong></a><em>.</em></p> <p>We talk about Magic Johnson in this podcast, so to pay homage to one of the game’s true greats, the first <strong>32</strong> people to buy <a href="https://briandoleary.gumroad.com/l/blueprint/SUBSTACK"><strong><em>Your Substack Success Blueprint</em></strong></a> will get a sweet <strong>$32 discount</strong>.</p> <p>Use code <strong>SUBSTACK</strong> at checkout. Deal expires after the first 32 purchases, or at the end of the calendar year, whichever comes first.</p> <p><a href="https://briandoleary.gumroad.com/l/blueprint/SUBSTACK">https://briandoleary.gumroad.com/l/blueprint/</a></p> <p> </p> <p>***</p> <p> </p> <p>For press, sponsorship, or guest inquiries, contact brian at briandoleary dot com (you know the drill…).</p>
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35 MIN
The Men Who Made the NFL Unstoppable – Interview with author KEN BELSON
OCT 27, 2025
The Men Who Made the NFL Unstoppable – Interview with author KEN BELSON
<p><strong>Ken Belson on How Jerry Jones, Robert Kraft, and Roger Goodell Built the NFL's $10 Billion Empire</strong></p> <p><strong>EPISODE OVERVIEW</strong></p> <p>In this compelling deep-dive conversation, Brian D. O'Leary sits down with <strong>Ken Belson</strong>, <em>New York Times</em> sportswriter and author of the <strong>Amazon #1 Bestseller</strong> <a href="https://amzn.to/4osO7St"><strong><em>Every Day Is Sunday: How Jerry Jones, Robert Kraft, and Roger Goodell Turned the NFL into a Cultural and Economic Juggernaut</em></strong></a> (Grand Central Publishing, October 14, 2025).</p> <p>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.</p> <p><strong>Runtime:</strong> Approximately 46 minutes</p> <p><strong>Release Date:</strong> October 27, 2025</p> <p><strong>Guest:</strong> Ken Belson, <em>New York Times</em> Sports Business Correspondent and author of <a href="https://amzn.to/4osO7St"><strong><em>Every Day Is Sunday: How Jerry Jones, Robert Kraft, and Roger Goodell Turned the NFL into a Cultural and Economic Juggernaut</em></strong></a> (Grand Central Publishing, October 14, 2025)</p> <p><strong>WHAT YOU'LL LEARN</strong></p> <p><strong>The Modern NFL's Foundation (1993-Present)</strong></p> <ul> <li>Why 1993's labor agreement—not a Super Bowl or dynasty—marks the true beginning of the modern NFL</li> <li>How free agency, salary caps, and 50-50 revenue sharing created unprecedented labor peace</li> <li>The pivotal role of Steelers owner Dan Rooney and Broncos owner Pat Bowlen in shaping the league's economics</li> </ul> <p><strong>Jerry Jones: The Relentless Salesman</strong></p> <ul> <li>How Jones "taught the NFL how to sell" despite alienating fellow owners</li> <li>The Rupert Murdoch deal that transformed television economics forever</li> <li>Robert Kraft's assessment: Jerry can "charm a dog off a meat truck"</li> <li>Why Jones doesn't chase money—he chases <em>the chase</em></li> <li>The "Cowboys peanut butter" philosophy: monetizing everything not nailed down</li> </ul> <p><strong>Robert Kraft: The Real Estate Wizard</strong></p> <ul> <li>The brilliant 7-year strategy to acquire the New England Patriots</li> <li>How Kraft bought parking lots, then the stadium, then finally the team—leaving owners with nothing</li> <li>Why Connecticut and Providence offered sweetheart deals, but Kraft stayed in Foxborough</li> <li>Patriot Place: The revolutionary stadium-as-real-estate-development model</li> <li>How Kraft's unshared revenue strategy changed sports franchises forever</li> </ul> <p><strong>Roger Goodell: The Senator's Son</strong></p> <ul> <li>Goodell's childhood ambition letter: "I want to be NFL Commissioner"</li> <li>The political instincts he absorbed from his U.S. Senator father</li> <li>Why some NFL staffers called him "too nakedly ambitious"</li> <li>Goodell's strategy: schmoozing with owners at every opportunity</li> <li>Why can't he find his own replacement (or won't step down)?</li> <li>Prediction: The next commissioner will be a media expert, not a football insider</li> </ul> <p><strong>Bill Belichick & The Jets Resignation</strong></p> <ul> <li>The Leon Hess succession crisis that drove Belichick away from New York</li> <li>Was there tampering between Kraft and Belichick? The evidence examined</li> <li>Why Paul Tagliabue warned teams to "tread carefully" with Belichick</li> <li>The compensatory draft picks the Jets received—and why they got the short end</li> </ul> <p><strong>The Los Angeles Stadium Saga</strong></p> <ul> <li>Inside the 2016 Houston meeting, where Jerry Jones lobbied relentlessly for Stan Kroenke's vision</li> <li>Why the Rams-only bid beat the dual Raiders-Chargers proposal</li> <li>Paul Allen's rare appearance—and how "The Oracle" swung critical votes</li> <li>Jerry Jones, celebrating with a tumbler of scotch: "He's the salesman. He got his catch that day."</li> <li>How the NFL turned two stadium problems into one world-class solution</li> </ul> <p><strong>Gambling's Stranglehold on Sports</strong></p> <ul> <li>Why Jones and Kraft invested in gambling platforms <em>before</em> legalization</li> <li>How the NFL profits from sponsorships and game data sales—not direct gambling revenue</li> <li>The disturbing shift: from communal Sunday football to atomized, real-time phone betting</li> <li>"The book always wins. The sportsbook's going to win. Now you've got people pissed at the NFL."</li> <li>Brian's fear: economic downturns + player financial struggles = integrity crises</li> <li>The Cleveland baseball team scandal, Jontay Porter's lifetime ban, and the NCAA's dangerous new policy</li> <li>Why allowing college athletes to bet on football is "streamlining the pipeline from amateur athletics to federal indictment"</li> </ul> <p><strong>The Future of the NFL</strong></p> <ul> <li>Why 97% of NFL fans never attend a game—and what that means for the league's priorities</li> <li>"Fans in the stadium are essentially props for TV broadcasts"</li> <li>The COVID revelation: Cardboard cutouts worked fine. Do stadiums even matter?</li> <li>Cable TV's death and streaming's fragmentation: How will fans afford to watch?</li> <li>The NFL's challenge: squeezing every penny without breaking fan loyalty</li> </ul> <p><strong>KEY QUOTES</strong></p> <p><strong>On Jerry Jones:</strong></p> <p>"Jerry taught us how to sell." — Carmen Policy, former 49ers President</p> <p><strong>On Robert Kraft:</strong></p> <p>"He could charm a dog off a meat truck." — Robert Kraft on Jerry Jones</p> <p><strong>On Gambling:</strong></p> <p>"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."</p> <p>"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."</p> <p><strong>On Roger Goodell's Future:</strong></p> <p>"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."</p> <p><strong>On Fans:</strong></p> <p>"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."</p> <p><strong>TOPICS/CHAPTERS</strong></p> <ul> <li>Introduction & Book Overview</li> <li>Why 1993? The Labor Deal That Changed Everything</li> <li>Jerry Jones: The Man Who Brought Rupert Murdoch to the NFL</li> <li>Robert Kraft's Brilliant Patriots Acquisition Strategy</li> <li>Patriot Place & The Real Estate Revolution</li> <li>Roger Goodell's Path: From Senator's Son to Commissioner</li> <li>Bill Belichick's "I Resign as HC of the NYJ" Napkin Moment</li> <li>The 2016 Los Angeles Stadium Decision: Jerry Jones vs. Jerry Richardson</li> <li>Gambling's Corrosive Effect on Sports Integrity</li> <li>The Future of NFL Leadership & Media Fragmentation</li> <li>Closing Thoughts</li> </ul> <p><strong>ABOUT THE GUEST</strong></p> <p><strong>Ken Belson</strong> is a sports business correspondent for <em>The New York Times</em>, where he has covered the NFL, sports economics, and major league developments for over a decade. His latest book, <em>Every Day Is Sunday</em>, 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.</p> <p><strong>RESOURCES & LINKS</strong></p> <p><strong>Order the Book:</strong> <a href="https://amzn.to/4osO7St"><strong><em>Every Day Is Sunday</em></strong> on Amazon</a></p> <p><strong>Connect with Brian D. O'Leary:</strong></p> <ul> <li>Substack: <a href="http://OLearyLetter.com">OLearyLetter.com</a></li> <li>Twitter/X: <a href="https://twitter.com/BrianDOLeary">@BrianDOLeary</a></li> <li>YouTube: <a href="https://youtube.com/@BrianDOLeary">@BrianDOLeary</a></li> </ul> <p><strong>Follow Ken Belson:</strong></p> <ul> <li><em>The New York Times</em>: <a href="https://www.nytimes.com/by/ken-belson">Author Page</a></li> </ul> <p><strong>EPISODE TAGS</strong></p> <h1 id="nfljerryjonesrobertkraftrogergoodellkenbelsonsportsgamblingnflhistorydallascowboysnewenglandpatriotsbillbelichicksportsbusinessmediarightsstadiumdealslosangelesramssportsintegrityfantasyfootballnewyorktimesbriandolearythebriandolearyshow">NFL #JerryJones #RobertKraft #RogerGoodell #KenBelson #SportsGambling #NFLHistory #DallasCowboys #NewEnglandPatriots #BillBelichick #SportsBusiness #MediaRights #StadiumDeals #LosAngelesRams #SportsIntegrity #FantasyFootball #NewYorkTimes #BrianDOLeary #TheBrianDOLearyShow</h1> <p><strong>LISTENER NOTE</strong></p> <p>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.</p> <p><strong>SUBSCRIBE & SHARE</strong></p> <p>If you enjoyed this episode, please subscribe on your favorite podcast platform, leave a review, and share with fellow sports fans who want serious content in an unserious culture.</p> <p><strong>The Brian D. O'Leary Show</strong>: <em>Your sanctuary for serious content in an unserious culture.</em></p>
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46 MIN
Baseball in the ROARING TWENTIES - Interview with author Thomas Wolf
SEP 27, 2025
Baseball in the ROARING TWENTIES - Interview with author Thomas Wolf
<p><a href="https://amzn.to/4msYLGF"><strong><em>BASEBALL IN THE ROARING TWENTIES</em>: The Yankees, the Cardinals, and the Captivating 1926 Season</strong></a> by Thomas Wolf (University of Nebraska Press, September 1, 2025)</p> <p><strong>Quick recap</strong></p> <p>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.</p> <p><strong>1926 Baseball Season Highlights</strong></p> <p>Tom Wolf discussed his new book, <a href="https://amzn.to/4msYLGF"><strong><em>BASEBALL IN THE ROARING TWENTIES</em></strong></a><strong><em>,</em></strong> focusing on the 1926 season, which he selected for research related to his previous book, <a href="https://amzn.to/4nDu0Qv"><strong><em>The Called Shot: Babe Ruth, the Chicago Cubs, and the Unforgettable Major League Baseball Season of 1932</em></strong></a> (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.</p> <p>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.</p> <p><strong>Rube Foster's Vision for Integration</strong></p> <p>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.</p> <p><strong>1919 Black Sox Scandal Investigation</strong></p> <p>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.</p> <p><strong>1926 Baseball Rivalry Insights</strong></p> <p>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.</p> <p># # #</p> <p>Ready for insights reserved for serious listeners only? Subscribe now and join thousands of readers who've discovered why Brian O'Leary's perspective is reshaping how thoughtful Americans understand our culture.</p> <p>Visit <a href="http://BrianDOLeary.Substack.com"><strong>BrianDOLeary.Substack.com</strong></a> for exclusive written analysis and premium subscriber benefits.</p> <p><strong>@BrianDOLeary</strong> on the <a href="https://fountain.fm/briandoleary">Fountain App</a>, <a href="https://x.com/BrianDOLeary">𝕏–Twitter</a>, <a href="https://briandoleary.substack.com/">Substack</a>, and <a href="https://www.youtube.com/@briandoleary">YouTube</a>.</p> <p># # #</p> <p><strong><em>Links</em></strong></p> <p><strong>Books by Thomas Wolf:</strong> </p> <p><strong><em>The Called Shot:</em></strong> <em>Babe Ruth, the Chicago Cubs, and the Unforgettable Major League Baseball Season of 1932</em> (Nebraska, 2020) <a href="https://amzn.to/4nDu0Qv">https://amzn.to/4nDu0Qv</a></p> <p><strong><em>BASEBALL IN THE ROARING TWENTIES</em>: The Yankees, the Cardinals, and the Captivating 1926 Season</strong> by Thomas Wolf (University of Nebraska Press, September 1, 2025) <a href="https://amzn.to/4msYLGF">https://amzn.to/4msYLGF</a></p> <p>*** *** *** </p> <p>Disclaimer: <strong>“As an Amazon Associate, I earn from qualifying purchases.”</strong></p>
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32 MIN