Fenway, John Henry and Valuation Thinking

Air Date: 3–31-2026

Today we examine how money and power have captured American sports from every angle — gambling platforms operating as unregulated casinos, private equity turning franchises into financial assets, leagues suppressing player pay while selling access to politicians, and a sports media apparatus too compromised to report any of it. It's almost all the problems with America on display in one industry.

Be part of the show! Leave a voice message, message us on Signal at the handle bestoftheleft.01, or email Jay@BestOfTheLeft.com

Full Show Notes

Check out our new show, SOLVED! on YouTube!

BestOfTheLeft.com/Support (Members Get Bonus Shows + No Ads!)

Join our Discord community!

TOP TAKES

KP 1: Trump's Record $239M Inauguration & the Sports Owners Who Funded It | Spolitics - Jemele Hill - Air Date 4-30-25

KP 2: We Investigated The Shady Business Behind The UFC - More Perfect Union and Luke Thomas - Air Date 3-6-26

KP 3: World Cup CHAOS As Trump And FIFA Abuse Iran - The Ring of Fire - Air Date 3-21-26

KP 4: ESPN & the Death of Journalism - Drew Gooden - Air Date 3-3-26

KP 5: This WNBA CBA Deal Is Bigger Than Basketball… - The Women's Hoops Show - Air Date 3-24-26

KP 6: Senator Chris Murphy CRACKS DOWN on Prediction Markets | PTFO - PABLO TORRE FINDS OUT - Air Date 3-26-26

(00:46:46) NOTE FROM THE EDITOR

Sports Expose Everything Wrong With America — And Fans Have More Power Than They Think

DEEPER DIVES

(00:58:11) SECTION A: SPORTS ARE POLITICS & CULTURE

(01:58:11) SECTION B: GAMBLING ON EVERYTHING IS BAD IDEA

(02:30:27) SECTION C: THE WOKE NBA, NOT THAT WOKE

(03:08:12) SECTION D: THE BILLIONAIRES ARE ALWAYS THE PROBLEM

SHOW IMAGE CREDITS

Description: Composite image of the silhouette of a business man in a suit holding up an upside-down golden umbrella full of sports balls in a celebratory way as money rains down behind him.

Credit: Internal design. Component images from Pixabay

Produced by Jay! Tomlinson

Visit us at BestOfTheLeft.com

Listen Anywhere! BestOfTheLeft.com/Listen Listen Anywhere!

Follow BotL: Bluesky | Mastodon | Threads

Like at Facebook.com/BestOfTheLeft