Podcast Summary: The Herd with Colin Cowherd
Episode: The Favorites - Great Moments In Gambling's History Part 4
Release Date: June 20, 2025
Host/Authors: Chad Millman and Matt Mitchell, The Volume Podcast Network
Introduction
In this enthralling fourth installment of Great Moments In Gambling's History, hosts Chad Millman and Matt Mitchell delve deep into the murky waters of 19th-century American gambling. Drawing from Chad's extensive research for his upcoming book, the episode uncovers the rise and fall of notorious gambling figures and explores their lasting impact on today's gambling and professional sports industries.
Elijah Skaggs: The Scaling Syndicate Selling Swindler
Chad Millman opens the episode by introducing Elijah Skaggs, a legendary bookmaker from Lexington, Kentucky, who became entwined with organized crime in the early 20th century.
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Discovery and Connection: Chad recounts his thrilling experience visiting Skaggs' former estate. "[...] I was lucky enough that I called the... stone guy... and he lets me in to see this remarkable piece of sports betting history" (Chad Millman, 05:35).
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Skaggs' Operation: Skaggs started as a horse bettor, quickly ascending to become one of the best in the country. He established a gambling syndicate, training dealers and expanding his influence nationwide. As Matt Mitchell highlights, Skaggs was a "good professor" who built a "remarkable nationwide racket" (Matt Mitchell, 11:40).
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Scaling the Empire: Skaggs wasn’t content with just running local operations. He expanded by funding his brother's operations in California and investing in innovative cheating devices, ensuring his syndicate remained ahead of the law and competitors.
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Downfall: Despite amassing a fortune, Skaggs gambled it away by investing heavily in Confederate war bonds, leading to his financial ruin and death nearly penniless in Texas in 1890. Matt summarizes, "That's the story of Elijah Skaggs, America's crooked pharaoh king" (Matt Mitchell, 19:41).
Notable Quote:
"Elijah Skaggs, the scaling syndicate selling swindler." — Chad Millman (18:35)
The Ties Between Early Gambling and Professional Sports
Chad draws a compelling connection between the illicit gambling operations of the past and the foundation of major American sports teams today.
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Historical Influence: He posits that many early sports franchises were established by gamblers, not industrial magnates. Examples include:
- New York Yankees: Founded by a degenerate gambler known for fixing games and owning one of New York’s largest casinos.
- New York Football Giants: Owned by Tim Mara, a renowned sports bettor.
- Detroit Lions & Cleveland Browns: Established by prominent gamblers associated with organized crime.
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Business Origins: Chad emphasizes, "When people were buying these teams, it wasn't the titans of industry... the only people who were going to do it were sports freaks who were probably betting and had a high tolerance for risk" (Chad Millman, 25:22).
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Modern Implications: This historical backdrop explains the intricate ties between gambling, organized crime, and the evolution of professional sports leagues.
Notable Quote:
"Some of the biggest brands in professional sports were founded by sports betters." — Chad Millman (20:36)
John "Bet a Million" Gates: The Most Notorious Big Money Gambler
Transitioning to another infamous figure, John Gates, Matt Mitchell narrates his meteoric rise and dramatic fall in the gambling world.
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Early Ventures: Gates began as a farmer’s son who detested farm work but found his calling in gambling. His initial success in card games led him to explore the barbed wire business, revolutionizing cattle ranching by making fencing affordable and efficient.
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Business Acumen: By cleverly relocating his barbed wire operations to evade legal issues, Gates amassed a fortune, eventually merging his company with US Steel under JP Morgan's ownership. However, his insatiable gambling habits led to reckless investments and enormous losses.
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Gambling Excesses: Gates was notorious for placing colossal bets, including wagering millions on trivial events like the outcome of raindrops on a window. These extravagant gambles earned him his nickname and ultimately contributed to his downfall.
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Personal Life: Despite his wealth, Gates' personal life suffered as his gambling took precedence over his family, exemplifying the destructive allure of unchecked gambling.
Notable Quotes:
"John Gates, Gambling pioneer scaling syndicate selling swindler war bonds." — Chad Millman (19:41)
"They play a cash poker game for four uninterrupted days and nights." — Matt Mitchell (34:06)
Conclusion: The Enduring Legacy of Gambling's Pioneers
Chad Millman and Matt Mitchell wrap up the episode by reflecting on how historical figures like Elijah Skaggs and John Gates have indelibly shaped the modern gambling and sports landscapes. They highlight the transition from illicit operations to legitimate enterprises, noting that today's major gambling corporations and sports franchises owe much of their foundations to these early, often nefarious pioneers.
Final Thoughts:
"When people were buying these teams... the only people who were going to do it were sports freaks who were probably betting and had a high tolerance for risk." — Chad Millman (25:34)
The hosts underscore the complex interplay between gambling, organized crime, and the professionalization of sports, suggesting that understanding this history is crucial for comprehending today's sports and gambling industries.
Looking Ahead
Chad and Matt tease future episodes, promising more riveting stories from gambling's rich history. They encourage listeners to subscribe, rate, and review the podcast to stay updated with their latest explorations into the fascinating world of gambling.
Reminder:
"Action Network reminds you, please gamble responsibly. If you or someone you care about has a gambling problem, help is available 24/7 at 1-800-GAMBLER." — Chad Millman (39:54)
Note: This summary excludes advertisements, promotional segments, and non-content sections to focus solely on the core discussions and narratives presented in the episode.