Sharp or Square - Covering The World's Best Gamblers with Writer Kit Chellel

In this episode of Sharper Square, hosts Chad Millman and Simon Hunter welcome award-winning Bloomberg reporter Kit Chellel to discuss his new book, 'Lucky Devils: The True Story of Three Rebel Gamblers Who Beat the Odds and Changed the Game.' The conversation dives deep into the secretive world of elite sports betting, focusing on the rise of computer-assisted wagering and the lives of some of the most successful gamblers in history. Chellel reveals how figures like Bill Benter, a math genius who made billions betting on horse racing in Hong Kong using early algorithms, helped lay the foundation for modern sports betting. The episode explores the culture of secrecy among top gamblers, the psychological traits required to succeed—cold-bloodedness, pattern recognition, and emotional detachment—and how technology, especially AI, is now reshaping the arms race between bettors and bookmakers. The hosts and guest also touch on real-world examples like biased roulette wheels, lottery syndicates, and the impact of unique events like the pandemic on betting markets. The discussion underscores that the most successful gamblers aren't lucky—they're disciplined, data-driven, and operate like hedge fund managers in the world of sports betting.