Bill Kaplan

Bill Kaplan graduated from Harvard University and then earned an MBA from Harvard Business School. His background in business strategy and analytics proved invaluable when he discovered that blackjack could be approached as an investment opportunity rather than simple gambling. He tested card counting theories in Las Vegas and proved they could generate consistent returns.

In the late 1970s, Kaplan encountered a group of MIT students running a small blackjack operation. Recognizing their potential but poor organization, he offered to manage and fund the team using professional business principles. Under his leadership, the MIT Blackjack Team became the most successful and longest-running professional gambling operation in history.

Kaplan approached blackjack team play as a business. He developed rigorous training programs, standardized playing strategies, and careful bankroll management protocols. Only players who passed extensive testing were allowed to play with team money. The team used sophisticated camouflage techniques to avoid detection.

Kaplan's innovation was applying business organization to advantage play. His corporate structure—with investors, managers, spotters, and big players—allowed the team to exploit opportunities worldwide while managing risk. The model he developed influenced virtually every subsequent blackjack team.

The MIT Blackjack Team, under Kaplan's management, won an estimated $5-10 million from casinos over two decades. Their story inspired the book "Bringing Down the House" and the film "21." Kaplan was inducted into the Blackjack Hall of Fame in 2008 and later became a successful entrepreneur, founding FreshAddress and other companies.