Bill Kaplan
Childhood
Bill Kaplan graduated from Harvard University in 1977 with a degree in applied mathematics. Though not initially an avid gambler, his interest in blackjack was sparked after reading a book on card counting during his college years. Intrigued by the mathematical edge it provided, he began researching optimal strategies for beating the game.
Instead of pursuing further education immediately, Kaplan took a year off and moved to Las Vegas, using his graduation money to fund his first blackjack team. Within nine months, his team had generated substantial profits, proving that his systematic approach to card counting was highly effective.
Career
After three successful years with his initial team, Kaplan parted ways and later encountered J.P. Massar, a member of the original MIT Blackjack Team, which was struggling financially. Kaplan agreed to assess their strategy and quickly identified flaws in their approach.
Taking charge, Kaplan restructured the team with a business-like model—recruiting skilled players, enforcing strict bankroll management, and standardizing card-counting techniques.
For over a decade, the MIT Blackjack Team dominated casinos worldwide, earning millions. In 1992, Kaplan co-founded a new team with John Chang, investing $1 million. Despite early success, increasing casino countermeasures and internal challenges led to the team’s eventual dissolution.
Personal life
After retiring from professional blackjack, Kaplan shifted his focus to entrepreneurship. He became the CEO of FreshAddress, a successful email solutions company. Though no longer an active card counter, he occasionally enjoys casino games and maintains his winning edge.
Revenue
While exact figures remain undisclosed, Kaplan’s teams reportedly earned millions during their peak years. His disciplined bankroll management and team-based approach maximized profits while minimizing risks.
Interesting facts
Kaplan was not a founding member of the MIT Blackjack Team but became its most successful leader.
He applied Harvard Business School principles to manage the team like a corporation.
Unlike other famous card counters, Kaplan avoided the limelight despite his success.
Legacy
Kaplan’s legacy lies in proving that blackjack could be beaten systematically with teamwork, discipline, and strategic planning. His methods influenced modern advantage play and inspired books like Bringing Down the House and the film *21*.
Frequently asked Questions
Kaplan became interested in blackjack after reading about card counting in college. He later moved to Las Vegas to test his strategies, leading to his successful career.
He restructured the team, implemented strict business protocols, and trained players in advanced card-counting techniques, turning it into a profitable enterprise.
Exact figures are private, but estimates suggest millions in profits over a decade.
Increased casino surveillance, team morale issues, and legal pressures made sustained success difficult.
He runs FreshAddress, a successful email solutions company, and occasionally plays blackjack recreationally.
