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Bill Kaplan: The Man behind the MIT Blackjack Team

How can one man hatch a plan to legally take Las Vegas for millions? Just ask Bill Kaplan, the official leader of the winning MIT Blackjack team. This group of university students used card counting and team play to win millions of dollars at Vegas casinos. While Kaplan didn’t create the team, he was the one that taught the players how to use card counting to consistently win at Blackjack. And he was the man who turned the team into a money making enterprise that lasted for over ten years.

Team-play Blackjack Sparks Kaplan’s Interest

Bill Kaplan wasn’t always a savvy card player. Back in the mid-seventies, Kaplan attended Harvard University, where he graduated in 1977 as the school’s outstanding scholar athlete. While in Harvard, Kaplan read a book by Ken Uston about team-play Blackjack. The book sparked his interest, and Kaplan began researching and developing a winning team-Blackjack strategy.

Bill Kaplan Scores Successes

Instead of heading to Harvard Business School as planned, Kaplan decided to defer his entry for a year. During this year, he moved to Vegas and formed his very own Blackjack team, using the money that he earned as Harvard’s outstanding scholar-athlete. Some players find that basic Blackjack strategy and card counting are difficult to implement, but Kaplan’s team enjoyed incredible success. After nine months, the team had already earned a thirty-five fold return on Kaplan’s initial investment.

After several years of playing in Vegas, the team was ready to go international. But Kaplan felt that managing a team in a place with different rules and circumstances would be too difficult. He decided to break away from his Blackjack team.

The MIT Team Takes Advice from Kaplan

At the same time, the MIT Blackjack Team was struggling with their game. The members of the team had the skills, but somehow, never came out ahead when it came time to play in a real casino. By chance, a head member of the MIT team, J.P. Massar, overheard Bill Kaplan discussing his Las Vegas exploits in a Chinese restaurant in Cambridge. Massar seized the opportunity, and started a conversation with Kaplan. They discussed the MIT team, and Massar invited Kaplan to observe them in action and provide helpful feedback.

What Kaplan discovered was that the team was not playing in a cohesive way. Every member was using a different strategy, some were making mistakes, and the entire team spent the majority of a weekend in Atlantic City arguing about technique rather than playing Blackjack. Kaplan agreed to take over and coach the team - on one condition. The team had to be run like a business rather than a recreational club. Kaplan wanted to institute a uniform counting strategy, a trial period for every player, casino supervision, and player sheets for every session.

Recreating the MIT Blackjack Team

Although the team members were not initially taken with Kaplan’s ideas, eventually, they decided to go along with his suggestions. Kaplan started the new team in 1980, with $89,000. Just ten weeks later, the team was enjoying a streak of unparalleled success - they had doubled the initial investment.

That was the start of what turned out to be over ten years of incredible team-play Blackjack. Kaplan and Massar continued to recruit and train new players, and operate as an informal business, winning millions of dollars in the process.

In 1992, Kaplan teamed up with John Chang, a long-time MIT Blackjack player and manager, to form Strategic Investments, a new team that was created as an official partnership. They started the team with one million dollars, and were able to beef up their winning capability until casino management began to catch on. Finally, the partnership had to be dissolved - the team morale was low because players were repeatedly asked to leave the local casinos.

The End of Money Making for Kaplan?

While the end of Strategic Investments was the end of Bill Kaplan’s career as manager of a Blackjack Team, it wasn’t the end of his money making exploits. Kaplan went on to found several successful businesses, included Recovery Strategies, Linden Properties, and FreshAddress. He’s currently the CEO at FreshAddress, a company that creates email solutions for businesses. And it’s safe to assume that Kaplan’s winning streak hasn’t yet come to an end.

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