Who is Bill Kaplan?
Nowadays, Bill Kaplan is the CEO of Massachusetts-based email marketing intelligence company FreshAddress, but will always be best remembered as the co-leader of the Massachusetts Institute of Technology (MIT) Blackjack Team. Indeed, Kaplan provided the inspiration, at least in part, for the ‘Micky Rosa’ character, played by Kevin Spacey, in the 2008 film ‘21’, which was loosely based on the true story.
Kaplan graduated from Harvard University in 1977, but deferred his entry to Harvard Business School – from which he would eventually graduate in 1980 – to focus on building and running a blackjack team in Las Vegas. That he did, with no little success, including as a secondary activity while enrolled at Harvard, until the team disbanded shortly after his graduation.
Thereafter, a chance meeting with J.P. Massar, who was already a member of a not-altogether-successful blackjack team, of sorts, at MIT led to the formation of a new team, based on sound business principles and practices. Under the auspices of Kaplan, Massar and, later, John Chang, another MIT graduate, the MIT Blackjack Team continued to prosper.
In 1992, they formed Strategic Investments, a limited partnership that raised $1 million to bankroll the team. Strategic Investments was dissolved in late 1993, in the face of increased scrutiny from casinos and more lucrative investment opportunities elsewhere, at which point profits were distributed to players and investors. Nevertheless, in its heyday, the MIT Blackjack Team had up to 80 members and was the scourge of casinos throughout the United States for over a decade.