In the 1990s, a team of Blackjack players comprised of students from the Massachusetts Institut of Technology (M.I.T.) laid siege to casinos of Las Vegas. They won millions of dollars by employing an innovative system of "Team Card Counting". In this documentary, the founders of this enterprise, as well as several of its biggest players, discuss the inner workings of their scheme, including recruiting and training techniques and the double lives these students lived: math geeks during the week and Vegas high rollers on the weekend. In addition Anything to Win presents mini-tutorials of Blackjack rules/strategies and takes look at what the gaming industry is doing to thwart the card counters today.