Sheldon Adelson

Age: 79
Las Vegas Sands
Fortune 500 rank: 244 Sheldon Adelson has a knack for choosing his bets wisely. The IPO of his casino company Las Vegas Sands in 2004 made him a very rich man. Today, Adelson now controls one of the world's largest personal fortunes, and he hasn't been shy about spending it. According to The New York Times, in 2012 Adelson became the biggest single donor in political history, when he gave more than $60 million to a handful of Republican candidates and causes. Mitt Romney may not have won the presidency, but that wasn't because Adelson didn't do his part. Las Vegas Sands operates casinos, hotels, malls, and resorts in Asia and the U.S. It has a particularly spectacular portfolio in Macau, the largest gaming market in the world and the only Chinese territory where it's legal to gamble in a casino. In Macau, it operates the Sands Macao, the Four Seasons Macao, and the grandiose Venetian Macao, which has 460 table games and 2,200 slot machines, plus a 39-floor luxury hotel tower. The company has, however, run into trouble in the region, and it recently acknowledged that it likely violated some provisions set by the Foreign Corrupt Practices Act.