Sheldon Adelson, CEO of LVS, has the singular distinction of being the person who lost the most dollars in the history of mankind when his 255 million shares of the stock plummeted from $148.80 in late 2007 to as low as $1.38 at the bottom of the crash. He held onto every share and watched his holdings plummet by a cool $37.6 billion. There isn't another soul that ever lost that much. He was briefly the third wealthiest person on the planet according to Fortune Magazine but fell well below $1B at the market lows. With the stock recovering, however, he is currently back to being worth about $12B.