In 2006 Steve Wynn put his money on Picasso and lost big. The wealthy art lover had acquired Picasso's La Reve, which if you look closely is a painting of Picasso’s girlfriend with part of her face as a dick. Art is awesome! Wynn was preparing to sell the piece to a buyer for $139 million when he decided to show it off to some friends one last time. That’s when while gesturing wildly while talking, he elbowed the painting, putting a hole in it. After repairs, this knocked the price down to a mere $90 million. The house always wins.