Throughout his life, Pablo Picasso is estimated to have produced about 13,500 paintings or designs, 100,000 prints or engravings, 34,000 book illustrations, and 300 sculptures or ceramics. Thanks to casino magnate Steve Wynn, however, one oil painting will enjoy a greater level of infamy than all of these works.

The painting is titled The Dream, and Picasso completed it in 1932. In 1997, at an art auction at Christie's in New York City, Steve Wynn purchased the painting for 47 million dollars. His purchase actually turned out to be quite an investment. In less than a decade, Wynn completed a deal to sell the painting for $139 million—tripling its value! This transaction would have set a record for the sale of a piece of art. It would have.

Just after completing the deal, Wynn, who was standing close to the painting, turned and inadvertently clobbered the Picasso with his elbow, placing a six-inch hole in the middle of the masterpiece. While no one is certain what this does to the value of the painting itself, the effect on the sale price was immediate. Even more quickly than it had come, the record-breaking $139 million sale evaporated.