Chateau Margaux, 1875: $225,000
Wine merchant William Sokolin suffered a huge loss in 1989. As he was showing off his prized bottle of 1875 Chateau Margaux, a wine that was discovered behind a wall in a French cellar, the bottle slipped out of his hands and landed on the ground. While the glass didn’t shatter, there were two holes, which leaked all of its contents onto the floor. He’d insured the bottle, though, so the company paid him $225,000 for his loss.