Terry Watanabe
"He lost $204 million in a single year. The casinos kept him gambling with free alcohol, painkillers, and round-the-clock access. Then they sued him for the debt."
Terry Watanabe was born and raised in Omaha, Nebraska. He inherited Oriental Trading Company — the Omaha-based novelty and party supply giant his father founded — and built it into a business generating hundreds of millions of dollars in annual revenue before selling it in 1999. He was, by any measure, one of the most successful businessmen Nebraska had ever produced.