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2. Nicky Hilton

Leveraging her family’s hospitality pedigree, Hilton decided to set up a hotel chain in 2006. She had plans to develop a 94 room hotel on Miami’s Ocean Drive, and another one in swanky Chicago. The Miami hotel was supposed to open in time for the 2007 Super Bowl, but it never did. Indeed, the same year the developer sued the heiress to the Hilton hotel empire for breach of contract.

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