Trouble, the recently deceased canine companion of the late Leona Helmsley, was the richest dog in New York history. The pooch inherited $12 million when Helmsely passed away, though a judge later knocked the award down to $2 million when he rightly determined that that was enough cash for any dog not named Snoop to live on. Still, rest assured Trouble was a jet-setter while alive, travelling between Helmsley's other homes in Connecticut, Arizona, and Florida. Though, rumor has it Trouble felt most at home in Leona's duplex penthouse overlooking Central Park.