Team: Cleveland Cavaliers
Years of Ownership: 2005-present
Championships Won and Playoff Appearances: Zero championships / Five playoff appearances

Just gotta let it burn, huh? We're gonna take a stab here and say he wasn't foreshadowing the city of Cleveland's reaction to LeBron leaving for Miami. That's right, the pop sensation only perpetuated the stereotype that ballers want to be rappers and vice versa. In 2005, Usher bought a piece of Dan Gilbert's Cavaliers and enhanced the madness that was LeBron James. Although, you gotta respect the R&B magnate. The Cavs were hot, making five playoff runs and coming agonizingly close to a ring. And while the LeBron years are gone, Kyrie Irving is just getting started (until he bolts). Come on Cleveland, you know the drill.