Team: WNBA Chicago Sky
Years of Ownership: 2006-present
Championships Won and Playoff Appearances: Zero championships / Zero playoff appearances

So far, the former Destiny's Child star is not seeing a return on her investment. Six years in and still no playoff appearances. We know they're an expansion team, but how long do you wait to cut your losses and pull the plug on this operation? Also, who told Michelle a WNBA team was a good investment? We hope the word, minor shareholder, is an overstatement for how much money she's put into this team.