13. The Ricketts Family, Chicago Cubs
The Ricketts have rehabilitated themselves in the last few years by making smart moves, like hiring Theo Epstein as president of baseball ops and Joe Maddon as manager. But these are all moves they want to get almost anyone but them to pay for: They demanded $150 million in public subsidies in addition to a cut of amusement-tax revenue in perpetuity. They went to war against rooftop owners across from Wrigley for the ability to put up billboards to "fund renovations" that they could easily fund out-of-pocket instead, then floated a minority share ownership scheme because, hey, other suckers!
During the 2012 election, they funded a colossally stupid Jeremiah Wright attack ad complete with a casting call for a "Metrosexual Black Abe Lincoln." The ad was never completed. Maybe they'd have more spending cash if they didn't also fund Dinesh "Thank God I'm Not in Gen-Pop!" D'Souza's shithead book and even more incompetent documentary. Lastly, despite telegenic public tiffs with Hizzoner Rahm Emanuel that pit entrepreneurs against the predation of BIG GUBMINT, the family that made its money off securities and online brokerage is otherwise behind-the-scenes chummy with that union-busting creep who just got dinged for accepting illegal donations from pension managers.