Anna Wintour has always been an Obama supporter (she donated $10K to Democratic White House Victory Fund in 2008) but to say she's ramped up her support for Obama's 2012 reelection campaign would be an understatement. She's one of Obama's top tier bundlers, which means she's raised over $500,000 for the reelection campaign. She put together Runway to Win, a project in which she recruited big name designers (many of whom Michelle Obama has worn) to create items to be sold on the campaign website. Wintour will head to Chicago on June 12 for a "Runway to Win" fundraiser (she hosted one in NYC back in February, too). And, in perhaps her most visible move in support of Obama, last week Wintour was the subject of a campaign video announcing a contest for potential donors to win the chance to dine with her, Sarah Jessica Parker, and the First Couple at a June 14 fundraiser. A few days later, one of those chatty, casual, Obama emails landed in our inboxes with Anna Wintour's name as the sender. "I don't do this sort of thing often -- get involved with politics, that is," the email reads. "But I'm doing everything I can to support President Obama this summer and fall because it's important that we all do. Nights in New York like this one are a happy side benefit." That video was met with immediate backlash.