Dinners With Anna Wintour for Obama, Donald Trump for Romney: Rise of Raffle Fundraising

Obama and Romney are using celebrities like George Clooney and Donald Trump as raffle prizes to lure small donors. Ben Jacobs explains the strategy.

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A decade ago, the Internet revolutionized political fundraising. Now, in 2012, it is the raffle that’s being made over. This old-fashioned staple of country fairs and church picnics has now gone Hollywood with both Barack Obama and Mitt Romney raffling off the chance to meet celebrities to lure to small donors to contribute to their campaigns. This resort to glam and glitz, however, may point to a deeper weakness among both campaigns: an inability to get small donors excited.

So far this year, the president’s reelection campaign is facing a major drop-off in the number of donors. Thus, he has amped up the number of raffles and added celebrities to the mix. Rather than just offering a chance to have “dinner with Barack”, the campaign now pitches dinners with Barack and George Clooney and coming soon, Barack, Vogue editor Anna Wintour, and actress Sarah Jessica Parker.

In an era that candidates don’t take matching funds and the only real limitation campaign-finance law imposes on the individual donors is the $2,500 cap on how much a person can give, small donors are at premium.

These raffles are an attempt to pump up the lagging numbers of small donors at low cost. As Democratic consultant Tad Devine points out, “These cost very little money to do…because it’s all online.” They lure in donors who might not ordinarily give money. In fact, the result of one Obama campaign raffle was that former Bush spokesman Ari Fleischer donated $5 to Obama in hopes of winning a dinner. This comes at a very low cost. The campaign essentially just has to pay for the YouTube video to promote the dinner and then food on the lucky winner’s plate.

As little as these raffles cost for campaigns to put on, they cost even less money for people to enter. In fact, they are free. State gambling laws mean that you don’t have to actually donate money to the campaign to enter, something the Obama campaign ran afoul of in 2008, when a contest to greet Obama backstage at the Democratic National Convention in Denver initially required people to make a donation. Further, as The Daily Beast’s Allison Yarrow reported in April, contest winners go through an “intensive screening process before sitting down with the president, with even the dinner discussion topics decided in advance.”

This is not to say there isn’t some level of randomness in the contest. For the contest to win dinner with Obama and Anna Wintour, 50 random entrants are chosen. Afterward, entries are sifted through to “provide for an appropriate range of views, backgrounds, and interests among the winners selected” as well as to guarantee that “awarding any prize to such potential winner [won’t] result in a safety or security risk to any person or persons or . . . the disruption of any event associated with the Promotion.” The Romney campaign imposes similar criteria for their events, which include the opportunity to win dinner with Romney and Donald Trump.

These events aren’t all gravy though. Obama’s most recent web ad featuring Wintour inviting donors to her dinner with the president (followed by a private concert with Mariah Carey) has drawn some opprobrium and mockery from the right. Needless to say, Romney’s event with the self-aggrandizing Trump has drawn its fair share of scorn as well.