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Addressing the crowds were the Obama campaign's National Finance Director Rufus Gifford, Press Secretary Ben LaBolt, Digital Director Teddy Goff, Project Vote Director Buffy Wicks, and Jamie Citron, director of the LGBT Leadership Council, a project of Obama for America 2012 and the Democratic National Committee. All except Wicks are openly gay staffers. Other staff also attended, including openly gay Zach Portilla at the Sidetrack event; he most recently worked in the White House personnel department.

At the private home, staffers took questions from the attendees, who seemed wary of being pitched for more money when there is still some question about how full-force Obama will be on gay marriage and some more mainstream issues. While people said they were supportive of the president, they appeared to be assessing how that will translate into donations and action. The Obama staffers assured that in this coming election, constituency groups such as LGBT, youth, women and others will be more involved in the campaign.

The larger and more public event at Sidetrack was billed as an "LGBT Campaign Kick-off." There were handouts promoting all that Obama has done on LGBT issues, in addition to a pitch for a large LGBT event for Obama, featuring the president himself, June 23 in New York City. The host will be Neil Patrick Harris, and tickets start at $1,250. Chicago's Laura Ricketts is among the leaders of the LGBT efforts to re-elect Obama, but she had a plane delay in returning to Chicago for the events.