In October of 2009, tens of thousands of LGBT people marched on Washington, lambasting President Obama for what they saw to be a totally underwhelming agenda on gay rights.

What a difference a year and a half can make. Since that time, when Andrew Sullivan loudly declared that Obama’s speech at a gay rights event was little more than “bullshit…campaign boilerplate,” the president has signed a major hate crimes prevention act, repealed Don’t Ask, Don’t Tell, refused to support the Defense of Marriage Act, and now the latest: appointed Jeremy Bernard as the first man and the first openly gay person to be the White House social secretary, replacing Julianna Smoot, who’s leaving to go work on the president’s re-election campaign.

“It’s a big week for gay rights,” said Corey Johnson, the political director for Towleroad, the influential gay blog.

Further, Bernard’s ascension is a sign that neither the “shellacking” Obama took in the mid-term elections nor the crucifixion of his ex-social secretary Desiree Rogers back in 2009 are going to keep the president from making bold, occasionally eyebrow-raising choices—which in some way, Bernard is.

Talk to people who know the president’s new pick and the words that come up indicate an extroverted quality that’s somewhat at odds with what’s ordinarily expected from those around Obama. Bernard, who is 49 and most recently served as the chief of staff to the U.S. Ambassador to France, is “gregarious” and “electric,” they say. He carries himself with “flourish” and “panache.” He may not cut as wide a swath as Rogers, but he’s probably closer to her than his immediate predecessor, Smoot.

At the time Bernard got involved with the Obama campaign, it was by no means fashionable in gay circles.

"Jeremy is not a safe choice if safe choices mean having someone like Mamie Eisenhower’s social secretary, somebody in the traditional Republican sense," said Marc Nathanson, the billionaire businessman from California whom Bernard worked for through much of the nineties. "He’s a person with energy, drive, and creativity. He is not going to fade into the background." Even Bernard's clothes are bolder than what you'd expect from a Washington insider, Nathanson said. “I’m a Brooks Brothers man..He’s more Versace.” (“He’s not that slick,” another friend, Hilary Rosen, cautioned moments later. “But he’s been in Paris for the last six months and I’m sure he’s upgraded.”)

Growing up in San Antonio, Texas, Bernard’s father was a lawyer who did extensive civil rights work. Though he matriculated at Hunter College after high school, Bernard never graduated—an interesting tidbit that did not go unmentioned when Obama appointed him to the National Endowment for the Humanities two years ago.

Out of the closet from a fairly young age, he earned his stripes working for David Mixner, who went from being Clinton’s gay consigliere to one of his fiercest critics on Don’t Ask, Don’t Tell. “It was Jeremy who bailed me out of jail when I got arrested protesting at the White House,” Mixner recalled.

In the mid-90s, Bernard headed west, where he went to work for Nathanson. Running a large cable company involved extensive work lobbying government officials, and Bernard became the go-to guy in charge of those efforts, said Nathanson, who described his protégé as “extremely effective and hardworking.”

From there, Bernard moved further into Democratic fundraising, a natural fit for a guy who by all accounts loved going to parties and loved to entertain. “Jeremy is very social,” said Nathanson. “There was never a party he did not like to go to.”

And, as Andy Spahn, the man in charge of philanthropy efforts for Hollywood heavyweights like Steven Spielberg and Jeffrey Katzenberg, put it, Bernard was also the kind of person who recognized the importance of having allies in all sorts of different places. “He made a lot of friends in Los Angeles and it cut across town, from the entertainment community to the business community to the gay community to the political community.”

This positioned him well in the work he did for the Clintons, Al Gore, Howard Dean, and John Kerry. Then, in the last presidential election, he worked prominently as a California fundraiser for Obama, working with his then-boyfriend, Rufus Gifford (now the finance director for the Democratic National Committee).

At the time Bernard got involved with the Obama campaign, said Elizabeth Birch, the former head of the Human Rights Campaign, a gay rights group, it was by no means fashionable in gay circles to be pro-Obama. “He signed on really early, which makes him different than a lot of gay leaders. Jeremy was in there early and was dedicated and loyal and unwavering.”

After the president was elected, Bernard and Gifford moved to D.C, where they landed power jobs—Bernard as the White House liaison at the National Endowment for the Humanities, Gifford as the finance director for the DNC—and slots on VIP lists.

In an article in The Washington Post, Gifford admitted that he and Bernard fretted over whether their new digs were big enough to host in. “We had that conversation,” he said. “Is it big enough to entertain?” (Though they determined that it was, the relationship soon soured).

Bernard had his detractors in D.C., who occasionally grumbled that he lacked a background in the arts to justify his position, or that he got the job as a thank-you for his fundraising efforts. But as Birch saw it, neither of these things is noteworthy. “How do you become an expert in the humanities?” she said. “It’s a pretty broad area, you don’t necessarily get a degree in it…If Jeremy got an appointment in part because he was loyal to Obama, that’s hardly unprecedented.”

Now, as he ascends to this more high-profile position, carrying with him some Rogers-esque glitz, some of the detractors will invariably emerge.

Still, few think he’ll wind up in the same position as his predecessor, hung out to dry when a reality TV wannabe crashes an event.

Before getting off the phone with me, his former boss, Nathanson, recalled a fundraiser he and Bernard did for Bill Clinton, which he said illustrates Bernard’s superior screening skills. “Even though I was the chair of the event, the Clinton people wanted to be in charge of screening all the donors. We were put in the background, which we weren’t used to. So at the event, we were looking at the guests, and Jeremy said, ‘I can’t believe it they let such and such in.’ But the campaign staff had taken their money and let them in. So we went over to the campaign staff, and said ‘Who are those people?’ And they said, ‘It’s a man from San Diego and his nephew.’ And Jeremy snickered and said, ‘No. That’s a gay porn producer and one of his stars.’ So obviously the campaign staff with all their security and preparation did not know as much about the potential donors as Jeremy Bernard did.”

Jacob Bernstein is a senior reporter at The Daily Beast. He has also written for New York magazine, Paper, and The Huffington Post.