One night last winter, after he had moved back to DC once again—after he’d worked on Obama’s inaugural address, and the president’s first speech to the joint session of Congress, and many other smaller, more routine policy announcements—Jon Favreau closed up his office in the basement of the White House and met me for dinner. It had been a hard date to schedule. Partly because of his work commitments, but also because he felt he’d already been written about enough. He’d been the subject of a number of newspaper profiles, and had even been chosen runner-up in a "White House’s Hottest" contest sponsored by the Huffington Post. He’d agreed to meet only because my assignment then was to write about him for his college alumni magazine. (When I approached him about this story, Favreau sent me a friendly and polite e-mail, saying, in part, "I think I might pass…I’m trying not to do too many of these." He didn’t respond to any subsequent e-mails or phone messages.)
We met at a new and noisy Latin American restaurant a few blocks from the White House. The president was out of town, taping an interview with Jay Leno in Los Angeles. Favreau ordered a mojito and took out a couple of BlackBerrys, which supplied him with periodic progress reports on Obama’s Tonight Show appearance. "It seems to be going pretty well," he said, after checking one message.
That night, Favreau was a few months from his 28th birthday and seemed to be in the midst of growing up very quickly. He’d achieved the proximity to power that had so entranced him back in college. Almost every day, he spent time in the Oval Office. He was now in charge of a team of six speechwriters, which meant he’d traded in the jeans and sweaters of the campaign for a conservative suit and tie. After two years of living with six people in Chicago, he’d bought a condo near U Street, an area that was fast becoming a sort of subdivision of the subcabinet, home to myriad Obama officials. "DC can get very small very fast," he said.
He learned that lesson the hard way. Not long after he had returned to Washington, Favreau went home to North Reading to visit his parents, who threw a party for him one night. At some point during the evening, a life-size cardboard figure of Hillary Clinton was brought out, and one of Favreau’s friends snapped a picture of him seemingly fondling the effigy of his former opposition. The picture ended up on Facebook, of course, and from there it quickly made the rounds. The New York Post‘s headline: "Barack Writer a Grope-a-Dope." Then the bloggers piled on, questioning everything from Favreau’s maturity to whether the picture portended sexism in the Obama administration.
"I’m sure you’ve seen the Facebook thing," Favreau said to me, after I’d spent a long time not bringing it up. "It was a good lesson. I got very lucky that it was that and nothing else. I wasn’t drunk; I was at my parents’ house. But it could have been in some bar. I’m not a wild partier. But it’s crazy that you have to be so careful.
"And it’s not good enough to say, ‘I’m a good person.’ It doesn’t matter. They’re just looking for anything. And as someone who’s been in this business for a long time and seen [this kind of scrutiny] happen to other people—you really don’t know until it happens to you how enraging it can be.
"You learn it comes with the territory. You learn to be careful."
The rarefied air Favreau travels through now makes him class-A gossip fodder, and the fact that there is little dirt to be found on him doesn’t stop the press from digging to find it. Everything from his salary (a comfy $172,200, on par with chief of staff Rahm Emanuel) to his movement around Washington is newsworthy. Soon after he moved into the West Wing, Gawker reported he was dating someone else in the building, an aide named Ali Campoverdi, a Harvard graduate and former reality-TV star who also happened to be better-looking than anyone who’s ever appeared on Meet the Press. There were even some old pictures of her in sexy lingerie from a shoot for Maxim magazine. In the spring, the gossip sites would buzz with reports that Favreau had hooked up with another Harvard gal, actress Rashida Jones, the daughter of music mogul Quincy Jones and Mod Squad beauty Peggy Lipton. There were reports of the couple together at the White House Correspondents’ Dinner and making out at a bar in Georgetown, and eventually this "sighting" by the New York Post: "Rashida Jones, of NBC’s Parks and Recreation, with current beau Jon Favreau, President Obama’s whiz-kid speechwriter, in the lobby of Favreau’s swanky DC apartment building, the Charleston."
When it came time to choose a date for the gala celebration of Time‘s "100 Most Influential People" issue, where he was listed along with Rush Limbaugh and Oprah Winfrey (prompting a friend to inform him, Favs, you have totally jumped the shark), Favreau picked someone gossip-proof: his mother. Lillian Favreau says her son is trying hard to keep his private life out of the public eye. It’s true she never thought his political career would lead to his dating movie stars. "But after all," she says, in true mom mode, "he is very handsome."