James began filling in as a host on KABC-AM (790) talk radio in 2003 and moved to Oklahoma City the following year to host a morning drive-time show.
In early 2005, he returned to his Laurel Canyon home and switched his registration a third time, back to Republican. The move was prompted by his growing concerns about the economy and his feeling that if he delved more deeply into politics, the GOP would benefit from having more openly gay members in its ranks.
"I thought my work in the Republican Party would be more valuable."
Buoyed by his ratings, he was hired to host KABC's overnight talk slot, "Red Eye Radio."
In 2007, conservative station KRLA-AM (870) hired James to host his own late-night show. Although he still practices law, in late 2011, he left the show to concentrate on his mayoral campaign. James believes he will capture a "significant portion" of the lesbian-gay-bisexual-transgender vote, although he notes the largest concentration of gays in the region live in the city of West Hollywood and can't vote in L.A. races.
James' late-night talk shows began centering on civic issues, starting as a fill-in host at KABC in 2003. During long, middle-of-the-night talks he found his passion, dissecting issues such as taxation, group homes in residential areas, a backlog in processing of rape kits and trigger laws for charter schools.
He also found his followers. Fans of his show are reliable voters, and they're tired of government's slowness and excuses for not bringing about needed change, he says. They're also disgusted by a seeming litany of political scandals, including payouts at the Coliseum, waivers on parking fines for VIPs and a perceived pay-to-play culture in City Hall.
Garcetti, Greuel and Perry have chosen mostly to ignore James. But at a debate in October, Greuel suggested it's much easier to sling arrows than to do the hard work of governing.
"You talk a lot, but where is the action over the years?" Greuel said. "Where is the decision to be literally in City Hall … saying, 'Here's exactly what we need to do'?"
At the conservation league fundraiser, the boyish-faced James, wearing an American flag pin on his crisp gray suit, repeatedly introduced himself with a genial, "Hi, I'm Kevin James." At events across the heavily Democratic city, he says, he finds voters who want to support someone not already connected to City Hall.
He noted that the last Republican to hold the post, businessman Richard Riordan, similarly positioned himself as an "outsider" candidate in 1993 and served two terms. "They haven't had someone to vote for since Riordan," James says, a soft Oklahoma accent just perceptible. "I'm their guy."
Political analysts question, however, whether James has a shot at even making the May runoff election. A recent early poll conducted by Loyola Marymount University put him last among the major candidates, with 8.7% of the vote.
At that rate, he might take votes from Greuel or Perry, both of whom are presenting themselves as business-friendly Democrats. Even if he makes it to the May contest, pundits say, his chances of defeating a Democratic opponent in an overwhelmingly Democratic city are questionable.
James insists he is running a real race and has a real chance. He dismissed the Loyola Marymount survey as a "name ID poll" that shows only that he's not as well-known as the other three candidates. The super PAC backing him shows there is confidence in his campaign, he said.
Davis, who created the funding group, said he decided to help James a few weeks back after meeting him. He found James earnest, articulate and full of good ideas on how to get the city back to financial stability, he said.
"The basic plan is to raise equal dollars or better and use that in a way that gets the message out that he is the one outsider," Davis said. "If you're an insider, you can't fix the problem."