Photography by John Lee.

Mention to Rafael Mandelman that some of his supporters have favorably compared him to Harvey Milk—who initially won the hearts and minds of the Castro community with a pooper-scooper law—and the charismatic lawyer-cum-politician dismisses the comment with a wave of his hand. “That is so sweet,” he says. “That’s too much. He was a lot funnier and a lot smarter.” Smarter? This coming from a Yale grad who went on to get both a law degree from Boalt and a master’s in public policy from Harvard’s JFK School of Government.

“I’ve wanted to be involved in politics since I was a kid,” says Mandelman. “When I was 12, I made a scrapbook of the 1984 presidential election. I thought presidents were like superheroes or princes—politics were as cool to me as that fantasy life.”

Describing himself as an “SF kind of Democrat,” Mandelman recently announced his candidacy for District 8 Supervisor, building his campaign around the progressive tenets he holds most dear—reformed housing policy, real solutions to chronic homelessness, improved urban transportation and gay rights. “I’m afraid of not living a life that is as meaningful and productive as it could be,” he explains. “Those of us who have the ability to do things should do extraordinary things.”

As two-term president of the Harvey Milk LGBT Democratic Club, Mandelman has worked the front lines for the rights of gay, lesbian and transgendered people, even going so far as to get himself arrested in a protest following the passage of Prop 8 last year. “In this city when things are wrong, people want us to fight,” he says. “I’m willing to do that.”

Stylist: Rachel Lena Esterline. Styling assistance: Sonie Hack. Marc Jacobs gray suit jacket ($1,320) and pants ($640), button-down shirt ($395) and cardigan ($840), all at Marc Jacobs, 415-362-6500. Shoes, model’s own.

Check out the other 2009 Hot 20.