He's given countless hours and untold riches to public schools, doing everything from endowing programs to knocking on doors in support of bond measures and often pushing his colleagues to do the same.
"My connection to him has been through the school district, and he's really been a prince," Sup. Tom Ammiano said. "He has even stopped calling me antibusiness. He put a lot of his energy into improving public education, and so he shows it can be done."
Progressives don't always agree with Hellman, but they feel like they can trust him and even sometimes win him over. "If you get a relationship with him and you're always honest about the facts and your own interests, he will listen, and that's pretty remarkable," Mooney said. "He shows a remarkable openness to people who have good ideas."
His appreciation for people of all stripes often causes him to reject the conventional wisdom of his downtown allies, who viciously attacked the Green Party members of the Board of Education a few years ago.
"Everybody said, 'Oh my god, Sarah Lipson, you know, she's a Green Party member, she's the furthest left-wing person on the board,' blah, blah, blah," he said. "And I phoned her up one day and said, 'I'd really like to meet you.' And she's — leave aside the fact that I think she's a very good person as a human being, but she's a very thoughtful, analytic person. Listening to her opinions about things that are happening in the school district, I really respect that. I mean, what do I know about what's going on in the school district? I know more now than I did then. But just getting to know people, and maybe get them to understand my point of view, which isn't that penetrating."
Many of his efforts have received little publicity, as when he saved the Great American Music Hall from closure by investing with Slim's owner Boz Scaggs and helping him buy the troubled musical venue. "There are things that you and I don't even have a clue that he has done," Nayman said.
"He's an interesting guy," Mosher said. "He's one of a dying breed, a liberal Republican. He has a social conscience and wants to use his money to do good."
Actually, calling Hellman liberal might be going too far. In the end, he's still very much a fiscal conservative. He doesn't support rent control, district elections for the Board of Supervisors, taxing businesses to address social problems such as the lack of affordable health care, or limits on condo conversions.
He also opposes the requirement that employers provide health care coverage, which downtown entities are now suing the city to overturn, telling us, "In general, I don't think it's a good idea, because I'm still, even in my aging years, a believer that the marketplace works better than other things.... Universal health care I do believe in, but what I worry is that it's going to be another damned bureaucracy and that it's not going to work."
Yet he doesn't believe wealth is an indicator of worth, saying of his fortune, "It is luck. Most of what you do you aren't better at than everyone."
He doesn't believe in the law of the jungle, in which the poor and weak must be sacrificed in the name of progress. In fact, he feels a strong obligation to the masses.
As he told us, "My mantra for capitalism — and I didn't invent this, but I think it's pretty good — is that capitalism won, and now we need to save the world from capitalism."
Hellman looms large over downtown San Francisco. His Financial District office offers a panoramic view of the Bay Bridge, Treasure Island, the Ferry Building, and the rest of the city's waterfront. He likes to be personally involved with his city and the companies in which Hellman and Friedman invests.