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Warren Hellman, founder of the Strictly Bluegrass Festival, pictured Oct. 5, 2003

Hellman felt strongly about passing along a culture of philanthropy to his children and grandchildren. “Many years ago, we started giving an amount of money each year to our children, and each of them have gotten involved with various charities,” he said. “And now with the grandchildren, we’ve been giving them $200 for every year they’ve been alive, and they have a year to give it away, and if not, it expires. And they’ve really gotten into it. We let them know that there’s no such thing as being too philanthropic.”

Hellman’s politics were a source of intrigue in recent years. In 2008, the lifelong Republican stunned observers when he left the party. Unwilling to leap entirely over to the Democrats, Hellman became officially noncommittal.

“I thought about becoming an independent,” he said. “But I became a DTS — which I first thought was ‘driving while totally stoned,’ but it was in fact ‘decline to state.’ Today, with the whole advent of the tea party and the extreme shift to the right, I think the two parties are further divided than they ever have been in my life.”

Hellman gave generously to Sen. Dianne Feinstein, Rep. Nancy Pelosi, former Mayor Willie Brown and others. Last year, he donated $50,000 to Proposition B — the controversial pension reform measure backed by San Francisco Public Defender Jeff Adachi — before withdrawing his support and aligning himself with labor unions to form a more moderate approach. The measure that resulted from those efforts passed resoundingly last month with Hellman’s support.

But Hellman may ultimately be remembered for his annual valentine to the city: Hardly Strictly.

The festival began as one of Hellman’s quixotic dreams in 2001: to invite some of his favorite artists to play at Golden Gate Park. “Why did I start it?” he reflected in February. “I guess I would say I am like the guy at the cocktail party who swallowed a goldfish — it seemed like the thing to do at the time. I’ve just always loved that kind of music. It was indulging a fantasy — to invite my favorite musicians to come and hang out. And I always wanted to put on a little festival. That first year, I was surprised at how many people showed up. With the recession, I was afraid we’d have to pay people to come.”

In fact, there were two stages and nine acts that first year, and around 13,000 people showed up. “Nobody had any idea what would happen with this thing,” he said.

The festival has grown to a three-day affair, with an attendance of more than 600,000 fans who see world-renowned acts like Emmylou Harris, Steve Earle and Elvis Costello — for free. “I describe the festival frequently as the world's most selfish gift,” Hellman told Forbes. “It's a fantastically selfish gift, but it is a gift. There are hundreds of thousands of people there who are appreciating it. Just being able to do something that is completely not commercial, that is pure, hopefully, pleasure for the participants — to create a surrounding where the musicians and professionals like it as much as the crowd does. How could you have more fun than that? What the hell is money for if it isn't for something like that?”

Hellman also called the festival “the single most fulfilling thing” that he had done.

The festival provided Hellman the opportunity to further his own musical pursuits. His band, The Wronglers, came together at the same time as the festival. Hellman joked earlier this year that he’d gone to a lot of time and expense just to ensure he’d get to play — but despite his self-deprecation, Hellman was an accomplished banjo player and his band was equally talented.

Hellman realized a dream of sorts earlier this year when he recorded an album with one of his idols, the iconic roots renegade, Jimmie Dale Gilmore. The band toured with Gilmore this summer, despite Hellman’s increasing frailty. Hellman was at Hardly Strictly Bluegrass this October as always, smiling and happy to be playing.

He has endowed the festival to continue for at least 15 more years. Hellman related a story of bringing his children together to discuss which of his projects should continue after his death. “When the topic of Hardly Strictly came up, I said, ‘It’s up to you guys.’ One of them said, ‘It’s gone,’ and I said, ‘That was dumb, you just endowed it.’” He laughed heartily.

The festival, he has said, “is as close to heaven as I'm gonna get.”

Hellman cared deeply about some for-profit companies, including the Sugar Bowl ski resort in the Sierras, where his family has been going so long that there is an intermediate ski run — Hellman’s Chute — named for them.

Until recently, Hellman showed no signs of slowing down, and reveled in athletics, a joy to him since his youth. After burning his arm as a child, he took up swimming as physical therapy. By high school, he was an accomplished swimmer and went on to play varsity water polo at Cal.

His wife, Chris, who has suffered from Alzheimer’s disease in recent years, shared his love of the physical activity: she had been a professional ballet dancer and competitive skier in her youth.

Hellman’s love of extreme sports was legend. In one story, his passion for running was such that he decided to run the day after surgical pins were removed from an injured knee. He returned home with blood streaming down his leg.

“I came up with the mantra that pain is your friend. If you can still feel pain it means you’re still moving,” he said in February. “Every Friday I try to run at Crissy Field, and I’d see this elderly guy and always thought, there’s a guy I can beat. But the other day, he just ran right by me. So I’m slowing down, but I’m still moving.”

Hellman participated twice in the Western States Endurance Run, a 100-mile trek through the Sierras. He once fell at the 25-mile marker and broke a rib but finished the event. Hellman completed the Tevis Cup, a 100-mile horse race over the same course, five times. He is also a five-time age group National Champion in ride and tie, a combination of cross-country running and endurance horseback riding.

His love of all things equine and country no doubt influenced his eccentric style of dress, which was once described as “Financial District hobo.” Even at high-level meetings, Hellman eschewed shirt and tie for denim and pearl buttons.

Hellman is survived by his wife, Patricia Christina Sander Hellman, and their four children: Frances Hellman, professor and chairwoman of UC Berkeley’s physics department; Dr. Patricia “Tricia” Hellman Gibbs, a former member of the U.S. Ski Team and one of the founders (along with her husband, Dr. Richard Gibbs) of the San Francisco Free Clinic; Marco “Mick” Warren Hellman, a successful investment banker and champion cyclist; and Dr. Judith Hellman, a physician and associate professor at UCSF; 12 grandchildren; and one great grandchild.

In lieu of flowers, the family requests that donations be made to the San Francisco Free Clinic (sffc.org), The Bay Citizen (baycitizen.org) and the San Francisco School Alliance (sfschoolalliance.org). 

A memorial service will be held Wednesday December 21 at Congregation Emanu-El in San Francisco, and will be followed within a few weeks by a community celebration of Warren’s life.

Jeanne Carstensen, Reyhan Harmanci, Steve Fainaru, Matt Smith, Mia Zuckerkandel and Zoe Corneli contributed to this story.