GOP’s Don Quixote tilts at the biggest windmill in San Francisco

A few days ago, John Dennis waded boldly into the bohemian Caffe Trieste, onetime epicenter of the Beat Generation, looking like a corporate executive arriving for a yacht party: Navy blazer over an open-collar dress shirt, Rolex Submariner on his wrist, neatly trimmed gray hair, smooth handsome face and robin’s egg blue eyes.

He placed a flier on a table in front of Steven Harp, a goateed 69-year-old immersed in a book, “The Cosmic Game,” about psychedelic therapy and “non-ordinary states of consciousness.”

“I’m running for Congress,” Dennis said, introducing himself.

Harp warily scanned the flier, which described Dennis as “a pro-peace candidate” who would “end both wars now,” and his opponent, House Speaker Nancy Pelosi, as “a war hawk” who “voted to fund Bush’s wars.”

Harp looked up, doubt wrinkling his brow. “I’ve never heard this from a Republican before,” he said.

“Well, I’m a different breed,” Dennis said.

“I wouldn’t be talking to you otherwise,” Harp said, matter-of-factly. “But you know that you’re in enemy territory here?”

Oh, yes, John Dennis knows that only too well.

Republicans are so rare in San Francisco that they would all fit comfortably into Candlestick Park. Even though Pelosi is vilified in elections across America this campaign season, the district she represents is so solidly left-leaning that in 11 elections she has never won less than 72% of the vote. She hasn’t run a single TV, radio or newspaper ad in her reelection bid. Most of her critics here think her problem is that she’s not liberal enough.

Pelosi’s Republican opponent this time is a real estate investor with two first names, a dreamer on a journey that everyone calls Quixotic. He’s a Ron Paul acolyte with a libertarian bent who supports legalizing marijuana and same-sex marriage, wants to pull U.S. troops out of Afghanistan and Iraq, and thinks the Patriot Act is an assault on individual freedom. He’s also a fiscal conservative who wants to pay down the federal debt and slash government spending.

It must be said that Dennis has no chance of winning; recent tracking polls give Pelosi a 40-point lead. Nevertheless, he has collected $2.1 million from 35,000 campaign donors — more than 90% of them Pelosi haters from elsewhere in the country. He’s spending it on a staff of six, tens of thousands of mailers, and ads for radio as well as English- and Chinese-language newspapers.

This is his first run for public office. He decided to run because he was concerned about the world in which his young daughter was growing up and was frustrated by the out-of-control spending during the George W. Bush years. “Frankly, I was furious with my own party,” he said.

Choosing this particular race was easy. “This is a huge platform — a chance to run against this very polarizing figure who also is speaker of the House,” he said.

He also thought he would “connect with San Francisco voters on social issues in a way that a traditional Republican wouldn’t,” and in the primary he defeated a more traditional and well-funded Republican who had been the party’s choice in 2008 and had argued that Dennis was a liberal in disguise.

Dennis, 47, insists he’s running to win. But he is nothing if not practical. In this congressional district, which includes most of San Francisco, 53% of registered voters are Democrats, 9.5% are Republicans and most of the rest are independents. If he can double or triple the 10% of the vote that the last Republican eked out, he says, he’ll take it as a sign that, one day, his party might have a chance in San Francisco. Probably not, though.

His campaign has drawn more baffled looks than hostility.

The campaign headquarters is bivouacked on the ground floor of a flatiron building in North Beach, next to Larry Flynt’s Hustler Club (“Home of the Hustler Honeys”) and a couple of blocks from the City Lights Bookstore and Caffe Trieste, where Jack Kerouac and Allen Ginsberg once sipped espresso. A few blocks south is the iconic Transamerica Building and more traditional Republican territory — the financial district.

The first hints that Dennis is not your ordinary Republican are on the office windows, which are covered with rainbow-themed campaign placards, including one featuring a marijuana leaf and another with a peace sign. (Dennis hands out T-shirts with the marijuana leaf insignia in cannabis-friendly nooks of the city.)

The pot poster recently caught the eye of two vacationers who paused to take a photograph. “It’s sure not something you see very often on a Republican campaign poster,” said Michael van Kleeck of Portland, Ore.

Another sign on the window urges passersby to volunteer. “Come say hi,” it says. “We won’t bite.”

As he roams the city, Dennis tailors his message to its colorful patchwork of constituencies. In the business district, he talks about out-of-control federal spending. In the Castro, he criticizes Pelosi for reneging on her promise to make gay rights a priority and vows to fight for repeal of the Defense of Marriage Act and Don’t Ask, Don’t Tell. In Haight-Ashbury, he touts his support for Proposition 19 to legalize marijuana. (“Marijuana should be a Republican issue, for goodness sakes,” he said. “It’s about private property rights.”)

Most everywhere, he talks about pulling American troops out of Iraq and Afghanistan, a popular position in this district.

“Some people have said, ‘You’re really letting your liberal side out,’ ” Dennis said. “But the truth is, someone like me is a perfect fit for San Francisco. I don’t think the federal government has any business legislating morality. You should be able to do what you choose, so long as it doesn’t hurt somebody else.”

As he headed out on a walkabout in North Beach last week, he remarked slyly: “This is kind of brave of us, going into the places where all the Beat poets hung out. It’s pretty liberal around here.”

He stopped in on Beatnik haunts and shook hands in Irish pubs, where Giants fans were gathering to watch a National League championship game. An aide was dispatched back to the office to retrieve a Giants cap; she returned with one that had Chinese lettering. “That’ll work,” Dennis said. (“I’m actually a Yankees fan,” he whispered.)

As he handed out cards outlining his positions, he told bar patrons: “Read it and prepare to be shocked.”

A few folks told him that they, too, were unhappy with Pelosi. Keith Drummond, a mystery writer with a tangled gray beard and an Indiana Jones leather hat, said the speaker “has become a machine entity, playing patty-cake with the idiots in the Pentagon and on Wall Street.”

Dennis listened sympathetically. “She’s not as liberal as people think,” he agreed.

When Dennis moved on to other voters, Drummond said that, as much as he disliked Pelosi, he wasn’t sure he could vote for a Republican. “I haven’t voted for a Republican since Richard Nixon and that was clearly a mistake,” he said.

Dennis lives in the tony Pacific Heights neighborhood with his wife and their 4-year-old daughter. But his roots are in Jersey City, N.J., where his father was a longshoreman and his mother, who worked at City Hall, was a Democratic committeewoman. He grew up in a public housing project, though the family left when he was 13 because it had become too dangerous.

He graduated from Fordham University and co-founded a company that designs ergonomic office furniture. He sold his interest a decade ago and now invests in residential and commercial property.

His early political influences were Ayn Rand, author of “The Fountainhead,” and Barry Goldwater. He supported Ron Paul’s 1988 and 2008 presidential campaigns. His relationship with the national Republican Party is cordial, if not particularly warm.

He met Pelosi for the first time a few weeks ago, when he introduced himself at a function in Washington. She declined his offer to debate.

Dennis believes his political views are closer to the hearts of most San Franciscans. He’s been endorsed by Matt Gonzalez, a former president of the local Board of Supervisors and Ralph Nader’s running mate in 2008, and praised by the antiwar activist Cindy Sheehan (who ran as an independent against Pelosi two years ago). A blogger on the Huffington Post website recently made the case that Dennis “should be a liberal’s pick in San Francisco.”

But that label — Republican — is tough to overcome here.

At Caffe Trieste, Steven Harp remained skeptical even as he quizzed the candidate about why he opposes the war.

“You go to war when your country’s under attack,” Dennis said. “We aren’t under attack. This isn’t my war.”

“That’s not a Republican position,” Harp said. “I guess you’re a San Francisco Republican.”

“Exactly,” Dennis said.

scott.kraft@latimes.com