Stephen Jaffe entered the cafe with a small grin, a riotous print shirt and the blithe confidence of someone who doesn't much care if people think he's crazy.
The 71-year-old employment attorney, a political novice, was one of many
But not just any seat.
He hopes to knock off
Not by portraying her the way a succession of failed Republican challengers have, as the lipsticked embodiment of the ludicrous left.
Rather, Jaffe suggests Pelosi is not liberal enough or, for that matter, even a true liberal, a proposition that would be dismissed as outlandish anywhere other than San Francisco.
Here, the political spectrum pretty much runs along a sliver of bandwidth from left to far left to kerplop!, off the continent's edge into the Pacific Ocean.
Enter Jaffe — quixotically — a small part of a much larger heart-and-soul fight among Democrats, between the aggrieved Sanders faction and what, for lack of a new figurehead, remains the Clinton, or establishment, wing of the party.
His platform is very Bernie, including support for universal government-paid healthcare and banishing contributions to the party from a list of corporate villains, among them the oil, pharmaceutical and financial industries.
He also wants to banish so-called "super-delegates," the Democratic party leaders and other insiders who, in the mythological postmortem, cost Sanders the Democratic nomination. (For the record, Clinton would have won even without their support.)
Pelosi, he said, fails the litmus test on all counts and no longer represents San Francisco's progressive values, even if most people outside the city most certainly see her that way. "Nancy Pelosi," he insisted, "is much more popular among Democrats nationally than she is here in her own district."
That would seem to run counter to the available evidence.
After narrowly winning a 1987 special election — against, it's worth noting, several more liberal contestants — Pelosi has been regularly reelected with support in the neighborhood of 80%. Her landslide victories have become so routine, in fact, it has been years since Pelosi ran anything resembling an actual reelection campaign, even as antagonists around the country have poured millions into repeated efforts to beat her.
Does that sound like someone out of touch and wildly unpopular? "It sounds to me," Jaffe scoffed, "like somebody's got a very powerful machine in San Francisco and a very firm grip on the party here."
A spokesman for Pelosi, who makes a practice of ignoring her election opponents, had no comment.
Like every congressional leader, Pelosi serves dual roles.
She is, for good and ill, the national face of House Democrats: an epic fundraiser — a big part of why she has kept her leadership job through myriad political setbacks — and a regular feature of GOP ads portraying the Democratic candidate, whoever he or she may be, as a disciple of Pelosi and her wacky Left Coast liberalism.
At the same time, she is the representative of California's 12th Congressional District, which takes in all but a southwest smidgen of San Francisco.
In that latter role, she has been instrumental in bringing home billions of dollars for the city and its 850,000 residents: for earthquake safety, cleaning up and repurposing old military facilities, funding AIDS research and treatment, expanding public transit and on, at considerable length.
No matter, Jaffe insisted.
"Why would that change?" he asked. "San Francisco is still going to remain San Francisco, whether it's me or Miss Pelosi representing it. We still have the same needs."
But not, absent Pelosi's leadership role, anywhere near the same clout, something the more pragmatic-minded voter might choose to consider. (At age 77, she's had 30 years to build up seniority.)
As if his challenge wasn't formidable enough, Jaffe's campaign has not, to be charitable, gotten off to a terrific start.
Recently, a Facebook posting surfaced from last October, in which he bemoaned his status as "an old white straight" guy in a city where few sins are worse than stodginess and conventionality. "In San Francisco's Democratic Party circles," Jaffe lamented, "we are perceived as a politically incorrect liability."
Over coffee this week, he first tried explaining away the comment — "I had no idea at the time I was going to run for Congress" — then decried the prevalence of identity politics. He invoked the famous words of the Rev. Martin Luther King Jr.
"I don't want to be judged by the color of my skin, or by my age," Jaffe said. "I want to be judged by what I stand for, what I'm able to do for the people of San Francisco."
The plight of the elderly white male may not have been top of the mind for King when he spoke on the Washington Mall, or for the gay rioters outside New York City's Stonewall Inn, but the country has come a long way since then.
Jaffe harbors no illusions about the long odds he faces. Politically, he's charging up a hill steeper than any of San Francisco's vertiginous slopes. "I don't know if I can quantify it," he said, as traffic rushed by outside along the Embarcadero, "but it's certainly very daunting."
But, he went on, recent circumstances give him hope.
"I do think it's possible that I might pull off a spectacular upset and surprise everybody," Jaffe said, "just as our current president did exactly the same thing."
@markzbarabak on Twitter