After Nancy Pelosi: A San Francisco Race ‘That Shall Not be Named’

SAN FRANCISCO — Nancy Pelosi has made two very different, almost irreconcilable statements about her political future.

In 2018, she pledged that 2022 would be her last year as House Democratic leader, acceding to a term limit to quell an uprising and secure a second stint as speaker. In January, she announced she was running for another two-year term in the House.

With the House’s passage of the sweeping measure to address climate change and prescription drug prices on Friday — “a glorious day for us,” Ms. Pelosi beamed — and her China-defying trip to Taiwan serving as a diplomatic career capstone, the question of what comes next for Ms. Pelosi is only intensifying.

Will she press to stay on as speaker if Democrats somehow hold the House? Or, if Republicans take control, will she simply retire?

She could break her 2018 pledge and seek to remain Democratic leader in the minority. Those close to her describe only one option as inconceivable: a demotion to the backbench.

Ms. Pelosi, 82, has avoided discussing her plans past November and declined to be interviewed. A spokesman, Drew Hammill, issued the same, terse statement he has offered previously: “The speaker is not on a shift,” he said. “She’s on a mission.”

Some clues to Ms. Pelosi’s future may be found closer to her home in San Francisco — where the tantalizing possibility of the city’s first open congressional seat since the fall of the Soviet Union has become the political talk of the town.

Would-be candidates, labor leaders, political strategists, donors and activists are already busily plotting what a race to succeed her would look like — albeit almost entirely in secret, to avoid antagonizing Ms. Pelosi, who has made plain she wants to retire on her own terms.

“This is very much the campaign that shall not be named,” Dan Newman, a San Francisco-based Democratic operative, said of the early jostling. “Nancy Pelosi is a force of nature, and no one wants to appear in any way disrespectful or dismissive.”

In interviews, more than a dozen officials said local Democrats were preparing for the possibility that Ms. Pelosi could resign rather than stay and hand the gavel to a Republican. That would trigger a snap special election in San Francisco, held within 150 days — a sprint for what, given the city’s politics, could amount to a de facto lifetime appointment to Congress.

Adding to the intrigue: One potential successor is Ms. Pelosi’s daughter Christine Pelosi, a party activist and Democratic National Committee executive committee member who serves as an adviser to her mother, has written a book about her and often accompanies her to local union halls, speeches and parades. She slings her opinions online from a Twitter handle, @sfpelosi, that could at a glance be confused for one her mother might use.

Wrapped up in the elder Ms. Pelosi’s decision and its timing are intertwined questions of power, legacy and dynasty, and how fully a barrier-breaking, notoriously competitive public figure can stage-manage her exit.

There is also Washington politics: Ms. Pelosi called herself “a bridge to the next generation of leaders” four years ago, signaling her desire that her departure coincide with those of her fellow-octogenarian lieutenants, Representatives Steny Hoyer, 83, and James Clyburn, 82. Neither has agreed.

In San Francisco, similarly, the Pelosi name remains beloved, but there is no guarantee of a controlled succession.

A popular state senator, Scott Wiener, whose district overlaps Ms. Pelosi’s, is widely seen as laying the groundwork for a campaign. Mr. Wiener spent nearly $2.5 million on his re-election and has been wooing supporters under the guise of good politics, though his ambitions to become San Francisco’s first openly gay congressman are an open secret.

In an interview at a Brazilian pastry shop, the 6-foot-7-inch Mr. Wiener refused even to broach the possibility of a post-Pelosi era. “The longer she stays, the better for our country,” he said. “I’m on Team Nancy.”

It was a comment befitting what Tony Winnicker, a longtime local Democratic strategist, called “the first rule of wanting to run for Nancy Pelosi’s seat.”

“You never talk about it in a way that suggests Nancy will ever leave,” he said.

Christine Pelosi, too, declined to comment.

As former chair of the women’s caucus of the state Democratic Party, the younger Ms. Pelosi, 56, has been outspoken in fighting sexual harassment.

Increasingly, she and Mr. Wiener, 52, are crisscrossing at local events, like a Pride breakfast where he and the elder Ms. Pelosi both delivered speeches. “This has been a family affair for us for more than 30 years,” Nancy Pelosi said, recognizing her daughter’s presence. (She also acknowledged Mr. Wiener.)

Just as she has in Washington, where she has outlasted a generation of potential male successors — Rahm Emanuel, Chris Van Hollen and Joseph Crowley among them — Ms. Pelosi has kept an array of ambitious local officials on ice since 1987.

Willie Brown, the former San Francisco mayor, said that those planning House campaigns were smart to get started, even if somewhat premature. In an interview over lunch, he speculated that Ms. Pelosi would prove a powerful ally to her daughter, eventually.

“If her mother is not around, Christine would be a formidable candidate,” Mr. Brown said. “Because her mother would make her a formidable candidate.”

Few expect the speaker to reveal her intentions until November. Doing so any sooner could reduce her sway over the razor-thin House Democratic majority, not to mention her power as a fund-raiser. She hosts a major fund-raiser in Napa next weekend, including a cocktail reception at her home.

Whenever her House seat opens up, it will be a chance to not just succeed the first female speaker in United States history but to also represent a city that has long punched above its weight in national politics, despite a population smaller than that of Columbus, Ohio.

Today, the No. 2 and No. 3 officials in the presidential line of succession — Vice President Kamala Harris, once the city’s district attorney, and Ms. Pelosi — both cut their teeth politically in San Francisco. Democrats who emerge in the city’s notoriously cutthroat liberal politics, from Gov. Gavin Newsom to Senator Dianne Feinstein to Ms. Pelosi, have found ways to placate the oft-warring factions of the Democratic Party.

“The fight gives you muscle,” said Debra Walker, an artist and activist who has served as the president of the Harvey Milk L.G.B.T.Q. Democratic Club. Ms. Walker was appointed in June to the San Francisco Police Commission, as Mayor London Breed sought to defuse a blowup between the police department and the city’s annual Pride Parade organizers, who had sought to bar officers from marching in uniform.

Even among Ms. Pelosi’s friends and allies, some have wondered if Christine Pelosi, who wrote a book on campaigning but has never run for office herself, is sufficiently prepared.

“I would rather see Christine start at a state level rather than Congress,” said Joe Cotchett, a major Democratic donor and family friend.

Mr. Cotchett expected Nancy Pelosi to support her daughter, up to a point. “Do I think that Nancy will push her? Emotionally, she’s her daughter,” he said. “But I don’t think Nancy is the type of person who would step in and attempt to block anyone from running.”

If the elder Ms. Pelosi is known for her deft relationship management, that has been less true for Christine, whose years as an activist have included pressing for D.N.C. resolutions — trying to ban corporate contributions, demanding a 2020 climate debate — sometimes to the exasperation of party officials.

Her last name has insulated her from public criticism, but hidden frustrations have mounted, according to a half dozen officials on both coasts.

She antagonized the Newsom team, for instance, when she suggested during the 2021 recall that Mr. Newsom should step down if he looked likely to lose. Publicly, she sought to undercut Mr. Newsom’s central strategy of labeling the recall as a Republican power grab. Privately, she was directly texting Mr. Newsom to complain about his tactics, according to two people briefed on the messages she sent.

Mr. Newsom defeated the recall in a landslide.

In a city where politics is often personal and fractious, Mr. Wiener has accumulated critics, too.

“People talk about it all the time,” Mike Casey, president of the San Francisco Labor Council, said of the race to succeed Ms. Pelosi. “But mostly, like, who don’t we want. Like Scott Wiener has really gotten on the trades’ and a number of our bad side.”

And while Mr. Wiener and Ms. Pelosi are progressives by any national metric, neither would necessarily satisfy the city’s ideological purists, a wing that could field a candidate, too. “I haven’t ruled it out,” said Jane Kim, a 45-year-old former supervisor and executive director of the California Working Families Party.

Jen Snyder, a San Francisco-based strategist who works with progressives, could summon little enthusiasm for a Pelosi-Wiener contest.

“It will be Mothra versus Godzilla,” Ms. Snyder said. “I guess I will be on the sidelines eating popcorn.”

Another possible candidate is Ms. Breed, the first Black woman to serve as mayor. She has indicated she is uninterested in a congressional run, according to people close to her.

“I can tell you as a friend of hers, she’s not,” said Lee Housekeeper, a local public-relations veteran, who joined Mr. Brown for the lunch interview.

“I can tell you as a friend of hers, she better be,” Mr. Brown interjected.

Clint Reilly, who managed Ms. Pelosi’s 1987 congressional campaign and has known her family since, declined at first to talk. “Leave me alone!” he insisted. “They won’t be happy with anything I say!”

But Mr. Reilly, an investor who now owns The San Francisco Examiner, agreed to talk, including about how Ms. Pelosi won that first race, defeating a gay rival, Harry Britt, who ran to her left, in a multicandidate scrum.

Her prophetic slogan: “A voice that will be heard.”

If Democrats lose in November, Mr. Reilly said, “most people would call it at that time.” But not necessarily Ms. Pelosi. “She loves the game,” he said, “She hates to lose.”

“How it ends?” he mused. “I don’t think even she knows the answer.”