SAN FRANCISCO — Nancy Pelosi is, beyond doubt, a figure who will long endure, her name forever pressed into the pages of the nation’s history books.

She is the first — and, so far, only — woman to wield the gavel as speaker of the House. She was indispensable to passage of the Affordable Care Act, better known as Obamacare. Working with presidents of both parties, she twice helped keep the American economy from tanking.

She played political field marshal through numerous election cycles, raising astronomical sums to help push Democrats into the majority. When a doddering Joe Biden threatened the party’s hold on the White House and foreshadowed a 2024 congressional wipeout, Pelosi used her considerable influence to not so gently ease the president aside as Democrats’ nominee for the White House.

Why, then, with so much at stake in November, would one of Pelosi‘s last acts before retirement be mucking about in the elbow-throwing, bone-crunching race between the two San Francisco Democrats vying to succeed her in January?

Is it a grudge she holds against Scott Wiener, the prolific and prolifically ambitious state senator, who boldly launched his candidacy last fall before Pelosi had even announced her plans to retire?

Is it resentment that Wiener’s years-long maneuvering blocked the ascension of Pelosi’s daughter, Christine, who’d been widely talked about as her mom’s name-brand successor? (Instead, she’s running for Wiener’s seat in 2028, or sooner if he makes it to Congress.)

Is it Pelosi once more leaning into her long-standing role as a champion of women and women in politics, which drew her to support Supervisor Connie Chan?

Perhaps it’s a bit of all three.

Pelosi, for her part, told reporters that “nobody knows Congress better than I do” and she believes, simply enough, that Chan “would be the best member of Congress.”

But maybe there’s something more elemental.

“Pelosi is the daughter of a machine politician,” said Eric Jaye, a strategist who’s spent decades working in and around San Francisco politics. “She moves from Baltimore” — where her father was a congressman and mayor — “and becomes initially a lieutenant in the political machine here and, ultimately, the general of it.

“She’s playing by the classic rules of machine politics,” Jaye said, “which is the machine has the prerogative of choosing the line of succession.... Nancy Pelosi wanted to be able to make that choice.”

Peas in a pod

Chan, a leader of the city’s progressive wing and a favorite of organized labor, was languishing until Pelosi delivered her endorsement in the final stretch of the primary campaign. Her imprimatur sent Chan surging past tech millionaire Saikat Chakrabarti to place second behind Wiener.

With less than two weeks until election day, the November runoff appears too close to call, though many give Wiener the edge.

There is little that substantively divides the two candidates, both liberals in good standing. Wiener is considered the more moderate of the two, graded on San Francisco’s very-left curve.

“Connie Chan and Scott Wiener are going to vote the same way 99.9% of the time,” said Jim Ross, another longtime San Francisco political strategist. Further, he noted, it’s going to be years before either acquires the clout needed to be a significant force on Capitol Hill. “That’s just the reality of how Congress works.”

Which makes Pelosi’s heavy involvement in their fratricidal fight all the more striking.

She’s put her hefty fundraising muscle behind Chan, helping narrow Wiener’s financial advantage. She’s appeared in pro-Chan advertising — striding in her trademark stilettos — and lent her Washington communications director to the campaign.

She’s also collared Chan a list of glossy endorsements, including Sen. Adam Schiff, former Sen. Barbara Boxer and San José Rep. Zoe Lofgren, the chair of California’s Democratic congressional delegation. Wiener has Atty. Gen. Rob Bonta and several Democratic House members in his corner.

Gov. Gavin Newsom, a former San Francisco mayor and longtime Pelosi ally, has not endorsed either candidate.

A house divided

San Francisco politics have long been personal, nasty and brutish. The city’s close quarters and intraparty rivalries help make it so, and Pelosi’s intervention has further frayed old ties and strained deep-seated alliances.

Susie Tompkins Buell, a San Francisco philanthropist and one of the Democratic Party’s most influential donors, told Politico she couldn’t understand why Pelosi would use her final months in office to torpedo Wiener’s campaign. She’s spoken to other prominent Democrats, Buell said, who felt pressured to endorse Chan because the speaker emerita hit them up.

“All you do is say, ‘Why, why is this happening?’ ” Buell wondered aloud.

It’s been nearly 40 years — going back to when Pelosi was first elected in 1987— since San Francisco had an open congressional seat. Winning here is tantamount to a lifetime appointment; since 1964, just three people have held the seat Pelosi is vacating.

Both Wiener, who is gay, and Chan, who immigrated to San Francisco from Hong Kong, are bidding to write their own bit of history. Wiener, 56, would be the first out LGBTQ+ person to represent San Francisco in Congress. Chan, 48, would be the first Asian American.

As for Pelosi, her aggressive intervention in the contest won’t even merit “a footnote in her biography,” Jaye said.

Her place in posterity is sealed, regardless of who wins or loses Nov. 3.

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