Representative Nancy Pelosi was the first woman to hold the House speaker's gavel, the architect of the Affordable Care Act and two presidential impeachments, and, for nearly four decades, one of the most feared vote-counters in the history of American politics.
Now, in the final months of her last term, she is trying to do one last thing: choose her own successor. The answer, at least so far, is not guaranteed.
State Senator Scott Wiener is leading the June 2 primary by double digits. Pelosi's endorsed candidate, San Francisco Supervisor Connie Chan, is polling in second or third place, neck and neck with Saikat Chakrabarti, a former chief of staff to Representative Alexandria Ocasio-Cortez and co-founder of the left-wing Justice Democrats.
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Under California's "jungle" primary system, the top two vote-getters advance to the general election, regardless of party. If Chan finishes third, Pelosi's most personal political bet of the post-speakership era will have failed.
A Late Bet on Chan
As Chan struggled to gain traction in the polls, Pelosi delivered her formal endorsement on May 18, just two weeks before Election Day, after weeks of publicly praising the San Francisco supervisor while withholding an official endorsement.
The latest EMC Research poll, which surveyed 542 likely voters from May 3-7, showed Wiener at 38 percent, Chan at 22 percent and Chakrabarti at 21 percent.
In a video, Pelosi described Chan as the "leader best prepared to carry forward the fight for San Francisco in the Congress of the United States."
"Connie understands San Francisco, our values, our diversity, our communities and our responsibility to lead with both compassion and strength," Pelosi said.
David McCuan, a political scientist at Sonoma State University, said the timing reflected concerns about Chan's campaign performance on the ground.
"One reason for Representative Pelosi's endorsement is that Supervisor Connie Chan has underwhelmed in the retail politics of being on the ground and meeting, and growing, any sense of a coalition," McCuan told Newsweek. "She's simply been unimpressive in the small scenes on the ground and with the voters in a smaller setting in order to tip those meetings into big-ticket voter conversions and into voter support. Her punches haven't landed."
McCuan was direct about what the endorsement was designed to do. "Hence, the Rep. Pelosi 'magic' was designed to give the Chan campaign a boost—and to put some space between the other two candidates with an eye on November," he said.
Chan previously told Newsweek the race is about delivering for working people.
"We want to bring a San Francisco voice and San Francisco values to Washington," she said. "San Francisco is a union town, and we're very proud of the working people's agenda. We know this is a time that we got to deliver for the working people."
Money vs. the Machine
Jim Ross, a veteran California political strategist, said the race's central tension has less to do with Pelosi's standing than with the role of money in a post-Citizens United political landscape.
"The issue in this campaign is not ideological or generational but economic," Ross told Newsweek. "Less than two years after a billionaire self-funded his way to becoming mayor, can a centimillionaire self-fund his way into a congressional run-off? If Connie Chan loses, it will reinforce the impact of unlimited money on local races, overcoming even strong support from respected leaders like Speaker Pelosi and labor."
Ross also identified a stylistic divide in the race that runs deeper than policy.
"There is a stylistic difference with Chakrabarti, who takes on a more combative, anti-establishment tone, while Chan, though more progressive than he is, is much more moderate in tone," he said. "There is a part of the Democratic base that wants a person who will fight the status quo, but the policies and issues are secondary to the fight itself. Chakrabarti is getting traction because people see him as a fighter."
Chakrabarti has made Pelosi's era itself part of his argument. "The one thing people don't like more than Donald Trump is a feckless and ineffective leadership in the party," he previously told Newsweek.
Two Establishments, One Race
Matt Bennett, co-founder of Third Way, a centrist think tank, pushed back against any simple reading of the field as Pelosi's machine versus the insurgents.
"There are really two establishment candidates in that race: Chan and Scott Wiener," Bennett told Newsweek. "Chan has Pelosi, and Wiener has a bunch of the other federal, state and local elected officials, the local papers, and so on. The only rejection of the old guard would be a Chakrabarti win."
Bennett said that outcome would carry consequences far beyond San Francisco.
"If Chan or Wiener end up winning, it's a clear rejection of the radicalism of the DSA, Justice Democrats, and others who support Chakrabarti," he said. "If that can't win in San Francisco, where can they win exactly?"
Jim Kessler, executive vice president for policy at Third Way, said the district's voters would not be moved by the Pelosi endorsement alone, but that the broader result still points toward the center.
"This is a district where politics is on the menu morning, noon, and night," Kessler told Newsweek. "Voters will be swayed by Pelosi's endorsement, but they'll also make up their own minds because they are hyper-informed. What strikes me about this race is how the most moderate Democratic entry, Scott Wiener, is the most likely winner."
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The succession fight is also unfolding alongside a broader reckoning with Pelosi's legacy—one that goes beyond endorsements and polling.
Since becoming speaker, Pelosi's wealth grew from roughly $30 million to $278 million, the product of well-timed trades in tech stocks and options, and her husband Paul's venture-capital deals, a pattern that fueled public suspicion that lawmakers use insider information to enrich themselves. The family's stock portfolio beat the S&P 500 by nearly 200 percent in 2024.
Pelosi has denied any personal involvement, with her office saying her husband manages the family's investments independently. Newsweek reached out to Pelosi's team for comment on Monday.
However, the controversy has given Chakrabarti one of his sharpest lines of attack, and it has found a receptive audience among younger Democratic voters who see the Pelosi era as synonymous with a party that talks about economic fairness while accumulating personal wealth.
"This is all part of a larger problem, which is just the whole idea of corruption in our politics," he said. "If you're in Congress, you sit on committees that oversee a lot of these industries, and it's unethical to be using that insider information, that knowledge to make stock trades."
What Comes Next
Ross said the deeper issue driving all three candidates, regardless of where they sit on the ideological spectrum, is economic anxiety.
"Voters are very worried about the direction of the economy, particularly with AI, and about their own and their kids' futures," he said. "The Democratic Party needs to be the protector of working people, with a focus on promoting policies and positions that improve people's lives. This is why affordability resonates so strongly—people are squeezed by high prices."
Bennett said that whatever happens in San Francisco, Democrats need to keep their eyes on the bigger map.
"As for the fall, Democrats need to focus on picking up those five House seats in more competitive districts," he said. "Turning blue places bluer, as Chakrabarti wants to do, does nothing to put a check on Trump. Winning red seats does."
Kessler argued that the race may ultimately point in the opposite direction of what many expected from one of the country's most progressive cities.
"At a time when the far left is promising revolution, it is very possible the most mainstream Democrat will take the gold medal," he said, referring to Wiener.
