San Francisco is bracing for a political transformation as Speaker Emerita Nancy Pelosi, a towering figure in American politics, prepares to step down after nearly four decades representing the city in Congress. Pelosi’s decision not to seek reelection in 2026 has set off the most competitive race for her seat since she first won it in 1987, and the contest is unfolding against the backdrop of both her formidable legislative legacy and recent controversy over her personal finances.
Pelosi, now 85, leaves behind a record that few can match. As reported by LAist, she’s been hailed as “the most effective speaker of the modern era, a legendary political thinker and strategist,” according to Brian Hanlon, co-founder and CEO of California YIMBY. Pelosi’s leadership saw the passage of landmark legislation such as the Affordable Care Act, and she became known for her sharp critique of former President Donald Trump. Her influence extended far beyond the city’s borders, making San Francisco a political heavyweight on the national stage.
With Pelosi’s seat up for grabs, three distinct candidates have emerged as frontrunners, each offering voters a different vision for the city’s future. Connie Chan, the 47-year-old San Francisco supervisor for District 1, is leaning on her immigrant background and local experience. Born in Hong Kong, Chan immigrated to the U.S. as a teenager and has made her personal journey central to her campaign. “As a first-generation immigrant, I have the lived experience, understanding the challenges that immigrant community faces, and most definitely during this time, when we see the Trump administration sending ICE agents to our streets and also in courtroom, firing our immigration court judges so that they can detain our immigrants illegally,” Chan told KQED. She’s currently in her second term on the Board of Supervisors and has taken stances against denser housing proposals and certain park initiatives, positioning herself as a defender of neighborhood character and local control.
Scott Wiener, a 55-year-old state senator, is well-known for his legislative prowess and advocacy for housing reform. According to LAist, Wiener has passed 12 bills in 2025 alone and was ranked the most effective California State Senator by the nonpartisan Center for Effective Lawmaking. Wiener is openly gay and would be the first openly gay representative from San Francisco in the House—something he says is long overdue. His campaign is fueled by a belief in the city’s LGBTQ+ legacy and a determination to address housing shortages through bold state-level policies, though these positions have generated both support and criticism locally.
The third major contender, Saikat Chakrabarti, brings a different kind of outsider energy. At 39, Chakrabarti has already made millions as one of the first software engineers at Stripe and has a notable political resume, having worked on Bernie Sanders’ 2016 presidential campaign and served as chief of staff to Rep. Alexandria Ocasio-Cortez. He’s positioning himself as the candidate most willing to challenge the Democratic establishment. “I think I’m the only one willing to challenge the Democratic party establishment,” Chakrabarti told KQED. “People know that the Democratic party needs a new direction, it needs new ideas and it needs solutions that are as big as the problems that we face. And that’s what I’m offering the voters.”
While each candidate brings a unique perspective, certain issues dominate the race. Housing affordability is front and center, with Chan criticizing Wiener’s “Sacramento version of affordable housing” and Chakrabarti supporting controversial new developments like the proposed 800 units above a Safeway in the Marina. All three candidates have pledged to resist Trump-era immigration policies, including ICE raids and mass deportations, reflecting the district’s progressive values.
Foreign policy has also crept into the local debate, particularly U.S. military funding for Israel amid ongoing conflict in Gaza. Wiener, who is Jewish, has spoken out against antisemitism while trying to balance support for Israel’s existence with criticism of its war conduct. Chakrabarti has made Palestinian rights a central issue, stating, “I’m opposed to military funding in Israel as long as the genocide continues.” Chan has echoed similar concerns, saying she would not support sending “weapons of war” to Israel and calling the situation in Gaza a human rights violation that meets the legal definition of genocide.
Money and endorsements are, as always, crucial. Chakrabarti, despite being the least known, has significant wealth to self-fund his campaign and touts his behind-the-scenes work on the Green New Deal. Chan may face fundraising hurdles but has local union support, notably from Unite Here Local 2. Wiener, meanwhile, has been preparing for this run for years, having raised over $1 million by September 2025, with fundraising reportedly accelerating after Pelosi’s retirement announcement.
Pelosi’s own influence, even in retirement, looms large. While she hasn’t officially endorsed a successor, she appears most closely aligned with Chan, having appeared with her at recent events. The San Francisco Democratic Party’s endorsement could be a game-changer, but as local party chair Nancy Tung told KQED, “It’s within the realm of possibility that Scott Wiener would actually get the endorsement. I think he’s probably got the best chance.”
This high-stakes race is unfolding amid renewed scrutiny of Pelosi’s personal finances. On December 20, 2025, Republican Congresswoman Anna Paulina Luna accused Pelosi of insider trading, citing her nearly 17,000% returns on stock investments—a performance that has outpaced even Warren Buffett. Luna declared at Turning Point USA’s AmericaFest, “Nancy Pelosi, by the time that she announced that she was no longer seeking office, had outperformed Warren Buffett. We’ve nicknamed her the REAL ‘Wolf of Wall Street.’ She's currently outperformed the S&P and made over 17,000% returns on her stock investment. That statistically does not happen unless you are engaged in insider trading.”
Such allegations are not new. In November, Republican National Committee spokesperson Kiersten Pels remarked, “Nancy Pelosi’s true legacy is becoming the most successful insider trader in American history. If anyone else had turned $785,000 into $133.7 million with better returns than Warren Buffett, they’d be retiring behind bars.” According to the New York Post, the Pelosis’ initial stock portfolio, valued between $610,000 and $785,000 in 1987, has grown to approximately $133.7 million by November 2025. Their holdings include shares in Alphabet, Apple, Broadcom, Microsoft, Netflix, Nvidia, Palo Alto Networks, Salesforce, and Tempus AI. In 2024 alone, their portfolio reportedly gained 54% returns—double the S&P 500’s 25%—and the couple’s combined net worth now stands at $280 million, up from $3 million in 1987. Their real estate assets include an $8.7 million home in San Francisco’s Pacific Heights and a valuable flat in Washington DC’s Georgetown.
Pelosi’s office has not responded to requests for comment on these allegations, and to date, no formal charges have been brought against her. Still, the controversy adds a layer of complexity to the race for her successor, as voters weigh not just policy positions but questions of character and legacy.
With the June 2026 primary fast approaching, San Francisco’s voters face a consequential choice. The top two candidates will move on to the November general election, shaping the city’s—and perhaps the nation’s—political future. Whoever wins will inherit not just a seat in Congress, but the daunting task of following in Pelosi’s formidable footsteps, amid both the promise of renewal and the shadow of controversy.
