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nancy pelosi
The Cautionary Tale of Saikat Chakrabarti
The campaign did not turn out as hoped for the individual who helped catapult Alexandria Ocasio-Cortez into Congress and co-founded Justice Democrats.
Jun 09, 2026
As those active in the field will often say, politics is a tough business – it ain’t for everyone. Saikat Chakrabarti, would-be successor to retiring San Francisco Representative and past Speaker of the House Nancy Pelosi, is a recent case in point: a candidate who seemed a perfect fit for the city’s political scene, yet failed to win one of the two slots in the November final. What is unusual about the Chakrabarti story is while we’re all too familiar with political figures who have mastered the art of winning and holding office at the expense of developing a clear vision of why they’re doing it, his problem has largely been the reverse.
Chakrabarti brought two major assets to the race: ideas and money. Some of his past ideas had been quite impactful. After significant involvement in Bernie Sanders’ seminal 2016 presidential campaign, he co-founded Brand New Congress to recruit new congressional candidates, one of whom was Alexandria Ocasio-Cortez. While Brand New Congress proved ephemeral, Justice Democrats, a subsequent organization he also co-founded, has proven to have staying power, continuing to promote Sanders-stripe candidates – with notable successes. Chakrabarti’s money derives from his role as a founding engineer of the then-start-up Stripe, a payments processing company. He is known to be a centimillionaire.
The connection with Ocasio-Cortez went on to became substantial, as he served as her campaign manager, chief of staff following her 2018 upset election to Congress, and a principal in the formulation of the Green New Deal legislation that she introduced in the House. Unfortunately, Chakrabarti himself did not fare so well within the walls of the House as he had without. He soon drew fire within the Democratic Caucus for sending out tweets criticizing other House members by name. Although he had previously shown great facility in dealing with both “big picture” political questions as well as the mechanics of campaigning, the curriculum doesn’t stop there. What he had apparently failed to understand was that while members of Congress may choose to criticize their colleagues by name, their staff are not expected to do so without the approval of the elected representative. Before her first year in office was out, he and Ocasio-Cortez would part ways. He went on to work on Green New Deal-type issues in an outside organization. Neither would subsequently speak in great detail about the parting. She did not endorse his congressional run.
In October 2025, Chakrabarti formally announced his candidacy for the San Francisco congressional seat. It was widely expected that the Speaker Emerita would not be running for re-election, but then she had surprised many by running for the term she was now serving after losing the speakership to the Republicans and stepping down from party leadership – and had made no statement regarding her 2026 intentions. Chakrabarti’s move forced the hand of State Senator Scott Wiener whose desire to succeed Pelosi was well known. (It had also previously been widely assumed that when Wiener did run he would ultimately get the nod of the Pelosi-Willie Brown establishment wing of the party, something that did not happen, presumably in part due to his announcing for the seat before Pelosi indicated her intention to leave it.)
To one unfamiliar with the details of San Francisco politics the Chakrabarti candidacy would likely have seemed a welcome development for the a left that has long been frustrated by city’s domination by what they considered the corporate-oriented wing of the Democratic Party – here was a big picture candidate with the capacity to run a high budget campaign. (Chakrabarti put in something like $10 million of his own money over the course of the campaign.) And he even seemed to recognize the fundamental truth that the wealthy will generally deny to their dying days – that all value comes from labor, telling supporters at his kick-off rally, “I ended up making a lot of money, and that was a profoundly weird and radicalizing experience,” but “I did not work harder than my teacher or a nurse or the people cleaning our offices ...I just won the startup lottery.”
But the campaign did not turn out as hoped. At the time of this writing the latest tally shows him at 17 percent, trailing Weiner at 41 percent and Supervisor Connie Chan at 29 percent. Chan, who much of the city’s left ultimately rallied around, might never have run if Chakrabarti had actually proved to be that hoped-for candidate. So what went wrong? Well, for one thing it wasn’t that his potential base refused to vote for a wealthy candidate who appeared to be trying to buy the office. Billionaire gubernatorial candidate Tom Steyer, who spent over $200 million on his race, carried San Francisco by a 38-25 percent margin over statewide frontrunner Xavier Becerra, the voters apparently deciding that he been putting his ill-gotten gains to good use.
A San Francisco Chronicle post mortem maintained that Chakrabarti’s problem was that he didn’t meet the right people. An article painting the city’s politics as special – which they are, just like every other city’s politics are special – described “San Francisco’s bare-knuckled political scene that is famously described as a ‘knife-fight in a phone booth’” to which “San Francisco Democratic Party Chair Nancy Tung added a telling detail ... ‘It’s a knife fight in a phone booth where you know everybody in the phone booth.’” The article goes on to say that, “Chakrabarti didn’t reach out to Tung,” and “More surprisingly, he didn’t reach out to [former Supervisor Aaron] Peskin, who is deeply wired into the city’s left.” Here the Chronicle ever so slightly touches on the real story, one that was covered by the city’s online publications, particularly 48 Hills and Mission Local.
Unmentioned in the Chronicle article is the fact that Peskin had been the candidate of the left in the city’s 2024 mayoral election and not only did Chakrabarti fail to meet Peskin, but he supported his opponent, the winner and current mayor Daniel Lurie (who has just successfully led the opposition to a ballot question proposing an increase to the rate and scope of the city’s Overpaid Executive Tax that is levied on companies with executives making more than 100 times the median employee compensation.) Perhaps even more importantly though, Chakrabarti also supported the candidate who supplanted Dean Preston on the city’s Board of Supervisors. Preston, a member of the Democratic Socialists of America, had been the city’s elected official most prominently championing the type of politics that Chakrabarti proclaimed that he was all about. And not just did he support Bilal Mahmood against Preston in 2024, but he donated to his campaign funds – plural because while contributions to supervisorial races are limited to $500, candidates can and often do simultaneously run campaigns for the Democratic County Central Committee, a race run without that contribution limit – the money spent on one race obviously redounding to the benefit of both. Chakrabarti contributed not only the maximum $500 to Mahmood’s supervisorial campaign, but also an additional $10,000 to his successful DCCC campaign in which he ran on what 48 Hills called “the right-wing corporate slate that took over the local Democratic Party” – ironically the same one that Party Chair Nancy Tung ran on.
It’s an unfortunate story really. The tangle of policy, principle, friendship, relationships, and future prospects that may go into endorsement decisions can be a thorny matter for anyone involved in politics, but in this case the opposition to Preston was really not a close question. For many it was simply disqualifying – after all, if he was off on this, what else might he be off on? Absent such egregious errors Chakrabarti might have been the candidate the San Francisco left was hoping for; he was talking a more radical talk than Chan does. Hopefully he’ll go on to make further useful policy contributions. Who knows maybe he’ll even try the electoral route again some time. But if he does, maybe he will have learned by then that there’s more to it than just knowing which way you’d vote on the big bills. Politics is a tough business – it ain’t for everyone.
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'Long-Overdue': Pelosi to Retire After Four Decades in Congress
Pelosi's progressive challenger called it the start of a "generational shift" in the Democratic Party.
Nov 06, 2025
Former House Speaker Nancy Pelosi is calling it quits after nearly four decades in Congress. On Thursday, the longtime Democratic leader announced that her 20th term in Congress will be her last and that she will not run for reelection in 2026.
"For decades, I've cherished the privilege of representing our magnificent city in the United States Congress," Pelosi (D-Calif.) said in a video tribute to her constituents in San Francisco. "That is why I want you, my fellow San Franciscans, to be the first to know I will not be seeking reelection to Congress. With a grateful heart, I look forward to my final year of service as your proud representative."
The departure of the 85-year-old Pelosi, the first and only woman to ever hold the speaker's gavel, comes at a critical crossroads for the Democratic Party, when the brand of corporate-friendly centrism she came to embody faces a crisis of credibility after failing to withstand the return of President Donald Trump, and an increasingly muscular progressive flank seeks to reshape the party in its image.
"Starting out as a progressive, Pelosi has steadily drifted to the center over the decades, coinciding with her rise up the party ranks, the gradual rise of her net worth, and even San Francisco’s transformation into an unaffordable playground for the rich," wrote Branko Marcetic in Jacobin when she stepped down from the role as the Democratic leader in 2022.
Once a proponent of universal healthcare, Pelosi will likely be remembered as one of the foremost obstacles to achieving Medicare for All, which she fought tooth and nail to block, with the support of the health insurance industry, during her final four years as speaker.
As the climate crisis grows more urgent and increasingly destructive, Pelosi will be remembered as the person who derided the nascent "Green New Deal" effort to transition America's economy toward renewables as "the green dream or whatever they call it."
As the Democratic Party's base reckons with its near-total shift against Israel following more than two years of genocide in Gaza, Pelosi—who previously backed funding for the Iraq War against the grassroots of her party—will be remembered as the person who, suggested that Democrats protesting for a ceasefire were spreading “[Russian President Vladimir] Putin’s message” and should be investigated by the FBI.
As Immigration and Customs Enforcement (ICE) rampages through American cities—including her beloved San Francisco—tormenting immigrants and citizens alike, Pelosi will be remembered for her role bending to Republican demands during the last government shutdown in 2019, to hand the agency more funding as part of a power play against the progressive "Squad" members who wanted to see the agency abolished or defunded.
And at a time when Americans struggle with a surging cost of living, Pelosi will be remembered as one of the people who profited most from her position at the heights of power. In 2024, she and her husband raked in more than $38 million from stock trading, more than any other member of Congress in either party, and remained a persistent defender of the humble elected representative's right to use their immense wealth of insider knowledge for personal gain.
Pelosi's retirement announcement comes at a moment when the Democratic establishment, particularly its congressional leaders—Senate Minority Leader Chuck Schumer (D-NY) and Pelosi's successor, House Minority Leader Hakeem Jeffries (D-NY)—face historic unpopularity with their own voters.
A survey published by Pew Research at the beginning of October found that 59% of self-identified Democrats disapprove of the job their leaders are doing. A previous poll from Reuters/Ipsos found that Democrats believe there was a large gulf between their governing priorities, like universal healthcare, affordable childcare, and higher taxes on the rich, and those of the party.
Pelosi's announcement comes just two days after the most significant triumph in decades for the progressive movement she tried to crush, with the democratic socialist state assemblyman Zohran Mamdani being comfortably elected as New York City's next mayor despite Pelosi's refusal to endorse.
"This is an appropriate response to Mamdani’s win," New Republic writer Indigo Oliver said of Pelosi's retirement on social media. "Chuck Schumer should follow Pelosi’s lead."
Even prior to her retirement becoming official, momentum was building behind a more progressive candidate to take Pelosi's seat as well: Saikat Chakrabarti, the former chief of staff for Rep. Alexandria Ocasio-Cortez (D-NY), who some have described as a "clone" of Mamdani, though he too has been met with criticism for his coziness with San Francisco's powerful tech sector.
"Pelosi’s retirement marks the end of an era in San Francisco politics and the beginning of a long-overdue generational shift," said an email from the Chakrabarti campaign.
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Senate Advances Bill Banning Politicians From Stock Trading—While Giving Trump a Big Carveout
"Voters have a right to know that their elected representatives are acting in the public's best interest and are not motivated by their personal financial interests," said the general counsel at the Campaign Legal Center.
Jul 30, 2025
The Senate Homeland Security and Governmental Affairs Committee on Wednesday narrowly voted in favor of advancing a bill that bars politicians at the federal level from trading stocks—with one highly notable exception.
As reported by Politico, Sen. Josh Hawley (R-Mo.) joined with all Democrats on the committee to advance a bill to ban stock trading by elected officials. However, to get Hawley's vote, Democrats had to agree to create a carveout for U.S. President Donald Trump and to apply the stock-trading ban only to future presidents.
Business Insider reported that, as written, the legislation "would ban members of members of Congress, the president, and the vice president from buying stocks immediately upon enactment, and would block them from selling stocks beginning 90 days after that."
"It would then require lawmakers to divest entirely from their stock holdings at the beginning of their next term, and it would require the president and vice president to do so beginning in 2029—after President Donald Trump's current term," the outlet explained.
Hawley took heat from fellow Republicans on the committee for advancing the legislation, including Sen. Rick Scott (R-Fla.), who accused his Missouri colleague of demonizing the wealthy.
"I don't know when in this country it became a negative to make money," said Scott. "How many of you don’t want to make money? Anybody want to be poor?"
Sen. Elissa Slotkin (D-Mich.) said that she wished that the law didn't have a carveout for Trump, but nonetheless supported advancing the bill and she described herself as "willing to make the good work instead of waiting for the perfect."
The bill's advancement out of committee earned plaudits from some government reform advocates. Craig Holman, a government affairs lobbyist with Public Citizen, encouraged the full U.S. Senate to take up a vote on the package while also explaining the proposed legislation's importance.
"Members of Congress frequently have access to nonpublic information about economic and business trends and are in a position of power to influence those trends," he said. "That is why the American public—Republicans, Democrats and Independents alike—has called for this type of legislation ever since a series of insider trading scandals erupted over the last several years."
Kedric Payne, the vice president and general counsel at the Campaign Legal Center (CLC), similarly praised the bill's advancement while also explaining why current transparency rules were no longer adequate.
"To prevent corruption and conflicts of interest, CLC has long called on Congress to update the STOCK Act, which merely requires members to disclose their transactions, and fully ban stock trading by sitting legislators," said Payne. "In the absence of these stronger rules, we've seen congressional stock trading proliferate. This has led to repeated examples of ethical violations and questionable financial activity, including during global health emergencies and times of great economic uncertainty."
Payne further emphasized that "voters have a right to know that their elected representatives are acting in the public's best interest and are not motivated by their personal financial interests."
The legislation advanced by Hawley and the Democrats was originally named after Rep. Nancy Pelosi (D-Calif.), the former speaker whose highly profitable stock trades have come under scrutiny in recent years.
Even though the bill has now made its way out of committee, it still faces an uncertain future in the full U.S. Senate where Republicans currently hold a 53-47 majority and where Democrats would need to win over some additional Republican converts on top of Hawley. And even should it pass the Senate, it's uncertain whether the legislation would be able to pass the Republican-controlled House of Representatives.
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