Deportations to Venezuela: Venezuela said it had reached an agreement with the Trump administration to resume accepting deportation flights carrying migrants who were in the United States illegally, with the first one landing as soon as Sunday. Part of Venezuela’s willingness to reverse course after it stopped accepting deportation flights last month appeared related to the plight of Venezuelan migrants the Trump administration recently sent to notorious prisons in El Salvador with little to no due process. Read more ›
Immigrant tax info: The Internal Revenue Service is preparing to help homeland security officials locate immigrants they are trying to deport, according to three officials familiar with the matter, in what would be a shift toward using protected taxpayer information to help President Trump’s mass deportation push. Read more ›
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Retaliation: President Trump broadened his campaign against lawyers he dislikes with a new memorandum that threatens to use government power to punish any law firms that, in his view, unfairly challenge his administration. Read more ›
Heather Knight
Reporting from San Francisco
Nancy Pelosi flicked her hand like she was shooing away a gnat.
She had just been asked whether she was concerned about her new challenger in next year’s election to represent San Francisco in Congress. His name, Saikat Chakrabarti, is unfamiliar to many of the city’s voters. But it’s one that gets under Ms. Pelosi’s skin, given the tense history between the two Democrats going back to his brief and contentious time on Capitol Hill.
“I have them every time,” she said of challengers as she made the hand flick.
Then came an even peskier question. Will this term in Congress — her 20th — be her last?
“I didn’t come here to talk politics,” she snapped. “When I’m in a political arena, I’ll have an answer for you. But that doesn’t worry me one bit.”
Then, turning to members of her staff as they escorted her out of a San Francisco media event, she asked, “Why do they always give women the dumb questions?”
The subject is not as dumb as she might think.
For voters and political insiders in California and beyond, the question of whether she will or she won’t when it comes to her retirement is having a moment. No one knows the answer for certain, but everyone seems to have an opinion on the pros and cons, and the implications, either way.
Ms. Pelosi has been representing San Francisco in Congress for more than 37 years, having first been elected in 1987. Locally, she is not so much a political figure but an era unto herself. She’ll be 86 when her current term expires and has lately been recovering from a December fall, on the marble staircase of a palace in Luxembourg, that required emergency hip replacement surgery.
Her age, her health, the loss of her role as speaker of the House and the generational clashes between her party’s young and elder leaders had led many to anticipate a retirement announcement.
Then along came Mr. Chakrabarti, the metaphorical gnat.
Mr. Chakrabarti is a progressive firebrand who helped pluck Representative Alexandria Ocasio-Cortez out of a job as a New York City bartender and get her elected to Congress. And he has aired sharp criticisms of Ms. Pelosi on social media, alienating much of the elected Democratic Party in the process. He aims to bring the nationwide fight among Democrats over how to combat President Trump home to San Francisco.
“I just realized the Democrats weren’t actually changing at all,” Mr. Chakrabarti said in an interview. “They’re still obsessed with this seniority culture, relying on a backlash to Trump and hoping the pendulum swings back their way.”
In 2018, after Mr. Chakrabarti helped Ms. Ocasio-Cortez win a seat in Congress as her campaign manager, he served as her chief of staff. He soon outraged moderate Democrats in Congress with a storm of social media posts condemning their support of an emergency border funding bill that he said did not fully address conditions in detention centers.
He tweeted that Democrats were “hell bent to do to black and brown people today what the old Southern Democrats did in the 40s.” He also singled out Ms. Pelosi, arguing that she was not willing to talk about the impeachment of Mr. Trump but was also not doing much to help working-class Americans either.
“What is this legislative mastermind doing?” he tweeted.
The comments were considered a huge breach of decorum, and rank-and-file Democrats demanded his ouster as Ms. Ocasio-Cortez moved to make peace with the Democratic caucus. Shortly after a closed-door meeting between Ms. Pelosi and Ms. Ocasio-Cortez, Mr. Chakrabarti left his job.
Mr. Chakrabarti, 39, has plenty of cash to spend. He was the third employee at Stripe, a payment processing company, and has said he’s worth hundreds of millions of dollars and is willing to spend a chunk of his fortune on his campaign.
Ms. Pelosi has filed a statement of candidacy for 2026, a formality that allows her to raise money, but has not explicitly said she will run — or that she will not. Even her closest allies do not know her plans.
Her spokesman declined to comment about her decision on retirement.
Eric Jaye, a longtime San Francisco political consultant who worked on Ms. Pelosi’s first campaign, said that he had no doubt she would beat Mr. Chakrabarti, but also that it would be contentious enough that she might decide to skip it.
“I think she’s going to retire, and it’s a moot point,” Mr. Jaye said. “I seriously doubt she would want her legacy, as stellar as it is, tarnished by having her last race needing to be a knockout, drag-out, negative fight with a representative of the next generation of leaders.”
“I doubt she has any appetite for that,” he continued. “And she has nothing left to prove.”
Drew Hammill, a political strategist who worked for Ms. Pelosi from 2006 to 2023, said he did not know what the former speaker’s plans were but that she would certainly not base her decision on Mr. Chakrabarti’s candidacy.
“The furthest thing from her mind after the weather in the South Pole is this kid,” he said.
But it is possible Ms. Pelosi would be in a tighter race than some political insiders expect.
Interviews with a dozen people on the streets of San Francisco on Thursday showed a range of attitudes toward Ms. Pelosi, from indifference to a desire to see her retire. While several residents said they appreciated her decades of service, they also said they were ready for change.
Nickolas Saldivar, a 44-year-old commercial real estate broker, said he did not feel represented by Ms. Pelosi and her Democratic colleagues in Congress as Mr. Trump dismantles the federal government.
“I think that there’s young blood that needs to come out and that’s going to reinvigorate the party in general,” he said as he stood on Mission Street. “Most of the elected officials, including Pelosi, have been pretty silent on what’s been taking place in D.C.”
Liz Boder, an artist and vendor near the downtown cable car turnaround, said she was “a little bit 50/50 on it” when asked if Ms. Pelosi should retire. She said that the former speaker’s career had been phenomenal but that it might be time for someone new.
“She’s had health issues, and she’s getting a little older, and we might want some fresh perspectives in there,” she said.
Ms. Pelosi visited a San Francisco hospital on Tuesday to discuss the importance of preserving Medicaid amid Mr. Trump’s slashing of the federal budget. She walked slowly, but without the ski poles she had been leaning on until recently. She has ditched her trademark heels for flat, fuzzy clogs.
In addition to her fall, she has dealt with family issues. Her husband, Paul Pelosi, who was viciously attacked in 2022 in the couple’s home by a right-wing conspiracy theorist, recently required a kidney transplant. The organ was donated by their daughter, Jacqueline Pelosi.
In addition to Mr. Chakrabarti’s challenge from the left, Ms. Pelosi would most likely have a deep-pocketed opponent on her right.
David Brailer, the chief health officer of the Cigna Group, a global health insurance company, said he was “strongly considering” entering the race. He declined to discuss details, but a person familiar with his thinking said Mr. Brailer was already conducting polling and was prepared to spend at least $10 million of his own health-care-related fortune on his campaign.
Mr. Brailer is not registered with either party and said he believed voters were tired of both Democrats and Republicans and wanted “pragmatic problem solvers.”
One of the strongest potential challengers for the former speaker would be State Senator Scott Wiener, who has collected nearly $1 million in an exploratory committee to fund a race for the seat he has openly coveted for years. He has won support from a wide variety of voters, including many in the L.G.B.T.Q. community.
But Mr. Wiener has pledged to not run until Ms. Pelosi retires and said he would not run in 2026 if her name was on the ballot. He declined to comment other than to say it would “be an honor” to succeed her.
Another daughter of Ms. Pelosi’s, Christine Pelosi, a lawyer who is active in the Democratic Party, has long been considered a likely heir apparent, although she is staying as tight-lipped as her mother about her own plans.
“My plans are to celebrate Women’s History Month and make sure the 15th anniversary of the Affordable Care Act is not the last!” she texted on Tuesday in response to a request for comment.
Mr. Jaye said he expected Ms. Pelosi to announce her retirement with enough time left in her term to work toward a win for her daughter — or for Mr. Wiener, if her daughter opted not to run.
Whoever is his main challenger, Mr. Chakrabarti said he believed voters were ready to dump traditional, moderate Democrats in favor of progressives.
“I think we’re in an existential moment for the country,” said Mr. Chakrabarti, who worked on Senator Bernie Sanders’s 2016 campaign for president. “How are we going to rebuild from this mess?”
Coral Murphy Marcos and Theodore Schleifer contributed reporting.
Andrew Duehren and Eileen Sullivan
Reporting from Washington
The Internal Revenue Service is preparing to help homeland security officials locate immigrants they are trying to deport, according to three officials familiar with the matter, in a shift toward using protected taxpayer information to help President Trump’s mass deportation push.
Under a draft of an agreement between the I.R.S. and the Immigration and Customs Enforcement, the tax agency would verify whether immigration officials had the right home address for people who have been ordered to leave the United States, according to a copy of the document viewed by The New York Times.
Many undocumented immigrants file tax returns with the I.R.S., giving the agency information about where they live, their families, their employers and their earnings. The I.R.S. has long encouraged undocumented immigrants to pay their taxes, giving people without Social Security numbers a separate nine-digit code called an individual taxpayer identification number to file their returns.
Tax information is closely guarded because federal law bars improper disclosure. I.R.S. officials had resisted earlier requests from the Department of Homeland Security to turn over information about unauthorized immigrants, warning that doing so could violate federal law.
But the Trump administration has since replaced the top I.R.S. lawyer, and the agreement now under discussion appears to be narrower than an earlier request, which asked the I.R.S. to hand over, rather than confirm, migrants’ addresses.
Officials were still finalizing the agreement, the terms of which were earlier reported by The Washington Post. A spokeswoman for the Treasury Department, which oversees the I.R.S., did not respond to a request for comment. ICE also did not respond to a request for comment.
The Department of Homeland Security has repeatedly tried to enlist I.R.S. agents in its broad immigration crackdown, asking them to audit companies that might be hiring unauthorized immigrants.
Shawn McCreesh
Venezuela announced Saturday that it had reached an agreement with the Trump administration to resume accepting deportation flights carrying migrants who were in the United States illegally, with the first one landing as soon as Sunday.
Part of Venezuela’s willingness to accept the flights appeared related to the plight of Venezuelan migrants whom the Trump administration recently sent to notorious prisons in El Salvador with little to no due process. In a statement on Saturday, a representative for the Venezuelan government said: “Migration isn’t a crime, and we will not rest until we achieve the return of all of those in need and rescue our brothers kidnapped in El Salvador.”
The White House did not respond to a request for comment Saturday, though one of the president’s close allies, Richard Grenell, said earlier this month that the Venezuelans had agreed to accept the flights.
Venezuela’s autocratic leader, Nicolás Maduro, suspended the deportation cooperation after the Trump administration revoked a Biden-era policy that allowed more oil to be produced in Venezuela and exported.
Since the suspension of the flights, Mr. Maduro has come under intense pressure from the Trump administration, which has been pressing various Latin American nations to take in more deportees. Secretary of State Marco Rubio said on social media that Venezuela would face new “severe and escalating” sanctions if it refused to accept its repatriated citizens.
Venezuelans have crossed the U.S.-Mexico border in record numbers in recent years, in response to the economic and social crisis consuming the nation, which Mr. Maduro blames on U.S. sanctions against his regime.
The agreement to resume the deportation flights comes after the Trump administration invoked an obscure wartime authority from 1798 called the Alien Enemies Act to deport Venezuelan migrants to El Salvador, whose strongman leader agreed to accept the migrants, putting them in prisons where conditions are so nightmarish that many experts say they constitute human rights abuses.
The use of the wartime authority has emerged as a flashpoint in a broader struggle between federal judges across the country, who have sought to curb many of Mr. Trump’s recent executive actions, and an administration that has come close to openly refusing to comply with judicial orders.
Last week, a federal judge in Washington issued a temporary order blocking the government from deporting any immigrants under the wartime authority, saying he did not believe the law offered grounds for the deportation flights.
The Trump administration had claimed that the Venezuelan migrants who had been sent to El Salvador were all criminal gang members, but the families of some of those men, as well as immigration lawyers, argued that this was not the case for all the deportees sent to El Salvadoran prisons. And the administration provided little detail as to whom the individuals it sent there actually were. There seemed to be little to no due process at play.
Mr. Trump has appeared captivated by the ability to send people to the prison complexes in El Salvador, threatening on Friday that those caught vandalizing Teslas could be banished there for 20 years.
The president and allies, including Elon Musk, went to war with the judge over his order restricting deportations, calling for the judge’s impeachment. The rapidly escalating spat caused Chief Justice John G. Roberts Jr. of the Supreme Court to weigh in with a rare statement, admonishing the calls for the judge’s impeachment. This spurred concerns of a constitutional crisis.
The Trump administration has continued to stonewall the judge’s questions about the deportations to El Salvador. “The government is not being terribly cooperative at this point,” said the judge, James E. Boasberg, at a hearing on Friday. “But I will get to the bottom of whether they violated my order and who was responsible.”
Saturday’s agreement could help Mr. Trump accelerate his plans for mass deportations, one of the central promises of his campaign. He has already enlisted military planes, sent people to third countries far from their homes and invoked the wartime law to achieve that goal. Arrests inside the country are up sharply relative to those in the Biden administration, but they are well below the levels Mr. Trump and his immigration advisers want.
The agreement to resume the deportation flights to Venezuela also comes a day after the Trump administration said that it would end a Biden-era program that allowed hundreds of thousands of people from Cuba, Haiti, Nicaragua and Venezuela to enter the United States lawfully and work for up to two years.
Zolan Kanno-Youngs and Annie Correal contributed reporting.
