Saikat Chakrabarti unveiled the endorsement of Rep. Ilhan Omar on the day the article was published, giving his campaign another boost as the primary entered its final 11 days. Omar became the second member of “The Squad” to back Chakrabarti after Rep. Rashida Tlaib announced her support on Tuesday.
The new endorsement gives Chakrabarti a fresh line of attack in a race where he has tried to present himself as the progressive choice. He worked as Alexandria Ocasio-Cortez’s chief of staff for eight months in 2019, and his campaign has been trying to turn that biography into a governing argument as voters narrow their choices.
Much has been made of Ocasio-Cortez’s decision not to endorse him. That silence has shadowed Chakrabarti’s campaign even as he has collected support from two members of the bloc associated with her. By the time Omar’s endorsement landed, campaign finance filings had already dropped the night before, adding another layer of scrutiny to a contest that has become as much about money and identity as about ideology.
One of the sharpest flashpoints has been Chakrabarti’s own residency. He listed a house in Maryland as his primary residence, then said that was a mistake and that he had bought the house for his parents. The issue has fed into a broader effort by opponents to portray him as out of step with the city he is trying to represent, even as his allies argue that the race should turn on policy and turnout, not paperwork.
The mailers circulating around the contest have only deepened the split-screen nature of the campaign. An opposing piece warned, “Don’t let Maryland Millionaire Saikat Chakrabarti put SF’s Future in Jeopardy!” while one of Chakrabarti’s own mailers asked, “Who bought Scott?” and attacked State Sen. Scott Wiener for taking donations from companies including AirBnB, PG&E, Safeway, Visa and Amazon. In another line of attack, Chakrabarti’s campaign said it “will never take a dime of corporate money — Scott can’t say the same.”
The fight is not happening in a vacuum. Separate campaign messaging around Proposition D has also sharpened the tone in the final stretch, with Justin Dolezal arguing, “Prop D will fund these services without raising our taxes.” The result is a citywide argument over money, outside influence and trust, with four neighborhoods, four dedicated reporters and 11 days left for voters to sort through the noise.
That leaves Chakrabarti with a clear but narrow path: he has the endorsements, but he still has to prove that late momentum can outweigh the doubts about where he lives and whether his campaign’s anti-corporate message can survive a race defined by competing mailers and an unanswered question from Ocasio-Cortez’s camp.
