Saikat Chakrabarti picked up the endorsement of Rep. Ilhan Omar on the day of the report, putting one more member of “The Squad” behind his run for Congress in San Francisco as the primary drew within 11 days. Chakrabarti had already announced the support of Rep. Rashida Tlaib on Tuesday, and Alexandria Ocasio-Cortez had still not endorsed him at the time of the report.
The sequence matters because Chakrabarti once spent eight months in 2019 as Ocasio-Cortez’s chief of staff, making her silence a notable gap while two of her closest congressional allies moved in. The report described Omar and Tlaib as members of “The Squad,” and said half of the group was now backing Chakrabarti, a boost he can use as he tries to break through in a crowded race with only days left to make his case.
That support landed in the middle of a sharper fight over how voters see him. One opposing mailer attacked Chakrabarti as a wealthy outsider, saying, “This tech millionaire’s primary residence is in Maryland and he failed to vote in SF for nearly a decade.” It also asked, “Who is Saikat Chakrabarti?” and warned, “Don’t let Maryland Millionaire Saikat Chakrabarti put SF’s Future in Jeopardy!” Chakrabarti has said the Maryland listing was a mistake and that he bought the house for his parents.
He is also trying to turn the attack back on his rivals. A Chakrabarti mailer hit State Sen. Scott Wiener with the line, “Who bought Scott?” and said Chakrabarti “will never take a dime of corporate money — Scott can’t say the same.” The mailer fight has broadened beyond the congressional race to Proposition D, where an anti-mailer carried the words “GUT PUNCH” and said, “We’re just getting the city back on its feet and Prop. D will knock us back down,” while Justin Dolezal argued, “Prop D will fund these services without raising our taxes.”
With the primary 11 days away, the endorsements give Chakrabarti something concrete to point to, but the mailers show the race is still being fought on trust, residency and who can claim to speak for San Francisco. The question now is less whether he can attract attention than whether he can persuade voters that the outside money and outside attacks are the real problem, not his own ties to the city.
