Election extra! Saikat Chakrabarti nabs Rep. Ilhan Omar endorsement, 2nd Squad member to back him

With only 11 days left until the election, most San Francisco mailboxes are filling with new mailers. Amid all the bright colors and chunky fonts — YES ON D! NO ON D! — it takes good design to stand out and avoid the recycling. 

Here’s Mission Local’s round up of the most eye-catching so far. 

Taking the cake is Jeopardy mailer opposing congressional candidate Chakrabarti. On the front page, Chakrabarti glowers at the viewer from behind a television displaying a Jeopardy clue: “This tech millionaire’s primary residence is in Maryland and he failed to vote in SF for nearly a decade.”

“Who is Saikat Chakrabarti?” is the answer, of course. “Don’t let Maryland Millionaire Saikat Chakrabarti put SF’s Future in Jeopardy!” the mailer quips. 

Chakrabarti listed a house in Maryland as his primary residence, but he has said that was a mistake and that he bought the house for his parents. 

And don’t fear — Chakrabarti sent out zinger mailers of his own. One says “Who bought Scott?” with a picture of State Sen. Scott Wiener surrounded by dozens of companies that he’s taken donations from over the course of his years in office. 

The most recognizable corporations are highlighted in red — AirBnB, PG&E, Safeway, Visa, and Amazon, among others. Chakrabarti, it says, “will never take a dime of corporate money — Scott can’t say the same.” 

The other major mailer battle has been over Proposition D, the business tax increase put forward by the city’s unions and opposed by business interests. 

“GUT PUNCH,” one anti-Prop. D mailer says, a red boxer glove bursting out of the page. “We’re just getting the city back on its feet and Prop. D will knock us back down,” it says on the other side. 

The pro-Prop. D mailers haven’t been quite as eye-catching — they have a lot more text. But one features small business owners speaking about how small businesses benefit from well funded city services. “Prop D will fund these services without raising our taxes,” Justin Dolezal, the co-owner of Bar Part Time tells us. 

Read more about the Prop. D fight here. 

Half of the Squad, a progressive quartet of representatives on the Hill, is now backing Chakrabarti for Congress. Today, Chakrabarti unveiled the endorsement of Rep. Ilhan Omar. On Tuesday he announced the support of Rep. Rashida Tlaib. 

But still missing from his endorsements is the nod of Rep. Alexandria Ocasio-Cortez. Chakrabarti was her chief of staff for eight months in 2019. Much has been made of her non-endorsement, but with two other Squad members on board, is hers coming down the pike? 

Read more about Chakrabarti’s tenure on Capitol Hill in a profile of him here. 

Last night was the last campaign finance drop before the primary and the big news was big spending. Chakrabarti’s campaign has reached eight figures — he’s amassed over $10 million, mostly from his own giving. He’s a centimillionaire from his time working for Stripe, a financial technology company. 

He’s been spending furiously to try and make it into the general election, and so has Supervisor Connie Chan — one of those two must make the No. 2 slot to advance. But Chan has far less money. 

Wiener, meanwhile, is likely to make it through and has been saving some of his war chest for November. 

Read the full breakdown of the financial state of the Congress race in our article “Saikat Chakrabarti, Connie Chan spending furiously to secure No. 2 spot in June primary” 

PACs have spent over $1 million trying to keep mayoral allies Alan Wong and Stephen Sherrill on the Board of Supervisors.

In the District 2 race, all the PAC money is behind Sherrill. But in District 4, unions are spending to boost Natalie Gee through a PAC, and another PAC that supports Asian American candidates has put money in for David Lee.

Read more insights about finances in the Board of Supervisor races in our article “Over $4 million pours into S.F. supervisor races, much of it from outside PACs”