Kaylah Williams spends a lot of time with her head in the clouds — literally. Originally from Louisiana, she became a flight attendant four years ago, a decision that coincided with a move to San Francisco. But while she’s well-versed in aircraft etiquette and safety demonstrations, it’s not her prowess as a steward of the skies for which she’s best known. Rather, it’s her whip-smart skills running political campaigns. Last November, she led School Board candidate Alison Collins to victory from out of a field of 18. Now, she’s managing the campaign for district attorney candidate and Public Defender Chesa Boudin.
Williams has always had an eye for politics — she credits her dad, who educated her on key issues as a child. She did her first canvassing at age 15, knocking on doors for former-Senator Mary Landrieu, and was instantly hooked.
So when she moved to the Bay Area with few connections, Williams says she made friends by going “back to the world I feel most comfortable with: community activism and politics.” In the years since, she’s volunteered with Unite Here Local 2, on Bernie Sanders’ presidential run and Jane Kim’s state Senate race. Kim’s 2018 mayoral race was the first time that Williams earned a paycheck in the political sphere.
But it was the School Board race that really gave Williams a chance to shine.
“She’s my mentor and my friend,” she says of Collins. And together, they learned that coalition-building was going to set them apart from the rest.
“We all want to make San Francisco better, so we said, ‘Let’s have your volunteers help our volunteers,’ ” Williams said. “That was the coolest payoff — all the campaigns we worked with won! When you truly work together you really do win together. That made election night so much better.”
It’s nearly impossible to hold a job while running a busy campaign, but Williams is set up perfectly. Her job as a flight attendant provides her with a steady paycheck and health insurance, but also the flexibility to reduce her hours to as little as one or two flights a month. She ramped back up to more flights once the November election passed, but it wasn’t long before another candidate was knocking on her door. This time, it’s a different race entirely: Chesa Boudin, a public defender and the son of two members of Weather Underground, is running for San Francisco District Attorney.
“I was like, ‘I don’t want to do another campaign, I’m exhausted, it was so draining, I’m not sure,’ ” she tells SF Weekly. “Campaign life takes a lot out of you, and I wasn’t sure I wanted to jump in again.”
But then she met Chesa.
“After hearing his story and the things he fights for and the things he stands for I felt so compelled to help,” Williams says. “As a Black woman who has two younger brothers, I know that Black men’s lives are at risk, truly. I should do everything in my power to fight back against this system.”
This is a wildly different race for Williams, but it’s one she’s thrilled to be a part of. It’s the first incumbent-free election for district attorney since 1909, and the city has a unique chance to redefine its values for the local criminal justice system.
“In this campaign there’s a chance for it to get a lot of national attention,” Williams says. “I’m 26 and I think that 20-somethings grew up seeing the real problems our criminal justice system has. Even looking at Kamala Harris — no shade, but she did a lot of things to uphold the status quo. There’s been a lot of pushback. It’s on folks’ minds: What does a district attorney do, and how can someone we vote for be different?”
So Williams is back down to a couple flights a month, and already she’s hit the ground running.
“I feel so excited to take this on,” she says about the campaign. “I was offered the job Friday, I got my wisdom teeth pulled Saturday, and I started Monday.”