The year’s biggest political fumbles

Politicians and pontificators are expected to make mistakes from time to time. It’s a peril of the job when constantly going on camera, stepping onstage, talking into a microphone, and tweeting. But there’s a spectrum of error, from a gaffe or unforced self-own to a fatal pattern of misbehavior. Here are some of the silliest slip-ups, biggest blunders, and most career-ending crashes in San Francisco and national politics from an exhausting election year.

Where to begin? Mark Farrell was an early frontrunner in the mayor’s race, only to see his campaign derailed by one report after another about his ethical lapses. It’s almost unfair to suggest the former supervisor and interim mayor was guilty of a “gaffe” when his campaign was hit with the largest ethics fine in San Francisco history a day before the election. But if we had to go with just one face-palm moment, it would probably be the candidate debate in which Farrell said his favorite thing to do in San Francisco is visit Alcatraz. Way to seem normal, man.

When you’re a billionaire, you can afford to change your mind as often as you want. But venture capitalist Ben Horowitz and his wife, Felicia, managed to pull off an embarrassing flip-flop that went viral. The couple stunned their Democrat friends after Ben announced with a16z partner Marc Andreessen that the firm was backing Donald Trump for president. The Horowitzes had been longtime supporters of Democrat candidates and close friends with Kamala Harris, which made the decision mystifying. A story by The Standard scrutinizing the couple’s shift to the right drew a pre-publication rebuke from Ben on X — where, as is his wont, he opened with Kendrick Lamar rap lyrics — only for the couple to jump ship back to Harris in October. To be fair, Felicia’s defensive quote about the chairman of The Standard and reporter Emily Shugerman — “Mike Moritz and Emily Shugerman can kiss the crack of my black ass” — was objectively funny (sorry, Mike and Emily!) and makes the melodrama worth the time wasted.

Speaking of people in tech who should not quote rap lyrics! Garry Tan, CEO of Y Combinator, stepped in it last January when he riffed on a classic 2pac diss track by suggesting San Francisco supervisors should “die slow.” Subbing in elected officials’ names in the lyrics did not go over well, as several progressive supervisors received death threats, and police reports were filed. Tan apologized, and his tweets softened for a short spell before he returned to the social media soap box with a vengeance in the leadup to November’s election.

It might seem like elder abuse to include Joe Biden in this list, but, after all, he’s still the president and leader of the free world. Of course, he should have bowed out many moons before his disastrous debate against Trump. And yeah, introducing Ukraine President Volodymyr Zelensky as “President Putin” at a NATO summit wasn’t great. But Sleepy Joe’s most impactful gaffe came in the home stretch of the election, when he responded to a racist joke by a Trump-supporting comedian by calling Trump supporters “garbage.” It was as if Biden completely forgot what happened to Hillary Clinton in 2016 after her “basket of deplorables” comment. OK, yeah, he probably did forget.

Since his long-sought election victory in 2022 to become supervisor of the Sunset, Joel Engardio has received praise for his policy chops and ability to work with peers and constituents. But in a colossal miscalculation that could cost him his job, Engardio sponsored Proposition K to permanently ban cars from the upper portion of the Great Highway and turn it into a park. He failed to get a full read from residents of his district, and he’s likely to face a recall in 2025 as irritated constituents get set to gather signatures. It’s a rather stunning fall from grace that could shake up the tenuous moderate majority of the Board of Supervisors.

In a year in which every mayoral candidate was desperately courting votes from the Asian American community, Mayor London Breed sparked outrage among Chinatown residents and businesses by announcing plans for a 150-unit sober-living center on Kearny Street. Residents said they weren’t consulted before an announcement was made, leading to an awkward encounter for Breed with cameras rolling. The plan for the center was quickly scrapped, but many voters didn’t forgive or forget, as Breed was denied a second term.

He barely stood a chance of winning the San Francisco mayor’s race, but waiting until just a few weeks before the election to release his first campaign ad didn’t help Supervisor Ahsha Safaí’s chances. He announced his first official campaign ad Oct. 11 — almost a year and a half after revealing his candidacy and 10 days after ballots had been sent to voters. The terming-out supervisor also released a weird video in March that appeared to have the high-res quality of grandpa’s old flip phone. In the tech capital of the world, never go full pixel.

A momentary loss of balance during an official visit to Luxembourg earned the speaker emerita a new hip — and a memorable photo op — this month. But Rep. Nancy Pelosi’s more consequential stumble lay in refusing to admit until far too late what was plain for all to see: Biden had no business running for a second term. In February, Pelosi said the president was “very sharp” and noted that he is younger than her. As a result, Pelosi and Democratic leaders denied the party a chance to hold a real primary and better understand the issues important to voters. While she and venture capitalist Ron Conway were instrumental in eventually pushing Biden off the ticket, it was too little, too late.

Never afraid of a good political brawl, state Sen. Scott Wiener, representing San Francisco, may have finally bitten off more than he can chew. He has refused to back away from principled legislation to create more housing in California and expand LGBTQ+ rights, leading to a near-endless stream of attacks and even death threats. But his effort to push through legislation that would regulate the rapidly accelerating AI industry — drawing opposition from Conway, OpenAI, Meta, and even political ally Breed  — may have irreparably severed political ties with the city’s deep-pocketed tech community. Gov. Gavin Newsom vetoed Wiener’s AI bill, SB 1047, in late September, meaning all that effort went for naught and may leave the senator stranded on a political island as he looks to succeed Pelosi in Congress.