nancy pelosi

As those active in the field will often say, politics is a tough business – it ain’t for everyone. Saikat Chakrabarti, would-be successor to retiring San Francisco Representative and past Speaker of the House Nancy Pelosi, is a recent case in point: a candidate who seemed a perfect fit for the city’s political scene, yet failed to win one of the two slots in the November final. What is unusual about the Chakrabarti story is while we’re all too familiar with political figures who have mastered the art of winning and holding office at the expense of developing a clear vision of why they’re doing it, his problem has largely been the reverse.

Chakrabarti brought two major assets to the race: ideas and money. Some of his past ideas had been quite impactful. After significant involvement in Bernie Sanders’ seminal 2016 presidential campaign, he co-founded Brand New Congress to recruit new congressional candidates, one of whom was Alexandria Ocasio-Cortez. While Brand New Congress proved ephemeral, Justice Democrats, a subsequent organization he also co-founded, has proven to have staying power, continuing to promote Sanders-stripe candidates – with notable successes. Chakrabarti’s money derives from his role as a founding engineer of the then-start-up Stripe, a payments processing company. He is known to be a centimillionaire.