The political landscape in San Francisco is witnessing a shift as Saikat Chakrabarti, Alexandria Ocasio-Cortez’s former chief of staff, campaigns to succeed Representative Nancy Pelosi. Pelosi, who is retiring, has endorsed another candidate, Connie Chan, a left-wing San Francisco supervisor.

Chakrabarti, a Democrat known for his progressive views, highlights his previous role with Ocasio-Cortez to bolster his anti-establishment campaign. His public appearances are often accompanied by a mobile billboard with the claim “A.O.C. FIRED SAIKAT,” illustrating a complicated relationship with the congresswoman.

Despite his efforts, Ocasio-Cortez has not mentioned Chakrabarti in her endorsements or campaigns, instead supporting other left-wing candidates across the country, including in Philadelphia and Montana.

The rivalry intensifies as the primary approaches on June 2. Chakrabarti faces stiff competition from both Chan and State Senator Scott Wiener. Current polls indicate a tight race for the second-place spot between Chakrabarti and Chan, with Wiener in the lead.

Chakrabarti played a vital role as campaign manager during Ocasio-Cortez’s first congressional run in 2018, furthering his reputation as a key strategist. This background is central to his current bid for Congress in the San Francisco district.

As the race progresses, the outcome remains uncertain, with Chakrabarti’s previous association with Ocasio-Cortez both a significant talking point and a point of contention among voters.