Three years after forcing the resignation of their self-described “disrupter” and “asshole” leader, Uber went on to win a major battle in California. Voters in 2020 approved a ballot measure to define Uber drivers and similar gig workers as independent contractors, not employees. The controversial Uber CEO Travis Kalanick was not as indispensable as he thought. Can Republican voters treat Trump the same way?
Arguably, Kalanick’s ruthless and unethical measures were essential to Uber’s success. He fought an entrenched, politically connected taxi industry, a “deep state” of urban transportation. But the excesses piled up over the years: a toxic environment for female workers, who Kalanick dubbed “Boober,” indifference to crimes committed by and against drivers, unwinnable battles against Apple and Google, and a “delete Uber” wave that came after Uber seemed to side against striking New York cab drivers.
The story of Kalanick’s rise and fall was documented in the 2022 season of the Showtime series Super Pumped: The Battle for Uber, which starred Joseph Gordon-Levitt as Kalanick and featured a barely recognizable Uma Thurman as Arianna Huffington, an unlikely mentor who persuades Kalanick to resign. There was no similar figure to “talk down” Donald Trump from his doomed effort to stay President after the 2020 election.
At one point in the show Kalanick admires the loyalty tests Trump demanded of his inner circle but he couldn’t compel similar loyalty: Kalanick’s longtime colleagues would not support his fight to keep his job.

Arguably, Kalanick’s ruthless and unethical measures were essential to Uber’s success. He fought an entrenched, politically connected taxi industry, a “deep state” of urban transportation. But the excesses piled up over the years: a toxic environment for female workers, who Kalanick dubbed “Boober,” indifference to crimes committed by and against drivers, unwinnable battles against Apple and Google, and a “delete Uber” wave that came after Uber seemed to side against striking New York cab drivers.
The story of Kalanick’s rise and fall was documented in the 2022 season of the Showtime series Super Pumped: The Battle for Uber, which starred Joseph Gordon-Levitt as Kalanick and featured a barely recognizable Uma Thurman as Arianna Huffington, an unlikely mentor who persuades Kalanick to resign. There was no similar figure to “talk down” Donald Trump from his doomed effort to stay President after the 2020 election.
At one point in the show Kalanick admires the loyalty tests Trump demanded of his inner circle but he couldn’t compel similar loyalty: Kalanick’s longtime colleagues would not support his fight to keep his job.
