Top 10 Most Controversial Business Leaders

Bet $36 billion on the metaverse pivot, weathered congressional hearings over teen mental health, and reshaped Facebook's content moderation policies amid global censorship debates.

Built Uber into a global juggernaut through scorched-earth tactics, regulatory defiance, and a toxic workplace culture that ultimately forced his resignation as CEO.

Inflated WeWork's valuation to $47 billion on charisma and kombucha, then watched it collapse by 80% before IPO — only to receive a $245 million exit package.

PayPal co-founder turned controversial venture capitalist who secretly funded the lawsuit that destroyed Gawker Media and has backed disruptive political campaigns worldwide.

Alibaba's charismatic founder publicly criticized Chinese financial regulators in 2020 and subsequently vanished from public view as Beijing launched an antitrust crackdown on his empire.

The youngest self-made female billionaire became a convicted felon after Theranos defrauded investors and endangered patients with unreliable blood tests.

Led Activision Blizzard through years of workplace harassment scandals and regulatory scrutiny before the controversial $69 billion Microsoft acquisition closed.

SoftBank's visionary lost $17 billion on WeWork and other bets from the Vision Fund, yet continues placing massive wagers on AI with unwavering conviction.

The Nissan-Renault chief was arrested in Japan for financial misconduct and then orchestrated a Hollywood-worthy escape hidden inside a musical equipment box to Lebanon.

Bet $36 billion on the metaverse pivot, weathered congressional hearings over teen mental health, and reshaped Facebook's content moderation policies amid global censorship debates.

Built Uber into a global juggernaut through scorched-earth tactics, regulatory defiance, and a toxic workplace culture that ultimately forced his resignation as CEO.

Inflated WeWork's valuation to $47 billion on charisma and kombucha, then watched it collapse by 80% before IPO — only to receive a $245 million exit package.

PayPal co-founder turned controversial venture capitalist who secretly funded the lawsuit that destroyed Gawker Media and has backed disruptive political campaigns worldwide.

Alibaba's charismatic founder publicly criticized Chinese financial regulators in 2020 and subsequently vanished from public view as Beijing launched an antitrust crackdown on his empire.

The youngest self-made female billionaire became a convicted felon after Theranos defrauded investors and endangered patients with unreliable blood tests.

Led Activision Blizzard through years of workplace harassment scandals and regulatory scrutiny before the controversial $69 billion Microsoft acquisition closed.

SoftBank's visionary lost $17 billion on WeWork and other bets from the Vision Fund, yet continues placing massive wagers on AI with unwavering conviction.

The Nissan-Renault chief was arrested in Japan for financial misconduct and then orchestrated a Hollywood-worthy escape hidden inside a musical equipment box to Lebanon.