When Fergie Chambers, the wayward son of the Cox media dynasty, decamped to Tunisia at the end of 2023, he must have known he would return to America someday, but this is probably not how he imagined it. He might have pictured himself like Lenin, shuttled across the border in a sealed railroad car at the height of a revolution. Or like Khomeini, summoned from exile in the wake of a triumphant rebellion. Instead, he sits in a Spanish prison, fighting an extradition request that could send him home in handcuffs to face charges of laundering money the U.S. government says went to Hamas.

Chambers is a trust-fund revolutionary with unusually deep pockets. In 2023, he agreed to sell his stake in his family’s company in a deal worth at least $250 million, according to Rolling Stone. He is married to the actress Stella Schnabel, daughter of the artist and filmmaker Julian Schnabel, and his fight against extradition has attracted some well-known supporters: Richard Gere, Cynthia Nixon, Viggo Mortensen, and Greta Thunberg are among those who have signed a letter urging Spain to reject the American request.