The CEO who brokered the worst deal in history

Gerald Levin 1939–2024

In January 2000, Gerald Levin was riding a winning streak. In the 1970s, he’d helped turn a fledgling cable channel called Home Box Office into a pay-per-view giant. At Time Inc., the so-called resident genius had overseen a 1990 merger with Warner Communications to make the world’s largest entertainment company. As Time Warner CEO, he’d bought Turner Broadcasting, acquiring CNN. Now he was spearheading the biggest deal in history: a $165 billion merger of Time Warner and America Online. Joining the old-media juggernaut to the world’s top internet company would build a media colossus for “the internet century,” he said. Instead, it was the biggest flop in corporate history. The internet bubble burst, AOL’s pokey dial-up service was eclipsed by broadband, and AOL was charged with wildly inflating its premerger profits. In 2002, AOL Time Warner lost nearly $100 billion, still a record. “I’m very sorry about the pain and suffering and loss that was caused,” Levin said in 2010. “I presided over the worst deal of the century, apparently.”

Levin was born in Philadelphia, where his father ran a grocery business, said The Washington Post. He studied biblical literature and philosophy at

Haverford College, then earned a law degree at the University of Pennsylvania. After doing development work in Iran and Colombia, he took a job at a New York cable company developing “a pay-for-programming concept for movies and sports,” soon named Home Box Office. His seminal moment came when he persuaded parent company Time to transmit HBO’s signal by satellite, an industry first. “His gamble paid off spectacularly,” said the Financial Times, when the new network delivered the legendary “Thrilla in Manila” prizefight between Muhammad Ali and Joe Frazier live to subscribers—a success that paved the way for the cable revolution. With that triumph, Levin found his “career transformed overnight.”

Amid “plummeting internet stock values” after his record loss, Levin left Time Warner, said Bloomberg. Marrying his third wife in 2003, he helped her open an upscale holistic health center in Santa Monica, Calif. After he was diagnosed with Parkinson’s in 2006, the pair opened a center to help patients with the condition. He made no excuses for the merger debacle, acknowledging his culpability as CEO. “It’s just a stunning piece of history,” he said. “I invite business schools to continue to study it.”