Gerald Levin, the former CEO of Time Warner Media, passed away at the age of 84 in San Francisco on Wednesday. Levin, who had been diagnosed with Parkinson's disease, was known for leading the company into a disastrous $182 billion merger with America Online in 2000. Levin's career at Time Warner started in the early 1970s, when he joined the company as it transitioned from print magazines to cable television. He played a key role in the success of HBO, convincing Time brass to invest in satellite distribution, which allowed the company to broadcast major events like the boxing match between Muhammad Ali and Joe Frazier in 1975. Levin's strategic thinking and negotiation skills led to the merger between Time and Warner Bros. in 1987, and eventually to the ill-fated merger with AOL. Despite initial success, the AOL-Time Warner merger was plagued by internal conflicts and the bursting of the dot-com bubble, leading to Levin's resignation in 2001. The merger was unwound in 2009, with Time Warner dropping “AOL” from its name. Levin's legacy is a mixed one, with his early successes overshadowed by the failure of the AOL merger. His career serves as a cautionary tale of the risks of overlooking emerging technologies and the importance of strategic planning in the ever-changing media landscape.