Gerald Levin, known to many as Jerry, wasn’t flamboyant. He wasn’t characterized, as were many of his media business contemporaries, by extravagant hobbies, odd peccadillos, inspiring speeches or a spicy personal life. He could be testy. But he didn’t engage in public brawls beloved by – and between – Ted Turner and Rupert Murdoch.

Levin, who died Wednesday at 84 nearly two decades after being diagnosed with Parkinson’s disease, was a philosophy major at Haverford College who was said to be fond of quoting Camus. But he was also private and often enigmatic at a time when the industry was led by brash founder-leaders like Viacom’s Sumner Redstone and News Corp.’s Murdoch. Michael Eisner was not a founder but a big personality. Bob Iger has been called a CEO out of central casting. “Jerry Levin was not your central casting CEO,” noted one Wall Streeter.

Levin, a lawyer-turned-executive who had a steady rise up the corporate ladder, ended up making a bigger public splash than any of his peers at the turn of the millennium by merging Time Warner with AOL. In a sense, the combination was visionary. He realized that the internet was the future of media. And AOL was internet behemoth of the moment, teeing things up for a deal valued at $350 billion deal, still the biggest in U.S. corporate history. Levin and AOL chief Steve Case added a puckish touch at a news conference unveiling the deal, with the conservatively dressed Levin ditching his necktie and the tech-bred Case donning neckwear. Worlds had collided, the message said.

All of the image-managing and blue-skying would be for naught. The deal became a disaster, destroying billions of dollars of shareholder value and vaporizing employee stock options.

In hindsight, the timing of the deal, which was conceived in 2000 and closed in early 2001, was ill-starred. It came at the tail end of a dotcom bubble that had been sending internet stocks to the moon since 1995. Valuations had exploded, which explains why AOL at the time was worth more than Time Warner. The deal was billed as a merger of equals, but AOL bought Time Warner with a 55% controlling interest.

It’s never clear exactly when a bubble will pop. Investors decided to overlook all the red ink, predicting dotcoms would upend all business sectors, especially media. They kept piling into all kinds of companies until eventually the music stopped. In March 2000, the Nasdaq peaked. Interest rates rose. There was a recession in Japan. Capital stopped flowing, and profitability became key (again an eerie precursor of the streaming era).

Consumers also started moving from dial-up to broadband. AOL, which was rooted in dial-up, started to lose more and more subscribers every quarter (a secular decline echoed today by pay-TV cord-cutting).

Operationally, the merger also wasn’t really given a chance.

Neither Time Warner Cable nor Road Runner broadband, both owned by AOL Time Warner, made AOL their default platform or made AOL a priority. So it couldn’t grow, only shrink. The famously insular fiefdoms of Time Inc., Warner Bros., CNN and HBO executed the mirror opposite of a Disney-style synergy blitz. Resentments grew. Cultures clashed. An investigation by federal regulators on AOL improperly inflating advertising revenue resulted in the parent company having to restate earnings, which didn’t help intramural relations. Lawsuits ensued, then layoffs and a revolving door in the executive suite. It’s not at all clear that the merger would ever have been a resounding success, but it never got the internal buy-in that might have at least forestalled the inevitable for a bit longer.

Levin ended up stepping down in 2002. Case, who founded AOL and served as chairman of AOL Time Warner, exited in 2003. Richard Parsons ran the company as CEO through 2007. Jeff Bewkes took the helm after Parsons, and formally unwound the merger in 2009, leading to the classic picture of workers removing the ‘AOL’ letters from atop New York’s Time Warner Center. Bewkes then set about streamlining company to be sold, which it finally was in 2018 to AT&T.

Investors lost big on AOL Time Warner, none more than Ted Turner, who had become a major shareholder in Time Warner after selling his Turner Broadcasting to Time Warner in 1995. He was then marginalized from the company and has said he lost 80% of his wealth in the AOL merger.

The media industry overall had gotten swept up in merger mania as the dotcom bubble had them destabilized – in many ways a precursor to the mania around streaming that has wreaked havoc in the current decade. AOL-Time Warner happened at around the same time that Sumner Redstone merged CBS and Viacom, and Universal Studios parent Seagram sold itself to French conglomerate Vivendi, and both of those combinations would also soon unravel.

One media business observer recalling Levin’s legacy described him as “thoughtful. A visionary. He saw media companies needed digital companies.” The response to that need, however, was misguided, and Levin would later concede that he stubbornly stuck to his guns and didn’t “sunshine” the idea to solicit colleagues’ feedback, to use the term favored by Netflix co-founder Reed Hastings.

The meltdown of AOL Time Warner obscured Levin’s earlier triumphs like leading HBO as its first CEO, helping negotiate Time Inc’s merger with Warner Communications and then shepherding the $7.5 billion Turner Broadcasting System acquisition.

When it first went on the air in 1972 (with Levin himself welcoming viewers on screen), HBO blazed a trail for the very concept of pay-television. The network delivered programming for a fee to consumers who had been trained for decades to expect the medium of TV to be available for free. After cable pioneer Charles Dolan hit on the initial idea as a solution to his New York company’s issues with delivering clear TV signals through the concrete canyons of Manhattan, Levin refined it. One early masterstroke was securing satellite distribution, giving HBO a head start on fellow cable upstarts like ESPN and Turner’s SuperStation.

After leaving the company he had built, run and then irrevocably hobbled, Levin turned away from media and toward spiritual pursuits. Teaming with Laurie Ann Levin, the onetime CAA agent and film producer who became his third wife, the exec founded Moonview Sanctuary in Santa Monica, CA. Billed as a “holistic healing institute,” it deployed a wide range of therapies, from acupuncture to “brain painting” to drum circles, to treat clients. In interviews upon its opening in the mid-2000s, Levin was candid about his need to seek out a higher purpose. Along with needing a dramatic shift from the rigors of a relentlessly paced life in the C-suite, Levin had recently been diagnosed with Parkinson’s and was continuing to process the trauma of his son’s 1997 murder.

Moonview is “a temple of transformation,” Levin proclaimed to New York magazine in a 2007 profile, “and I’m the poster boy.”

He recalled a realization he had upon waking up one morning. “I got up and said, ‘I’m 63, I have no belief system.’ As a CEO, I may have worked on mergers and satellites, but I never stopped and went inside and said, ‘Why am I here? Where am I going? What’s eventually going to happen?’”