Tom Freston, Runaway Mogul
Credit: Photograph by Mark Seliger
The day after we meet General Butt Naked, Tom Freston and I drive through a monsoon to one of the world's worst slums, called West Point, located along the northern edge of the Liberian capital, Monrovia. It is a maze of ghastly brothels and drug dens crammed cheek-to-jowl with adhoc dwellings of scrap tin and wood along a beach that seconds as a public toilet.

"Nothing like squeezing a slum in before breakfast," says Freston cheerfully as a local NGO worker named Macintosh walks us through narrow alleys flowing with sewage. Grave-looking villagers under makeshift awnings eye us suspiciously from cavernous doorways as naked children peek out with curious smiles. Freston, in this dank milieu, sticks out like an exclamation point in a white linen shirt and knee-high rubber boots, a giant rainbow-colored golf umbrella hoisted over his head. "This is the bottom of the barrel, man," he observes.

A few years ago, you would not have found Tom Freston here in Monrovia. He was too busy at the very top of the barrel, green-lighting multimillion-dollar movie deals and pacifying stars like Ozzy Osbourne and Tom Cruise, his virtual employees at Viacom. With his wife, Kathy, a trophy-blonde self-help author 20 years his junior, he was ubiquitous on red carpets and in Hamptons social pages, his weekends spent on David Geffen's yacht or smoking weed with Bill Maher in Beverly Hills.

But everything changed in 2006 when, following an afternoon playing tennis with Yahoo! CEO Terry Semel in Los Angeles, Freston came home to phone messages from his cantankerous boss, the then 83-year-old Viacom chairman Sumner Redstone. "Where the hell are you?" Redstone snarled. "It's easier to get ahold of President Bush than it is you...Call me, call me, call me."

Freston drove to Redstone's manse on nearby Mulholland, sat down in his living room full of exotic fish, and was summarily fired. Chief among Freston's failings, in Redstone's estimation, was missing the chance to buy social-media website MySpace before Rupert Murdoch's News Corp. snatched it up for $580 million. (MySpace, of course, would go on to lose many millions and get sold for roughly $35 million to a group of investors, including Justin Timberlake.) But poetic justice would come only later. Despite his usually unflappable disposition, Freston was stunned. "I've never been fired in my life," he tells me. "From anything. I've never failed at anything I've tried."

There would, of course, be a massive exit package to soften the blow – $85 million in stock options and other compensation. As the provocateurs at Vice Media put it in a recent video roast they assembled for him, Freston was "out on the streets with nothing more than a boatload of money, three huge mansions, a sweet record collection, and nothing else."

Freston could laugh at that. He was, after all, the man who ran the company responsible for 'South Park,' a foundational text of modern American irony. But he was also a man who'd been inside the same institution for two decades. "I'd been there for 25 years, a quarter of a century, my whole life's work. It had been the greatest run and ride," he says.

When it came to a dead stop at age 60, Freston admits that he was left with a curious emptiness. "I always imagined myself somehow as an electron around some atom, and you're just, like, bouncing around and spinning," he says. "There was a never-ending supply of places to go, people to see, things to do, and fitting it all in became kind of an art. So I never really got grounded. I never really spent a lot of time – you know, like, zero – being introspective at all."

Incidentally, the clue to Freston's future was waiting for him when he walked out of Sumner Redstone's house that fateful day: In the driveway was the car he'd owned for 30 years, a 1975 BMW 2002 he purchased new for $5,800 when he was a long-haired clothing exporter in Afghanistan. "The longest relationship of my life is with this car," he says. In 1972, Freston had ditched a straight job in advertising for the open roads of Europe, North Africa, the Middle East, and India. Without a plan, he learned how to find opportunity in the serendipity of travel. "It was the most transforming year of my life," he says.

And, it so happens, it was a blueprint for a reinvention.