Tom Freston, Runaway Mogul

Mj 618_348_the runaway mogul
Photograph by Mark Seliger

On the western coast of Africa, in a rambling Liberian ghetto called Chocolate City, a former cannibal is sitting under the shade of a tin-roofed hut explaining how he sacrificed humans to placate a jungle god. “I didn’t see it as cruel at the time,” the squat, muscular man says in his thick patois, a bead of sweat inching down his grim face. “I saw it as a mediating role between the deity and the people.”

A congregation of about 20 teenage boys – an assortment of reformed killers and drug addicts – sits on plastic chairs and listens raptly as the man in a baseball cap and brown military shirt sleeves confesses to leading a militia of drug-fueled child soldiers to kill a purported 20,000 people during a horrific period of unrest in the 1980s and ’90s, and to eating children from his own tribe to gain spiritual favor in battle. Until he found Jesus in a burst of white light – shortly after hacking his last victim to death – he merely saw it as part of the job description. “Every time I do this sacrifice,” he says, “the battle immediately turns against the enemy. Or turns in favor of us. They would start running.”

He also believed nudity was his armor against enemy bullets –thus his wartime moniker, General Butt Naked.

The three white Americans sitting alongside Butt Naked are duly sobered by the testimony. And in the raw reality of the moment, there is the hanging question of why their leader, Tom Freston, the spike-haired media mogul who helped create MTV and once ran the film and TV company Viacom, has brought them here, to a bleak neighborhood in a failed and lawless state, to meet a murderer. Freston and his companions, part of a larger delegation of pampered Westerners in SUVs who arrived in Liberia about four hours ago, couldn’t look more conspicuous if they’d been dropped out of a time machine.

But shock, it turns out, is exactly what Freston came here for. Technically speaking, he is in Liberia as chairman of the ONE Campaign, the nonprofit co-founded by his friend Bono, which flew in the delegation of Washington politicos to witness the good works of the G8 countries in fighting AIDS and malaria. The group, according to the itinerary, will visit a hospital, a factory, and a farm, examples of successful development efforts sponsored by Western powers, and then fly east to Ghana to see a rural schoolhouse and help the Peace Corps install mosquito nets in a remote village.

The Butt Naked meeting is not on the agenda. Rather, it’s a freelance caper cooked up by Freston, the executive who introduced us to reality TV 20 years ago with ‘The Real World,’ to provide a bit of garish spectacle to an otherwise earnest mission. It is, in Hollywood-ese, a Tom Freston Production. Freston procured Butt Naked’s cellphone number from a friend and suggested it might be amusing if, while in Liberia, he introduced him to our other traveling companion – the right-wing Christian leader Ralph Reed.

The archconservative evangelical meets the born-again cannibal? “That would be like an Ali G move,” says Freston.

And so here we are, sitting with this monster-turned-minister and his Christian converts, homeless kids he found living on the streets (some sleeping in empty caskets in the local graveyard), who stare at us with expressions of almost preposterous hope in this postwar wasteland where electricity is scarce and plumbing is nearly nonexistent (as is, apparently, justice for war criminals). Ralph Reed had little idea what he was getting into when he agreed to the unscheduled outing, and his jaw is appropriately loosened in horror as Freston had planned. But Freston looks pretty shell-shocked himself. “That’s quite a story,” is all he can manage to say.

Equally shocking, however, is how the presence of Freston the big-time American media mogul, whose network of powerful friends includes Rupert Murdoch, Jeffrey Katzenberg, Bob Iger, and Tom Cruise, automatically turns this situation into a kind of business meeting. Reed says he knows a couple of evangelical churches that might like to meet the reformed man-eater. And the reformed man-eater, who is now known as Joshua Blahyi, is happy to oblige, handing Freston and Reed copies of his published memoir and the documentary about him that aired at the Sundance Film Festival in 2011. “Some people still think I should be hanged,” he notes.

Before he goes, Freston sidles up to Butt Naked for a photo op, a postcard he’ll email to Bono and other friends. We then climb into the SUVs, roll up the windows, and heave a collective sigh of relief. Freston says he was too stunned to ask the pressing follow-up question: “What does human flesh taste like?”

“I couldn’t believe my ears,” he says. “I felt like I’d been taken back to some prehistoric time.”

But all things considered, he declares the outing “a good little adventure,” as he settles into the SUV. He pulls out a bottle of antibacterial gel from his safari jacket, squirts a little into our palms, and laughs: “You’ve been shaking hands with General Butt Naked!”After more than 30 years in the entertainment business, Tom Freston knows how to make the talent feel at ease. Described by friends as a mash-up of Jack Kerouac and Jack Welch, who weds a Zelig-like talent for friendship to a pirate’s eye for opportunity, Freston saw his job at MTV Networks as making people like Jon Stewart or Bono or Beyoncé feel as if they were stars in a corporate firmament he was running on their behalf. In Freston’s world, where everything and everyone are potential content to be provided to somebody somewhere, Ralph Reed and Butt Naked might very well be the next ‘Beavis and Butt-Head.’

“He would never say, ‘Gee, that guy is a rich, right-wing Republican, therefore he’s my enemy,'” says Bill Flanagan, a longtime friend from MTV. “In the same way, he’ll go hang out with a cannibal.”

Indeed, even Butt Naked becomes an F.O.T. (Friend of Tom), asking Freston on the phone the next day to help him procure a visa to the U.S. so he can hang out with Reed and other American evangelicals. (Freston says he’ll try, though the murderous coup might be an issue.)

A child of the 1960s, Freston spent his late twenties and early thirties as a clothing exporter living in Afghanistan and India – until he lost his fortune and stumbled, serendipitously, into a job at a nascent cable channel in 1980. The rest is the history of MTV. Freston would run the network for 18 years, turning it into a global powerhouse by introducing reality TV and hip-hop to mainstream audiences, expanding MTV into Asia and Europe, and eventually overseeing the parent company, Viacom, one of the largest film and TV conglomerates on Earth (including ‘The Daily Show,’ Nick at Nite, Spike TV, and Paramount Pictures).

Seven years ago, however, Freston got fired from Viacom, extinguishing his media-mogul mojo and throwing him into a post-power-player identity crisis. As he told a crowd of college students in 2007: “Here I am giving a commencement speech when I’m back right where I started, wondering, like you, ‘Dear God – what the hell am I going to do now?'”

If Freston were a typical corporate chieftain, he might have sought a new corporate perch and tried recovering all the trappings of power: the easy access to celebrity and fame, the private jet, the company cars, the armies of assistants to micromanage his every waking minute – minutes he would spend determining who gets paid the millions and appears on TV and movie screens around the globe. But he didn’t do that. Instead, he has tried reinventing himself as something more idiosyncratic: an independently wealthy media broker with an assortment of off-grid interests that, together, seem to circle back to a previous incarnation of Tom Freston – the one who freewheeled his way to fun and profit in the 1970s and then lucked into the best job in American media.

In the past several years, he has become an adviser and investor in the insouciant male-centric media company Vice, which he likens to an early MTV, and a consultant and board member to Moby Group, a fast-growing TV company in Afghanistan that Freston also likens to an early MTV. Simultaneously, he’s helped re-engineer the antipoverty campaigns founded by Bono, a friend Freston helped make famous in the early days of MTV. His new schedule has made him a nonstop traveler to the Middle East and Africa, places he roamed in his twenties, and later as a CEO expanding the global reach of MTV.

At 67, Freston has the wealth and access to seed youthful new media ventures and concoct global adventures worthy of his own legend. What’s not yet clear is whether he can reinvent his own wheel.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.

Viacom, in a sense, had become for Freston what his own hometown had been back in the 1960s: a luxurious trap. He’d grown up in the Waspy enclave of Rowayton, Connecticut, a commuter suburb where five o’clock cocktails and Frank Sinatra were a way of life. His father, a PR executive at a paper company, had no interest in life outside the city limits. “My whole youth, we went on a one-day trip to Mystic Seaport,” says Freston. “It was the only trip we ever took, and it was up and back in one day. Some smelly fucking whaling ships.”

But Rowayton gave Freston a distinct taste for the good life. When he got a job as an umbrella boy at the Wee Burn Country Club at age 16, “I’d meet all these kids my age who didn’t have to work and dressed better and drove cars their parents had bought them. It seemed outstanding to me.”

His worldview was recalibrated in the summer of 1965 when, while working as a bartender at a leafy upstate resort at Lake George, in New York, he met a group of bohemian dropouts who read Jack Kerouac, smoked pot, and grooved to the going hit “Like a Rolling Stone.”

“They had a free life; they’d make money and meet all the girls,” he recalls. “It was a whole subculture for me, very alluring.”

Back at his sleepy college of St. Michael’s, in Vermont, Freston became the countercultural Johnny Appleseed to his more provincial friends, growing his hair long, subscribing to ‘Rolling Stone,’ and rolling the joints.

He was a natural entrepreneur, organizing for-profit keg parties featuring live bands. As manager of the school cafeteria, he assigned the dozen available jobs to himself and a couple of other friends, did all the work, and split the pay for 10 ghost employees. “He had operations and schemes going all the time,” says his brother, Bill Freston. “That was always the deal. Undermining the system. ‘Oh, they’re such good boys’ – meanwhile, a lot of drinking and smoking dope and partying. I don’t think that’s changed much.”

After graduation, Freston applied to business school at New York University, primarily to avoid Vietnam. But he was turned on again – this time to Peter Drucker, the business management consultant, who taught a course in innovation and change, two concepts that seemed radical in the buttoned-down world of business. “I knew I wasn’t a painter or a musician or anything, so if I wanted to be creative, I could gravitate toward that,” Freston explains. “Innovation is taking two things that already exist and putting them together in a new way. I started getting excited. Maybe there’s a place for a creative businessman.”

In 1969, diploma in hand, Freston rewarded himself with a cross-country ramble, including a layover in the Virgin Islands, where he tended bar and tried LSD for the first time. (“Let’s do that again,” he told his female companion the next day.) But he returned to New York and went straight, getting a job at an advertising firm, Benton & Bowles. He chafed at the square life. “I got increasingly disillusioned with it and talked to friends on the outside who were living a free life, and I’d say, ‘Man, I’m kind of trapped here.'”

So Freston left for Europe on a yearlong plane ticket, with no plans other than to see exotic sights and chase girls. “My parents were fucking appalled,” he says.

Invariably, Freston found opportunity. In Greece he met “this gorgeous hippie chick” on the beach who was selling Indian fabrics to German tourists and making a killing. “I kept thinking, ‘Maybe I could do this on a larger scale,'” says Freston.

He spent the next eight years building a clothing business from scratch, traveling around India and Afghanistan looking for fabrics and developing women’s fashion designs for Western department stores. The company was called Hindu Kush, named for the Afghan mountain range – but also a strain of Oriental cannabis with which Freston was not unfamiliar. He opened a factory in Delhi with a local merchant he befriended (and still knows) and established a headquarters in Afghanistan, where he could live like a hippie king in Kabul, complete with his own butler and servant. He threw lavish parties for NGO workers, beatnik drifters, and soldiers of fortune he met during his travels. By the late Seventies, Freston says, Hindu Kush was a “multimillion-dollar operation. We were selling in Australia and Holland and the U.K. and all through the United States. We were making a lot of money. I couldn’t believe it. It was a countercultural capitalist thing. Working like crazy. More than I would have in a regular job.”

Then came a violent coup in Kabul in April 1978, which forced Freston to flee to Peshawar until the fighting blew over. It didn’t, however. The new Communist regime, he says, began killing off local businessmen, so he shut down his Afghan operation, which was 30 percent of his business, and fled to India. “I hated to be shut out of a place I truly loved,” he says.

Within a few months, the Carter administration enacted a new trade policy that put a cap on Indian clothing imports, which froze Freston’s business midstream, leaving him with a big inventory and nobody to sell it to. As quickly as it had begun, Hindu Kush was kaput, leaving Freston $500,000 in debt.

“All of a sudden, I’m wiped out and it’s 1979,” he says. “I came back and said, ‘I’ve got to find another way of life.'”

We’re on a bus rambling up the Cape Coast of Ghana to Elmina, site of the world’s largest slave castle, which was run by the Dutch in the 17th and 18th centuries. The road is clogged with motorcycles, some with four people astride them, and brightly painted minibuses spitting black smoke. Street sellers flash their wares at our bus as lanky women with gigantic baskets of fruit on their heads saunter through the heat.

Tom Freston is sitting up front, headphones on, punching out emails to producer Brian Grazer about a script idea involving John Glenn and Charles Lindbergh.

We flew here from Liberia on a borrowed 767 with cream-colored chaise longues and private sleeping quarters. There was a lunch of grilled shrimp and cabernet. From the grimmest of slums in Liberia to opulence at 30,000 feet in the space of a few hours – it’s the kind of cultural and socioeconomic whiplash that Freston is used to. He isn’t one to go native. He carries Hollywood and Manhattan in his BlackBerry 24/7. Even in the wilds of Chocolate City, where chickens and stray dogs roam muddy roads and children play in abandoned buildings, Freston wears Prada sneakers and carries a Jack Spade bag.

If there’s anything that seems to acclimate Freston, it’s music. From the back of the bus, I text him: “How’s it going?” He texts back: “Into da music, mon. Very nice West African playlist…perfect soundtrack.”

Later, he tells me it’s his favorite compilation of Ghanaian highlife music, The ‘Guitar and the Gun,’ from 2003. “They had an unbelievable scene in the Seventies and Eighties,” he says. “A whole psychedelic era, garage bands, all kinds of shit.”

When Hindu Kush folded, Freston read his first self-help book, ‘What Color Is Your Parachute?‘ – the bible of aimless Baby Boomers – and concluded that music was his passion. Luckily for him, while he was in Afghanistan, his brother had become an executive at Columbia Records: “‘We’re going to see Bruce Springsteen at the Bottom Line,’ and I’d say, ‘Man, I could do this. This looks like fun,'” Freston says.

For Freston, snagging a job interview with the not-yet-named MTV was a stroke of unimaginable luck. “They said, ‘We’re looking for people who have no experience in television,'” recalls Freston. “I said, ‘I’m your guy. They didn’t even have television where I just spent the last eight years’… They all assumed I was a drug dealer.”

Freston was MTV’s fifth hire, soon to become a business partner to a whole generation of pop stars, from U2 to Fab 5 Freddy, whose careers he would help mint in the music-video era. Early on, he found himself at a ski resort in Gstaad, Switzerland, where David Bowie had agreed to shoot the famous “I Want My MTV” promo clip. “I’m in the sauna with Bowie,” Freston recalls, “and who else is there? Paul McCartney! Everyone had towels on.”

It took him about four years to pay down his debt. Seven years in, he was CEO. While he helped develop the channel, Freston imprinted the corporate culture with the free-range ethos he’d learned as a bootstrapping exporter. “He has that easy, affable nature that rock & rollers like to be around because they’re a little anxious around obvious corporate-type people,” says Bono. “This belies that he’s expert in a boardroom, and that is his secret weapon. Tom is highly organized and better briefed and more articulate than a lot of those corporate people. It’s just that he doesn’t look like he is.”

Judy McGrath, MTV’s former programming chief, and Freston’s top lieutenant, says Freston’s grooviness masked his relentless will to succeed. “We know executives who flame out because they get captivated by the glamour,” says McGrath. “It was never, ‘Let’s just party all the time.’ You would have a blast, but it wouldn’t feel like work. It’s like Tom Sawyer. You didn’t even realize you painted a fence.”

Freston became as rich as he’d ever dreamed back at the Wee Burn Country Club. He was married in 1980 to Margaret Badali, a Wall Street trader, and had two sons, but it was over by 1993, his relationship strained by his nonstop lifestyle. Freston says what he loved most about his job was the power to make people into stars, to “take somebody from out of the crowd and hold them forward and all of a sudden they’re some big phenomenon.”

The cultural contributions of Freston’s success ranged from the memorable and progressive (‘Beavis and Butt-Head,’ ‘Yo! MTV Raps,’ ‘SpongeBob Squarepants,’ ‘Blue’s Clues’) to the utterly stupid and vacuous (‘MTV Spring Break,’ ‘The Real World,’ and pretty much the entire reality-TV genre that came after). What you couldn’t argue with was its export value.

“His global background and instincts are superimportant,” says Craig Marks, co-author of ‘I Want My MTV: The Uncensored Story of the Music Video Revolution’. “He oversaw MTV’s worldwide expansion- Europe, Latin America, Asia. That’s where MTV made a ton of fucking money. He was the perfect guy to do that. He had that background; he had that field of vision.”

Under Freston, MTV Networks, which included Nickelodeon and Comedy Central, grew into the biggest TV network in the world. It’s why, in 2004, Redstone offered him a job as co-operating officer of Viacom, along with CBS president Les Moonves. It took Freston 24 hours to decide. And even as he accepted, he realized he was sacrificing the values that had made him successful to become a full-time servant to Wall Street. “For the first time in my career,” he says. “I was taking a job that I wasn’t dying for.”

In exchange for the power profile, Freston now lived on a treadmill of corporate panels put on by investment banks, always preparing for the next grilling by Wall Street analysts. Redstone hovered over him. “I’d come in in the morning, and there would be a stack of faxes from him,” says Freston. “‘What about the stock price?’ ‘We didn’t do this in the earnings call.'”

Freston felt he did everything right, but the stock market did not agree. When Viacom’s shares stagnated, Redstone decided to split the company and give Freston half the cable and film properties and Moonves the other half, CBS. But in the new digital revolution, where Google and Yahoo! were the dominant paradigm, an old-line content company like Viacom struggled. Eight months in, Freston was fired.

To escape the media glare, he took off on a trip to Burma. He says he was humiliated by reports of his golden parachute because he felt it exposed him. “The kids are coming home and saying, ‘Dad, everybody at school says you made $85 million,'” he says. “I pride myself on having relationships with people from all economic strata. You didn’t want to be seen as some rich white guy. It wasn’t in keeping with my delusional self-image.”

He was bombarded by messages from prospective employers upon his return, but he decided it was time to reexamine the color of his parachute. So he organized a trip to Africa to see the Festival in the Desert in Mali, the famously remote concert of Tuareg music frequented by musical adventurers like Robert Plant. For companionship, he took his MTV friend Bill Flanagan and his two favorite music moguls, margarita man Jimmy Buffett and Chris Blackwell, the founder of Island Records, who first signed Bob Marley and U2. (They dubbed themselves the Buktu Brothers.) In 2005, Blackwell had hosted Freston’s 60th-birthday bash at his GoldenEye resort in Jamaica, where Freston’s all-star friends, including Jann Wenner and Graydon Carter, swam, danced, and listened to reggae bands, and Rastafarian waiters walked around offering joints.

Buffett flew the gang in his private jet to Mali’s capital, Bamako, where on a lark they sought out the members of a defunct 1970s Afro-Cuban group they all loved called the Super Rail Band. Freston asked a local if any of the original members were still around, and a phone call later, the story goes, the guitar player appeared and said the band would reunite for $300. “Next thing you know, some amps show up and the Super Rail Band shows up,” marvels Buffett.

In Ghana, the ONE bus takes us to a village tucked in a wooded grove along the Cape Coast, where a couple hundred villagers come together to celebrate the opening of their first working bathroom, an adobe-style outhouse built by the U.S. government. A festival in the desert with the Buktu Brothers it’s not. The ONE delegation, about a dozen consultants from Washington, including Clinton-administration press secretary Dee Dee Myers and former Minnesota senator Norm Coleman, gathers to watch women and children in ceremonial costumes dance to pounding djembe drums. A large, corn-fed conservative from Kansas is made king for the day, outfitted in a batik robe and a golden crown – and then hoisted, precariously, by skinny villagers on a ceremonial plank.

“White man’s burden,” Freston quips.

Later, Freston walks up to the new outhouse and announces, “I want to inaugurate this thing!”

Maybe it’s just his serene moguldom, but Freston, whose craggy features recall Lee Marvin after a bong hit, is a little too cool for the earnest NGO crowd. Freston believes Africa is a place of vast potential, but on the ground, among actual Africans, he can seem a bit detached, distracted by the lure of his BlackBerry, not quite the lonely planeteer his friends whisper about at dinner parties. Greeted by a village elder in a robe and crown and carrying a golden scepter, Freston blithely snaps his photo before shaking his hand. He’s no Margaret Mead.

Freston, however, did manage to salvage Bono’s organization from dissolution, which is why we’re here at all. After his firing from Viacom, one of Freston’s first calls was from the Irish rock star, whose advice Freston sums up as “Fuck ’em.” “How much more successful can you get?” Bono remembers asking Freston at the time. “He was right at the top of the pyramid. He had some crazy billionaire standing on his neck, but here was a guy who had much life force and wisdom.”

So Bono conscripted Steve Jobs – Apple is a sponsor of Bono’s AIDS charity – to lobby Freston to overhaul his various nonprofits. After a visit to Bono’s mansion in the south of France, Freston agreed to travel to Washington for a crash course in foreign policy and nonprofits, meeting up with political heavies like former secretary of state Condoleezza Rice and Bush White House chief of staff Josh Bolten.

Bono says he admires Freston for his ironic sense of humor, a useful trait when faced with nonstop scenes of poverty and disease. He also liked that Freston could party pretty hard. “We can stay up later than anyone, and we can get up earlier,” says Bono. “That’s why we should be roommates.”

But joining Bono, in a way, was easy. The job involved not only cleaning up balance sheets, but also a heavy regimen of travel, including a trip to Dakar, where they were treated to a private performance by Senegalese superstar Baaba Maal. More complicated was Freston’s reentry into the media, as Oprah Winfrey courted him for advice when she began to formulate her cable-TV channel, OWN. Freston resisted her entreaty to become its CEO but signed on as a consultant and board member, saying he never really related to Oprah’s audience.

But Freston soon discovered a TV audience he could really relate to – 30 million war-ravaged Afghans who had just begun watching TV. Before leaving Viacom, he had met an ambitious media executive named Saad Mohseni, who told Freston how television was skyrocketing in his home country. Nearly 70 percent of the population was now watching TV, and Mohseni’s company, Moby, had captured most of the viewers.

In May 2007, Freston returned to Kabul for the first time since 1978. “I was like Rip Van Winkle,” he says, awaking to a country with bullet-pocked barricades, air pollution, and women in burkas – nothing like the hippie haven of his youth. The young TV startup, however, left him “dumbstruck.” “Everyone in their twenties, no one who really had ever worked in TV before – few knew what they were doing, but were learning fast and on the job,” he says. “It looked like an Afghan version of MTV, circa 1981.”

Freston believes television, even trashy content like game shows and soap operas, can democratize and acculturate places like Afghanistan more quickly and more effectively than politics – the way MTV urbanized a generation of teenagers in rural America some 25 years ago. It doesn’t matter to Freston if ‘Beavis and Butt-Head’ is the lingua franca of the masses: It’s still the great cultural unifier. Most Afghans, he says, “can’t really read, so TV is a great place to get various signals about various forms of socialization. I mean, it’s the most powerful thing that’s ever been invented. It’s nearly irresistible.”

He didn’t invest in the company but signed on to become a member of Moby’s board of directors and quickly brought his connections to the table. Over lunch in Manhattan, he introduced Mohseni to News Corp. chairman Rupert Murdoch, who was intrigued with the satellite-TV business Mohseni was gearing up in Iran, called Farsi1, which was dubbing syndicated content like South American soap operas and becoming hugely popular. Murdoch bought a 50 percent stake in the company – it’s now the number-one TV network in Iran.

It’s uncertain what will happen in a place like Afghanistan in the next few years. Will Moby, like Hindu Kush before it, be sunk by a violent coup, this time by the Taliban? Mohseni has convinced Freston that the Taliban won’t regain power. “I know this may seem optimistic, given all the news reports to the contrary, but they are not well liked in the country,” Freston tells me.

“There have been huge social changes in Afghanistan in the past 10 years and more connection to each other and the outside world,” he says. “Moby and the other TV networks and other media have played a huge role.”

Moby’s latest project is building a soccer league in Afghanistan. Freston sees it as a creative way to generate goodwill and mediate the country’s ethnic and tribal tensions through televised sports. Naturally, Freston had a front-row seat to the semi-final match between De Spinghar Bazar and Toofan Harirod.

“He’s not insular, he’s not inward-looking, he’s always looking out,” Mohseni continues. “He’s a great ambassador for his country. I joked once: He’s the sort of American who gives America a good name.”

As the stories of Freston’s new life have spread among his friends in Hollywood and Manhattan – did you hear about the time he almost got stampeded by elephants in South Africa? – he’s become a wise man to fellow media pooh-bahs, offering a glimpse of a post-power life to Bob Iger, CEO of Disney, and Jeff Bewkes, CEO of Time Warner, for whom a summary firing is always only a bad quarterly report away. “They talk to me now: ‘What’s it like on the outside? Is it really all right?’ You’re in the machine so long you can’t imagine it,” Freston tells me, as we motor by a rubber tree forest in Liberia. Most other media moguls, he says, “don’t necessarily have any curiosity, and, I think, they have somewhat of a shrunken view of human nature. And also, an outsize ego. I don’t really have an outsize ego.”

His friend Bill Flanagan goes further: “Tom Freston is a master at living life, and has lived a near perfect one. It may just be a mathematical probability that at least one guy had to do it right the whole way,” he says.

Back from Africa, we’re sitting in Freston’s Upper East Side townhouse in Manhattan, a home once owned by Andy Warhol. Inside, there are bookcases stuffed with travel books and gleaming tables cluttered with baubles from his adventures, a virtual museum of Freston’s long, strange trip. Here is the hookah he picked up in Beirut, and the statue of Chairman Mao with a pile of beaded necklaces draped around his neck. I recognize those beads: When we were on the Cape Coast in Ghana, a couple of Rastafarians sold us jewelry under a palm tree on the beach, and Freston roped them around his neck, one by one, while he haggled over the price. “When I get a new girlfriend,” he says, “I’ll have a big supply.”

This year, Freston and his wife, Kathy, announced their separation after 17 years of marriage – Freston’s second. When he left Viacom, it became clear that Kathy Freston had different priorities than Freston did. Her views on meat-eating – Kathy was a zealous vegan with a growing self-help empire – didn’t easily transfer to her husband. Aside from his love of steaks, Freston couldn’t seem to keep away from countries where veganism, and very often plumbing, is a luxury.

Consequently, at 67, Freston lives alone in three empty homes. The necklaces? “I didn’t know what to do with them,” he says, “so I thought they’d look good on Chairman Mao.”

With Freston, nothing is quite what it seems. He’s a groovy, devil-may-care lark-about – until he’s cutting Rupert Murdoch in on an Iranian satellite deal. Freston is beloved among his friends, a font of exotic tales and smart takes on the media biz. But his closest confidants, people who have known him for years, consider him a bit of a sphinx, uncertain of exactly what lies behind the deep-set eyes and easy-breezy grin. “Tom is an authentically cool person,” says Graydon Carter, the editor in chief of ‘Vanity Fair’. “And cool people are somewhat hard to penetrate.”

As it happens, Freston is still a mystery to himself, as well. He realized, during an African safari a few years ago, that his fast life had precluded much self-knowledge. “After we almost got killed by the wild elephants,” Bill Flanagan recalls, “we were hanging back, sun going down, and Tom said, ‘You know, if you just keep going and going and going, from place to place, from adventure to adventure, it’s fantastic; you never have to face yourself.’ Kathy and I looked at each other, and said, ‘Tom, I think you’ve just had a breakthrough.'”

On his wife’s advice, Freston started therapy, including some unusual sessions involving a powerful hallucinogen called ayahuasca, a drug derived from a South American vine that inspires visionary experiences. He began to explore a terrain most foreign: his own interior life. “I looked at it like it was some other country I had to go to,” he says.

He has a hard time verbalizing what, if anything, he derived from his vision quest. But ultimately, he concludes, his wild ride from Afghanistan to MTV to Viacom and back again was one long sprint from the confines of Rowayton. America, observes Freston, has always been a country in which the Puritans were at war with the libertines. Rowayton, he says, was the Puritan stronghold “from which I’ve been eternally trying to escape. That’s been sort of the journey.”

And yet he has never fully escaped, a fact that is hard to avoid now that he’s alone. When I ask about his recent separation, Freston’s eyes well with tears. He calls it “a big hole” in his life – a hole, he says, he can only think to fill with…more travel, more music. “There’s almost nothing that distracts you from your day-to-day problems more than a trip,” he says, brightening. “You’re totally consumed in the present, you’ve got new sense impressions, you’ve got all this stuff to digest….It’s probably healthier for you than drinking.”

And so Tom Freston chases the sunset to elude the sunrise. What was it the bard said in the summer of 1965? Like a rolling stone. But Tom Freston’s friends – the whole charmed BlackBerry of them, from the movers of Hollywood to the street vendor in Kabul – don’t require the inner life of Tom Freston to enjoy the company of Tom Freston. They just want to see what happens next.

“I’m not looking to solve the mystery,” says Jimmy Buffett of his old friend. “I’m sure there’s something there I don’t know. But one day maybe I’ll figure it out.”

For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!