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."