Inside the Dirty World of an Outlaw Pilot

They'll run food or medicine, guns or drugs, for the highest bidder. They'll fly in planes that are held together by spit and duct tape. These ex-Soviet pilots are living lives that would frighten even James Bond.

By Matt Potter from Outlaws Inc.
Also in Reader's Digest Magazine February 2014

pirates of the sky

Mike King/Alamy

John is an England-based middleman who matches crews with aid organizations. He recounts one wildcat Il-76 job that left the American military command in Afghanistan breathless with awe. “The U.S. military had this huge generator they needed to get to an airfield site they were planning in the south,” he explains. “This was a remote area, and aside from a few pockets of U.S. troops, it was completely under bandit control. There was no fuel available for miles around, and none of the outfits we approached would touch it. They kept saying, ‘We’ll never get out again; how can we take off from an unprepared airfield with no fuel?’

“The job was priced between $60,000 and $70,000, but one day there’s a phone call from these Russian guys. They said, ‘We’ll do it, but it’ll cost you $2 million, in advance.’ The Americans didn’t have a choice at this stage, so they paid. And sure enough, right on time, this ex-Soviet air force crew flew in, in this battered old Il-76, unloaded the generator, and then sat down for a leisurely smoke.

“Just as the Americans were wondering how they were going to fly out again, up clatters this old minibus driven by some Afghan bloke—and these airmen just get in and drive off.

“The Yanks were going, ‘Hey, how will you get the plane back?’ And the crew said, ‘We won’t. We bought it for this job, and we’re ditching it here.’ Half a million dollars it cost them. They held it together with string, just long enough to land, cleared $1.5 million in profit, and left it to rust. It’s still there.”

The Four Turkeys Bar may be the sleaziest pilot pit in the whole of Entebbe, Uganda. Mickey, who arrived here in Uganda en route from the Congo to the United Arab Emirates, is so face-meltingly stoned that he can barely stand up. I am here with five very loaded mercenaries, and all their languages have mystically melded with mine into a series of half-finished gibberish, canny smiles of recognition, and shouted exhortations to drink. Scanning the dark, narrow room, I spot Ugandan hookers, tattooed South African military contractors, and enough Russian airmen to form a squadron. Referred to by names like Little Minsk and Russiaville, bars such as the Four Turkeys provide homes away from home for Russian expats, even showing Russian sports on TV.

Close by is the office of Iain Clark, the director of a respected global air charter. Clark explains how one flight in 2010 underlines the anytime, anywhere capabilities of outfits like Mickey’s. He’d hired one outfit to make a cash-ransom drop to some Somali pirates. The Russian-speaking crew weren’t allowed to know their destination. They were simply given a set of GPS coordinates and handed a cheap mobile phone. “They had to fly to certain coordinates given by the pirate ship,” says Clark. “Once they got there, the pirates would text them new coordinates.” The pilot and his crew shrugged. No problem.

The plane steered a steady course toward the GPS coordinates, rising eastward, passing over Kenya and the wild borderlands of Ethiopia, then out over Somalia and low over the pirate-patrolled sea. As they roared on to their destination, the phone in the navigator’s hand buzzed. There was a new set of coordinates. The pilot turned his plane in a wide arc and followed this new instruction. Keeping low, the crew scanned the water for boats, flares, RPG fire, anything. At this point, they could only trust it was not a trap. Then, at their next set of coordinates, they made visual contact with two small, fast boats in the water below.

The navigator’s phone rang, and an English-speaking voice said simply, “Don’t stop. Just drop the money.” The strongbox and its attached parachute were already positioned; the loading ramp, open. A crew member cut the lines, and $20 million was released into the sky. The last thing the pilot saw as he turned the plane for home was the pirate boats speeding toward the strongbox.

Because the whole operation was carried out on a need-to-know basis, nobody—not even Clark—really knew what was going on. But the aircraft’s operator, a Johannesburg-based Russian aviator, tells me the ransom was dropped on behalf of none other than Lloyd’s of London.

It’s an intriguing counterpoint and one that highlights the way big Western shipping businesses and former Soviet pilots, legitimate blue-chip multinationals and Somali pirates, coexist—if not happily then at least in a way that keeps the wheels of everybody’s businesses oiled and rolling. It’s also a fascinating snapshot of the weird force field of mutually repellent opposites that keep outfits like Mickey’s flying in the middle. When transactions are regularly called for between perhaps the world’s most venerable finance institution and AK-47–toting cutthroats in speedboats off the Somali coast, there’s only one mutually acceptable, ready, willing, and able group of middlemen. And it sure isn’t UPS.

Mike King/Alamy

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