Dogging a High-Flying Bird

Planes crash, coke spills, but Mr. O'Connor remains a mystery

After a Gulfstream II jet carrying four tons of cocaine went down in Mexico, suspicion fell on Fort Lauderdale aviator Clyde O'Connor, who had bought the $2 million aircraft just two weeks before.

But the 42-year-old O'Connor, who has been a fixture at the Fort Lauderdale Executive Airport for several years, isn't offering any answers as to how his red-white-and-blue plane wound up carrying so much Colombian coke.

Smile: Mysterious coke kingpin Joaquin "El Chapo" Guzman
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Smile: Mysterious coke kingpin Joaquin "El Chapo" Guzman

O'Connor is a man who drives too fast, disobeys the rules, falls into debt despite access to millions of dollars, and has been linked to no fewer than three plane crashes. He's never been an easy man to pin down, but he's been a veritable ghost since the September 24 crash, which is under investigation by authorities in Mexico, Colombia, and the United States.

So when the sandy-haired, six-foot-two O'Connor popped up in the lobby of an aviation business at Fort Lauderdale Executive just a week after the crash, it was the talk of the flying set.

"He was standing in the lobby of Banyan Air Service — and we all thought he was in jail in Mexico," said Joan Kuntz, a manager at Sheltair Aviation, O'Connor's former landlord. "It's always something different around here. Like we say at the airport, As the Prop Turns."

O'Connor wasn't the pilot on the flight two weeks ago (records indicate he no longer has a valid pilot's license), and he may be an innocent party in this affair — but the story certainly makes for choice soap-opera fodder. After all, it involves a chase by military helicopters, suspected CIA transport of terror suspects, and a tie to an elusive Mexican drug lord known as "El Chapo," or Shorty.

Authorities determined that Joaquin "El Chapo" Guzman owned the cocaine found in 132 bags among the Gulfstream's wreckage. Guzman is head of the Sinaloa drug cartel and considered the most powerful cocaine kingpin in Mexico.

Talk about a ghost; Guzman may be the most mysterious man on the planet. Known for using elaborate tunnels to transport cocaine into the southwest United States, he is rumored to pay millions to associates who harbor him in their homes and is said to change cell phones after each conversation. Currently, the Drug Enforcement Administration is offering a $5 million reward for information leading to his prosecution.

So how did O'Connor's plane come to carry El Chapo's coke?

Nobody seems eager to answer that question at the moment. DEA Agent Jeannette Moran is supposed to be the agency's media contact in Miami; she didn't return several phone calls for comment. O'Connor steadfastly avoided me.

I did find Gregory D. Smith, who reportedly co-owned the Gulfstream with O'Connor. Smith runs a company in Pembroke Pines called Global Jet Solutions. I called and asked him about the plane crash. "I'm not allowed to discuss that — I'm sorry," he said before hanging up.

Who told Smith to keep quiet, I wondered: O'Connor? The feds?

I called Smith again the next day.

"I'm not going to divulge anything," he said.

Still, some facts have come to light, thanks to reporting done mostly by the McClatchy News Service. (The Sun-Sentinel has failed to so much as mention the crash, and the McClatchy-owned Miami Herald has given it only brief attention.) O'Connor and Smith reportedly bought the Gulfstream from a pair of Brazilian businessmen on September 16. That same day, according to logs available on www.flightaware.com, the plane was flown from Clearwater to Fort Lauderdale Executive, which is operated by the city that bears its name.

Two days later, at 7:22 p.m. September 18, according to the logs, the 80-foot-long jet with tail number N987SA took off from Fort Lauderdale for Cancun. It's not clear precisely who piloted that flight. O'Connor has never been certified to fly a jet like the Gulfstream.

The plane picked up the cocaine in Colombia and was en route to El Chapo's gang when it ran into trouble over the town of Tixkokob, on the Yucatan Peninsula, Mexican authorities said. The Gulfstream apparently flew over Tixkobob for two hours before the Mexican military was notified and sent helicopters to chase it. That led to the crash in the countryside. There were no reported injuries. The pilot was arrested, as were two other men who allegedly tried to bribe officials at the crash scene.

The jet had its own mysteries. Between 2003 and 2005, it was flown from Guantanamo, the U.S. base in Cuba, to Washington, D.C., and Oxford, Connecticut, leading to speculation that the CIA might have used it for the "rendition" of terrorism suspects.

O'Connor is just as big a cipher. I first heard of him when I got a call from New York Post reporter Dan Mangan, who was looking for the Gulfstream's owners. Mangan pointed out that O'Connor apparently had written a strange letter to New Times about one of my stories.

Sure enough, a Clyde O'Connor wrote a letter to the editor from Tamarac, where he owned a condo. Published November 3, 2005, it was a response to a column I'd written about the accidental death of Fort Lauderdale police officer Jose Diaz:

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