How on earth did this pilot survive?

Flying drug barons, hairy landings in South America… by his own admission, Greg Madonna is lucky to be alive. This is one aviator’s incredible story

It’s the early 1980s, you’re in control of a Learjet that’s about to run out of fuel, and you’re pretty certain that the guy in the back is a Colombian drug baron.  
As aviation situations go, it’s not ideal.  
Yet it’s exactly the kind of thing that used to happen to Greg Madonna.  
Madonna’s story, documented in his book The Learjet Diaries, is a complex one. It variously features ambition, danger, corruption and death, with lavish expenditure clashing with unimaginable poverty. From an early interest in aviation to sweeping hangar floors at Pompano Beach Airport in north Miami after university, Madonna soon landed a job flying private jets, taking anyone who had the money wherever they wanted to go. Frequently, that meant either the Caribbean or South America.  

learjet 24
Madonna flew early Learjet examples such as the 24 and 36. Wikimedia Commons/Aeroprints

Now, it is a reasonable bet that anyone flying on a private jet from Miami to a city like Medellin in the early 1980s was not going to visit their grandmother. Until then, Miami had been a relatively sleepy city, but its under-the-radar profile – coupled with its proximity to Central and South America – made it the perfect American base for Colombia’s emerging drug cartels. With cities like New York grabbing the headlines for the country’s spiralling drug epidemic, the cartels were free to fly between Miami and the likes of Medellin as their business exploded. All they needed was access to private jets, and people to fly them.  

“You’d get a call to fly someone down to Colombia,” says Greg, chatting to Key.Aero over Zoom from Miami. “You’d be waiting on the tarmac at Fort Lauderdale and some 30-year-old guy in a Ferrari would pull up… you had a pretty good idea what he was doing for a living. We never saw anything but it was pretty clear what was going on. At the same time we would fly government officials from those South American countries on trips that were being paid for by the guys who we thought were in the drugs business.” 
As the pilot, though, Greg’s role was simple: do what you’re told, don’t ask questions. And, as it turned out, ferrying those in the drugs trade was only a fraction of the diverse clientele he would fly – everyone from celebrities to politicians would step into his Learjet, often unaware of just how dangerous it was.  
The danger was two-fold. This was a period seemingly bereft of any health and safety, or actually any safety at all. Greg’s first day involved a brisk guided tour around the Learjet 24’s controls; later that day he flew it for the first time. Weather information at the airports they were flying to was often non-existent, and the shoestring nature of the operation behind the private jet façade meant that the planes were usually under-fuelled and running on fumes by the time the destination’s runway came into view.  
Speaking of runways, Central and South America just happened to be home to some of the world’s most dangerous airports. Guatemala City, Medellin and Toncantin Airport in Tegioculpa, Honduras, are all etched in Greg’s memory for their hair-raising settings. “There was also La Paz in Bolivia, which had an incredibly short runway and a 500ft drop at the end of it – many pilots overshot it,” says Greg. He also reserved a special mention for the airport at St Thomas in the Virgin Islands. 
“The runway had a hill at the end of it, which meant you had to turn right immediately after take-off,” he recalls. “But landing at night was a challenge because there were no lights. It was very easy to misjudge it and come up short.” Crashed planes near Central and South American runways were a common site and, with most governments too cash-strapped to have them removed, they remained a permanent reminder to pilots like Greg of what might happen should their concentration levels drop when coming in to land.  
When Greg had first flown to Mexico, he was exposed to a word he would come to know well: ‘mordida’. “It literally means ‘the little bite’, where you give people money to get things done, and when I first saw it in action as a co-pilot I turned to the pilot and said, ‘Isn’t that bribery?’” laughs Greg. “But in order to keep the plane moving, everyone got their ‘little bite’. It was just how things were done.” 
For a middle-class boy from Florida, the clash of cultures between North and South America was starting to become clear. It would soon become graphically evident. “Things quickly got a lot more ugly,” says Greg quietly. “In order to protect their interests, businessmen would speak freely about assassinating people just to serve their dealings. That was very unappealing.” Yet, having been drawn into a world that turned out very different to the one he’d imagined, Greg soon found himself questioning his own behaviour. “I started doing a lot of things that I didn’t want to do,” he admits. “It was just what you had to do to survive.” 
Greg’s story of being an innocent young man flying Learjets, to becoming a cynical corrupt operator himself before finding redemption, is almost Great Expectations with planes; it’s a journey back to a recent era when aviation was vastly different.  
“I’m lucky to be alive,” he says. You can tell that he means it.

Tomorrow, we’ll be posting a longer video with Greg where he remembers some of his riskiest flights. To find out more about The Learjet Diaries, including how to buy it, go to