When every exit closes, you build a new one.
The bridge was out of the question.
Thousands of people were crossing daily. Venezuelan military on one side, Colombian armed forces on the other. And cutting through the jungle on both banks were the trochas—informal trails with no signage, no authority, and entirely controlled by ELN and FARC remnants. They were infamous for kidnapping. Infamous for smuggling—not just drugs, but medicine, food, and anything else Venezuela no longer had.
Which, by 2017, was most things.
I had a principal to get out. He was a sixty-eight-year-old CEO who had never done anything like this in his life. I needed to know if an extraction here was possible.
So, I went to look.
The Recce
My local driver dropped me five kilometers from the bridge. I got out of the car with a visible roll of toilet paper in my hand—the universal signal for a man who needs privacy in the tree line. Nobody looks twice.
Once out of sight, I stopped. Stood perfectly still. I opened my mouth slightly—a technique for stripping out the distraction of your own heartbeat so you can actually hear what's around you. I waited ten minutes. No suspicious movement. Then, I moved to the riverbank and sat in the jungle for thirty minutes. Watching. Smelling. Listening.
Then I stripped to my underwear, packed everything into my rucksack, kept my boots on, and crossed.
You don't cross a river in your clothes if you need to blend into a road six kilometers inside Colombia without being soaking wet and covered in mud. And you keeps your boots on—to protect your feet, and not with what's waiting on the other side.
The current was manageable. The other side was not.
There were no civilians. No traffic. Just the tree line and whoever was running that specific stretch that week. I went in far enough to confirm what I needed to confirm, turned around, and crossed back.
It was doable. But not for a sixty-eight-year-old principal. Threading a CEO through a guerrilla-controlled river crossing, wet, on foot, into ELN territory—that isn't an extraction plan. That’s a hostage situation you create yourself.
Cúcuta became Plan C.
The Drop Cache
Before it became Plan C, it was Plan B—and it was a real option.
The concept was simple: before the operation, travel to the border and bury a cache in the jungle. A weapon. A medical kit. A satphone. Money. Spare clothes. Log the grid on your GPS. On extraction day, cross alone; have a local driver take you to the principal's location, collect him and whatever company intelligence he's carrying; cross back together; dig up the cache; and move.
Clean in theory. The variables killed it.
You had the ELN and FARC on the Colombian side. You had a river crossing that was already a serious proposition solo. And you had a sixty-eight-year-old man who had never done E&E (Escape and Evasion) in his life, whom I would now need to walk through a guerrilla-controlled jungle crossing in the rain.
Some variables you can train around. Some you manage with planning. And some you just accept as disqualifying.
I added a strip of 5mg diazepam to my kit list anyway. A three-day road extraction with a panicking principal is a severe security risk. That’s not a medical decision; it’s a tactical one.
Two Days in a Hotel Room
I went back to the hotel, ordered whatever room service was available, locked the door, and spent two days on map study.
No dramatics. Just paper, grids, and the question of where else you can go when every obvious route is compromised.
The answer lay south. Santa Elena de Uairén. The Brazilian border.
Plan B: Brazil
The drive to Santa Elena is not comfortable. It’s parts concrete, parts dirt road that puts a permanent ache in your lower back. The area has significant illegal gold mining activity—criminal groups that are armed and highly territorial.
But they are manageable because they are transactional. If you hit a checkpoint, you don't get involved. You have a clean story, let them search the vehicle, and give the man in charge some money and a chocolate bar.
In Venezuela in 2017, chocolate was a luxury item. Handing one to a checkpoint commander wasn't a small gesture; it signaled that you understood the environment. That single act changes the dynamic from confrontation to transaction.
The border crossing itself was workable, and better organized on the Brazilian side. If Venezuela closed its borders—which was the exact scenario I was planning for—the sequence would be predictable: airports first, then official border crossings, then ports, then internal checkpoints and roadblocks. You plan for that sequence so you don't get surprised by it.
Which is why I presented the board with one specific requirement: a minimum of thirty thousand US dollars in small bills, held in the principal's safe. Not for emergencies—for checkpoints. It was a line item in the plan, not a contingency.
Plan for the worst. Hope for the best.
Plan A: The Coast
Bonaire, or any of the islands within reach by boat. Fast, low-profile, and clean—as long as patrol boat activity didn't make the coastal route impossible.
Which is why you don't build a plan around a single exit. You build a decision tree, and you test every branch in person before you need to use it.
- Plan A: Coast to Bonaire.
- Plan B: Road south to the Brazilian border.
- Plan C: Cúcuta river crossing, cache, and E&E.
The Outcome
I presented the plan to the board.
Two months later, they flew him out commercially while the airports were still open.
Which is exactly the right outcome. The best extraction is the one that never executes—because someone made the decision early enough that you still had clean options.
The plan sat in a drawer. The principal got home safely. And somewhere on the bank of a river outside Cúcuta, there is a patch of jungle that taught me everything I needed to know about what Plan C actually looked like on the ground.
You go yourself. In the rain. In your underwear. And you see what's actually there.