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He Was in the Room for Trump’s Venezuela Pitch. Now This American Oilman Says He’s Ready to Start Drilling.

Venezuela used to be the crown jewel of South American oil. But for years, it’s been stuck in a mess of economic and political chaos. Lately, though, things are shifting. With oil prices steady and the Biden administration easing some sanctions, American oilmen are quietly reopening old Venezuela files and thinking about what’s next.

I’ve seen this story play out before—bold promises, sky-high hopes, and the lure of massive reserves. But this time, the angle feels a little different.

One American oilman, who was actually in the room when Donald Trump pitched the idea of “opening up Venezuela,” says he’s ready to get to work. And he’s not alone. The buzz is that Venezuela’s Orinoco Belt holds more proven crude oil than even Saudi Arabia. The global demand for oil hasn’t disappeared, that’s for sure. But turning those huge reserves into actual barrels flowing to market? That’s a whole other challenge.

The Opportunity—and the Risk

Let’s be real: Venezuelan oil isn’t your everyday crude. It’s heavy and needs special refining. The infrastructure? Well, it’s seen better days. And the political risks? They’re huge. But for those willing to roll with the punches and navigate a tricky landscape, the upside can be enormous.

Oil teams often get caught off guard—not just by the red tape, but by unreliable partners and sudden shifts in government policy. I’ve watched execs salivate over the size of the prize only to stumble spectacularly. Still, money talks. With some sanctions now loosened, there’s a mad scramble to be first in line, hoping to lock in deals before the window slams shut.

Why Now?

The energy world is in flux. OPEC+ is flexing, U.S. shale’s growth is slowing, and Russia’s war in Ukraine has seriously messed with supply chains. Every barrel counts more than ever. For American oil companies, getting back into Venezuela isn’t just about chasing profits—it’s also about having a strategic edge. Re-engaging with Caracas could help diversify supply sources and ease the impact of geopolitical tensions elsewhere.

That said, there’s déjà vu here. Investment banks are recycling risk reports from 2014, tweaking some numbers, and pitching them to boards hungry for growth. But the reality on the ground hasn’t changed much—rule of law is shaky, contracts aren’t always reliable, and the threat of expropriation looms large.

How Would It Work?

Most American oilmen won’t be going solo. The plan usually involves joint ventures with PDVSA, Venezuela’s state oil company. That means sharing profits—and headaches. You need local partners and have to be ready for sudden policy reversals. One day you’re a collaborator; the next, you’re the enemy.

The process kicks off with high-level meetings—often in hotel suites in Houston, Miami, or Madrid—followed by months of due diligence. Legal teams sift through old contracts while finance folks crunch numbers for scenarios at $60, $80, and $100 per barrel. Everyone tries to guess when the next crisis will hit.

And then there’s the day-to-day grind: getting equipment into the country, paying workers in a hyperinflation-hit economy, moving money in and out despite partial sanctions. Logistics can be a nightmare. It’s not unusual to see spare parts arrive on private jets or security teams hired just to safely reach the oil fields.

The Real-World Impact

Let’s be honest—a renewed American oil presence isn’t going to fix Venezuela overnight. The government needs hard currency badly, but oil money tends to stay at the top. Sure, some jobs might come back, but the deep scars from hyperinflation and poverty won’t vanish quickly.

That said, oil operations do create ripple effects. Drillers need caterers, truck drivers, welders, engineers—you name it. When oil flows, small towns can boom, at least temporarily. But political whiplash is always a risk. If Washington or Caracas change course, everything can grind to a halt in a heartbeat.

Investors Are Watching

Where there’s opportunity, money will follow. Hedge funds are already trying to get ahead of the curve. Private equity firms are quietly snapping up distressed claims, betting on a future boom. Some are even rolling the dice on PDVSA bonds, hoping for big payoffs if stability returns.

But there’s a catch. Doing business in Venezuela carries real reputational risk. Shareholders, activists, and board members often push back hard. One misstep can blow up on social media or cable news, not to mention the headache of compliance.

Limitations and Caveats

This isn’t a sure bet.

Sanctions relief is partial and could be reversed in a flash. A new administration in Washington could slam the door shut overnight, leaving billions stranded. I’ve seen teams get burned—contracts canceled, equipment seized, employees unpaid.

Plus, you need a tolerance for chaos few firms possess. Even with top-notch lawyers and political risk insurance, there’s exposure to currency swings, civil unrest, and shaky legal systems. Many teams find it overwhelming and pull out before even drilling.

And don’t forget the bigger picture: the push toward renewables and ESG investing. Some investors simply refuse to fund new oil projects, no matter how tempting the returns.

A Calculated Gamble

At the end of the day, American oilmen ready to drill in Venezuela are making a calculated gamble. They’re betting the rewards will outweigh the risks—and that the window to act stays open long enough to cash in. The odds are tough to call. But as energy security climbs the political agenda and easy oil sources dwindle, it’s easy to see why so many are tempted to take the plunge.

Will this wave of investment stick or fizzle like so many before? Time will tell. But for now, the buzz is real—and the drill bits are ready.

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