Category: Southern Caribbean

US & Venezuela On The Brink

December 14, 2025 / Ben Stubenberg / 2 Comments

What could possibly go wrong in the Southern Caribbean?

The day of reckoning for Venezuela and the United States fast approaching! $40 billion in military assets and 15,000 sailors and Marines deployed to the Southern Caribbean appears not to have persuaded Venezuelan president/dictator Nicolás Maduro to step down. Nor has the blowing up of skiffs purportedly carrying narcotics somewhere (though not to the US). Nor have sanctions or the seizure of an oil tanker loaded with Venezuelan crude. Threats of airstrikes and even putting US troops “on land” have done nothing either to move the needle on regime change.

So how will this madness play out? The parallels to the run-up to the Iraq War reverberate almost a quarter century later. Here’s my take as a former DoD threat analyst.

Start with the premise that Trump has invested too much in this vanity adventure to just order the fleet to return home with nothing to show. In a still hazy foreign policy, Maduro would be forced out and somehow Venezuela’s democratic leaders would emerge from hiding and take the mantle of power while riding on a wave of simmering anti-Maduro sentiment.

American actions did appear to embolden the underground pro-democracy elements. They see a US pressure or even a direct intervention as their only chance to regain power in Venezuela. Last week Nobel Peace Prize winner Maria Corina Machado took a dangerous risk (along with others) to escape the country by boat to the island of Curaçao to the north. From there she traveled to Oslo to meet with the Nobel Peace Prize Committee that granted her the prize (accepted earlier by her daughter). Her Nobel Peace Prize and now freedom outside of Venezuela gives her a much larger platform to advocate for regime change and restoration of democracy with American help.

But there is no pro-democracy guerrilla movement in mountains to oppose the Venezuelan military. In fact, there is no organized group of freedom fighters with firepower that US could theoretically support clandestinely or openly. And despite all the bluster of troops “on land,” a couple of thousand Marines on the aircraft carrier Gerald R. Ford won’t be able to topple an entrenched Maduro with heavy support from his generals and admirals. In fact, even a coup is unlikely from these top military leaders.

It is worth examining why the generals and admirals are so loyal to Maduro. There are at least 2000 generals and admirals in the Venezuelan army. Probably more. That top-heavy number comes to a ratio of about 1 general/flag officer to 75 soldiers or sailors in a military force of 150,000.

By comparison, the US has about 1 general/flag officer to 1400 soldiers or sailors commanding a force of 1.3 million. (And even that is a bit top-heavy due to “rank-creep.”) Why the disproportionate ratio in Venezuela? Because Maduro has cleverly promoted these men to prestigious and powerful command positions to ensure more loyalty. Most of them are directly involved in and profiting off of major businesses in Venezuela. In other words, serious corruption and therefore a strong motivation to maintain the status quo. Oppose Maduro, and you will lose your lucrative criminal enterprise and probably your life.

The Venezuelan army also loosely controls a slew of pro-Maduro para-military groups known as Colectivos. Should the democratic opposition come out of hiding, the Colectivos, little more than gangs, could be counted on to viciously suppress them even though a majority of Venezuelans support a return to democracy.

In view of the human rights abuses by the Venezuelan government, the worst in the Americas, pressuring Maduro to step down is not wrong. Just like toppling Saddam Hussein was not morally wrong.

The problem lies in the dubious rationales and reckless implementation that inevitably lead to massive cost in blood and treasure.

US hubris and search for quick solutions tend to set in motion unintended consequences that make things far worse. Regime change in Venezuela would be even harder than Iraq and lock the US into another forever-war and nation-building trying to fix the broken pieces. But that has not slowed down the Trump administration’s obsession with of replacing the current government with a more pro-American one.

It appears that the US is in the advanced “mission creep” stage where strikes on skiffs and tanker seizures are just not producing the results desired. That’s when military leaders typically call for more resources and wider latitude to neutralize the enemy or at least show tangible gains. In this case, the call may be for more combat ready troops to land and hold ground somewhere in Venezuela. But more resources to escalate the fight will not alleviate the Trump administration of its no-win position.

On the one hand, the large US presence and actions in the Southern Caribbean compels action to save face and show that Americans don’t back down to anti-American tinhorn dictators . On the other hand, the uncertainty of success and risk of catastrophic failure demands restraint.

The US would have a hard time controlling the country even if they threw in 50,000 troops with massive logistical backing. Still, Trump might wake up in the middle of the night in a moment of insanity and decide to invade on a whim because “national security” (and his ego) demands it. Or maybe he will need a distraction from a particularly bad news cycle. Though less likely than other scenarios, we cannot rule out him setting in motion a cascading disaster that would tear both Venezuela and the US apart. One can only hope that American general/flag officers would step in and say “No!” even if it meant the end of their careers.

The only viable options open to Trump at this point are to bomb Maduro out of power or negotiate with him.

Let’s look at the first option. If Maduro is killed, captured, or flees into exile, senior commanders would take over and rule by decree. Trump would have to negotiate with them. They might talk, but nothing would really change because they aren’t going to give up power or corrupt influence that generates wealth.

Now, there is a chance that without Maduro, the cohesive figure holding the generals together, might fray. In that case, we could see them fight each other over turf that would ultimately lead to a military version of gang warfare across the country. And that would almost certainly trigger a massive humanitarian crisis with millions more fleeing the country, along with the specter of famine and disease streaming in realtime for the world to watch. Oil production would come to a near halt. A bloody lawlessness would prevail even if some general managed to carve out enough control to claim authority to govern the country.

In this possible scenario, the transnational criminal gangs have the most to gain as they could set up hubs to ratchet up narcotics operations in South America and Caribbean islands, which until now have been minor. These gangs, working with generals and remnants of the Colectivos, would be in a position to ship far more drugs into the US. The irony is not lost.

The second option of Trump and Maduro negotiating may be more likely. Maduro knows he holds some high cards because of the extreme challenges of an American invasion, and that the clock is ticking in his favor. The US can’t linger off the coast of Venezuela forever. Maduro is quite aware that Trump is anxious for an out where he can show some kind of win that can be spun and sold to his base.

That’s when Maduro might throw a bone and agree to reduce shipments of oil to China and Cuba and sell more to the US. He could promise to clamp down on drug trafficking (the ostensible reason for US presence in the Southern Caribbean). And Maduro could toss in a contract for a big American oil company. (Trump likes business deals, especially if he or his family or cronies can benefit.) It would take a lot of spin, but Trump could declare victory of sorts and order the ships to sail away while threatening to return if Venezuela does not comply. And Maduro could hang on to power and continue to rule with an iron fist.

Meanwhile, while this limited US incursion plays out, things can still veer wildly out of control and wreak havoc.

For example, the US ship-boarding team that seized the oil tanker “Skipper” last week puts the ship at greater risk of running aground or exploding if they don’t ensure that crews properly monitor operations. According to a tanker expert, this means maintaining the inert gas system to maintain a non-explosive atmosphere in the cargo tanks. That’s in addition to keeping the main engines and generators operational. If these fail, the ship is immediately in peril of an accident. This “vintage” (20+ years old) ship sailing under a false flag (Guyana) with an unknown call sign that may not have met scheduled maintenance inspections hardly inspires confidence.

But once the US team takes command of the ship, they are responsible, even if the capabilities of the crew and the ship itself are below standard. Complicating the matter further, a heavily laden very large crude carrier (VLCC) such as the “Skipper” differs significantly from US Navy or Coast Guard vessels. Therefore, a Navy or Coast Guard officer of the deck (OOD) placed in command of a VLCC will not know how to safely operate it unless he or she has had merchant marine training and experience.

Hopefully, the US has planned ahead for a seizure of one of the world’s largest crude tankers and can quickly insert the necessary nautical expertise. But so far, all we have seen is dramatic video of a special operations team repelling on to the deck from a helicopter and taking over. Now what?

It’s not hard to imagine a nightmare accident that spills a couple of million barrels of crude oil into the Caribbean Sea that sloshes on to island beaches. Such a disaster would kill off tourism revenue and sink island economies. The clean-up and compensation costs to the US would be enormous. And the resentment sure to be stoked could turn some island-nations away from the US and induce them to cast their lot with US adversaries—setting in motion a whole new set of consequences for the region.

US Ratchets Up Caribbean Presence

December 1, 2025 / Ben Stubenberg / 0 Comments

The U.S. Navy destroyer USS Gravely (DDG-107) approaches Port of Spain, Trinidad

As the US military saber rattling escalates against Venezuela, including closing the country’s airspace, the US is pushing Caribbean island-nations for greater security cooperation. Notably, US Department of Defense officials have been holding high level talks with Trinidad & Tobago and the Dominican Republic to provide access to military bases, ports and airports.

The American pitch is framed as a larger partnership strategy to counter narcotics trafficking through the Caribbean. But these anti-drug trafficking overtures cannot be separated from the prospect of forcing regime change in Venezuela. All of which is looking more like a grandiose US geopolitical game plan for the region with hazy the objectives.

It is plausible that drug traffickers might be changing their modus operandi by applying high tech methods to better conceal their boats and using different routes to reach the US. And this should compel a more aggressive US response. However, details of a more sophisticated drug trafficking threat have not been presented or openly discussed. If drug traffickers really are shifting their tactics and upping their game, then why is the response confined to blowing up open skiffs powered by outboard motors off the coast of Venezuela (along with boats off Central America on the Pacific side) ?

Are these skiffs just easy pickings to allow some visible “wins” (or cheap thrills) for the flotilla gathered in the Southern Caribbean? If so, it begs the question: Why can’t the biggest and most lethal armed force the world locate and intercept the dangerous boats supposedly sneaking their way north up the chain of islands? The capture of just one high-tech boat with crew intact (not stupidly blowing it up and killing everyone) could go a long way to show the serious threat of drug trafficking across Caribbean waters. And certainly more believable than blasting away small boats off the Venezuelan coast alleged to be carrying drugs but never proven.

Without more evidence of drug trafficking from boats, high-tech or otherwise, the over-arching justification for massive American military presence smacks of the “weapons of mass destruction” claim that propelled the US into Iraq almost a quarter century ago. The current US claims may well cause some island-nation leaders to wonder just what they are being asked to sign up for and the price. And what is the bigger American agenda?

Now, an expanded American engagement with the Caribbean could be a good thing and become a force-multiplier. Not just to help counter drug trafficking but also gun smuggling, human trafficking, and transnational crime generally throughout the region. American initiatives could also pave the way for more cooperation to beef up Caribbean armed forces to combat gangs, particularly in Haiti, but also on other islands. Enhanced collaboration could also be combined with investment incentives, trade barrier reductions, and disease eradication programs to further strengthen institutions and goodwill. A robust and symbiotic American presence comes with the added bonus of keeping adversaries like China, Russia and China at bay.

Instead, the current proposed partnership appears to be limited to using Caribbean islands for expanded American military presence. That raises suspicions among Caribbean people and their leaders, as they are all too familiar with American troops occupying island-nations and dictating terms since the early 1900s. Moreover, it invokes the long legacy of colonial rule that resides deep in the Caribbean heart.

Current negotiations with Caribbean governments might be limited to conducting US operations in national air space and territorial waters, as well as parking spots for planes, ships, and radars. Intelligence sharing is also likely part of the package. But all that will raise concerns about sovereignty and strings attached. It’s a delicate balancing act for the island-nations that lends itself to pragmatism. But greater confidence and assertiveness among Caribbean countries and a wariness about the costs vs benefits could temper US ambitions. If there is going to be amped up cooperation, Caribbean island-nations will want to bargain as equals, not junior associates.

Indeed, questions about American intentions regarding regional engagement may have become more concerning by the troubling revelations in the Washington Post on Nov 28, 2025. The article states that after the first skiff off Venezuela was hit with eleven people on board in September, two people miraculously survived. It is unclear whether Secretary of Defense Pete Hegseth, who was watching the first strike, gave the order to kill two survivors clinging to the smoldering wreck or if he just said “kill the all.” Regardless, Admiral Frank “Mitch” Bradley, Special Operations Command, gave the direct order to blow up the last two survivors as well. Unreleased video of the survivors purportedly shows them desperately clinging to debris and trying to overturn the severely damaged boat for 41 minutes.

There is no justification for killing people on a boat, even a suspected drug boat, that does not pose a threat. Killing survivors struggling in the water is even more heinous and clearly a war-crime by any US or international legal standard (spelled out in the Geneva Convention) and possibly murder. That heinous act, if proven true, thus presents another dilemma for Caribbean leaders: Do they want to align themselves with a US leadership that so callously disregards human life> Especially when the only ones killed are on the lowest rung on the drug trafficking ladder, the desperate ones trying to make a few hundred dollars for driving a boat?

The Trump administration’s bellicosity and lawlessness today may well cause some Caribbean countries to back away from American cooperation, even with the US dangling partnership enticements. That erosion of trust and unravelling of American goodwill could turn parts of the Caribbean against the US and leave the region more fractured, impoverished, and unstable.

On a personal note, as a longtime Caribbean observer and resident, it deeply pains me to see my country spiraling downward and erasing the qualities that once defined it as a force for good in the world, however imperfect. That said, I am confident that Trump’s pigheaded and toxic approach to the Caribbean, and just about everything else this administration touches, will change. Stay tuned for a post-Trump era for the region could look like.

Southern Caribbean–What Next?

November 24, 2025 / Ben Stubenberg / 0 Comments

USS Gerald R. Ford

Time to draw upon my years in Department of Defense and weigh in on the massive US military buildup in the Caribbean and potential conflict with Venezuela.

First, let’s dispense with the “stopping the flow of drugs into the US” the “narcoterrorism” labels as justification. The drug flow from Venezuela into the US is relatively minimal compared to Mexico and Colombia. And blowing up small skiffs that may or may not have drugs and killing everyone smacks of extra-judicial killings and likely a warcrime. And that in turn puts US military personnel in grim quandary about what exactly they should or should not be doing.

Moreover, drone attacks that kill those on board is plain stupid and counterproductive. That’s because those on board could have been taken into custody and interrogated. From them the US could learn the modus operandi, production locations, transport hubs, and drug lords directing the enterprise. It’s called basic intelligence collection and could yield a great deal of information that would actually matter in the war on drugs–if that was the aim. And, by the way, the drugs could be seized and shown off to the world as evidence. But none of that is happening.

So what else is going on? Tragically, it’s more about hubris–the notion that the US can force regime change with military might, settle scores, and show them who’s boss. Most of the time, that does not work out well, especially when it comes to bigger countries. Think Vietnam, Iraq, Afghanistan. Venezuela is a large country with high mountains, dense jungles, and around 30 million people, most of them hungry and hurting. The risks of failure are huge. In the past half century, the US has tended to win the battles, but lose the wars in the big countries. That’s mainly because American people don’t like the massive price tag in blood and treasure that comes later for wars that marginally matter to US security. Moreover, the powers in charge of winning–flag officers and senior intelligence officers–have displayed little interest in grasping the complex cultural, historical, political, and sociological elements that define a country and what the US is up against.

(Caveat: Elite US Special Forces and a few intelligence officers do immerse themselves in the country the US attacks or intervenes. They take the time to learn what’s happening on the ground and how it fits into the larger picture. But their often insightful observations are seldom acted upon.)

Now, this is not to say that Americans are wrong to want to depose despots who torture and kill opponents while aligning themselves with other oppressive despots. No democratic, law-abiding country should turn a blind eye to governments who commit atrocities. Venezuela’s “President” Nicolás Maduro falls into this category. He blatantly stole the 2024 presidential election and forced the opposition to flee or go into hiding. Notably, his popular opponent Marina Corina Machado won the 2025 Nobel Peace Prize for her courage. Maduro and his henchmen’s crimes against humanity, including torture and disappearances, are the worst in the Americas. Shed no tears if he gets ousted.

The problem is that American motives in this case are not rooted in liberation and human rights but rather an ill-advised power play to assert greater dominance in the region by force. By ramping up lethal forces in the Southern Caribbean, the US has placed itself in a no-win situation that will not end well. Trump has invested too much in this misadventure to back down now. Especially after designating Maduro and his government allies as members of the so-called foreign terrorist organization Cartel de los Soles (Cartel of the Suns). More than a dozen warships, including the world’s largest aircraft carrier, the USS Gerald R. Ford, with 70 fighter jets and 2200 Marines on board, have been deployed. Most are hovering off the coast of Venezuela. In addition, numerous bombers and surveillance aircraft have been moved to the region and are flying patrols along Venezuela’s territorial waters.

This sets up a stand-off with one of two possible outcomes: Maduro steps down–an unlikely scenario–or the US strikes at targets in Venezuela. Trump is not going to leave without some kind of “win” to brag about. The unknown is what targets the US will hit. The US could bomb a few Venezuelan military bases and maybe some drug production facilities hidden in the jungle, declare victory, and go home. But Maduro could also declare victory, claiming the Americans dared not do more. And he would still be in power.

That raises the specter of going after Maduro himself and “finishing the job.” That possible scenario would trigger a free-for-all in Venezuela that would almost certainly plunge the country into a calamitous conflict. Perhaps an all-out civil war with various factions vying for power, including ambitious generals. The opposition movement to Maduro would come out of hiding and claim its mantle as the legitimate rulers, perhaps in alliance with one of the military factions.

And then there are the criminal gangs, some affiliated with the military, who would simply move in and stake out their territory. In fact, I would lay bets on ruthless gangs coming out on top since they already have powerful weapons, a stream of cash, and an established infrastructure. Once ensconced, they will be hard to dislodge and turn the fragile country into a series of warring criminal fiefdoms. Venezuela will be a state in name only.

Of course, a Venezuela thrown into chaos would not just strengthen the hold of drug trafficking gangs, but lead to widespread famine, disease, and violence that could also trigger another wave of fleeing refugees. Moreover, Venezuela’s crisis could spill over into other Caribbean countries, many of them already fragile and vulnerable, with unknown consequences. America has built up goodwill and soft power over decades of cooperation in the Caribbean. This includes cooperation with the US Coast Guard to counter narcotics and human trafficking, as well as substantial disaster assistance among other initiatives. Also, Miami is widely seen as a commercial and, to some extent, a cultural capital of the Americas where ideas and people can mix and thrive freely. But a US strike against Venezuela–with videos of civilian carnage–could well spark sympathy and solidarity with a besieged Venezuela and foment anti-American sentiment. The instability generated in Venezuela and Caribbean islands would almost certainly embolden US adversaries to go from a toe-hold to a foot-hold in the region.

In short, Trump’s US military incursion will create exactly the opposite of its intended effect by weakening US national security and leaving a lasting legacy of anguish and suffering that Americans will all pay for–heavily, again. As I write this, news outlets report on possible talks between Trump and Maduro and speculation on a diplomatic solution. I’m skeptical, but here’s one scenario: Maduro promises to stop narcotics trafficking from Venezuela that Trump can call a win, however meager. Given Trump’s susceptibility to flattery, inclination to switch positions, and suddenly cave after tough talk, Maduro has chance to call off the dogs and remain a tyrant.

Stay tuned for next posting: Envisioning a post-Trump Caribbean region that rethinks everything.