Señor, señor
Can you tell me where we’re headin’?
Lincoln County Road or Armageddon?
Seems like I been down this way before
Is there any truth in that, señor?
This story does not relate to Bob Dylan’s cryptic and nihilistic Señor (Tales of Yankee Power), from Street Legal (1978). As for the meaning of his song, well, that’s pretty hard to fathom. A cowboy fever dream, perhaps; one of those strange illusions you channel in the early morning between sleeping and waking, more about mood than meaning.
Rather, these tales refer to the United States’ troubled and troublesome historical and contemporary relationship with its Central and Latin American neighbours – and particularly, to its current crusade against Venezuela’s autocratic president Nicolás Maduro. And it is less about Venezuela than about the US itself – an empire in all but name struggling to recover its own reflection in the shifting mirror of history. The restless ghost of Manifest Destiny is still pacing the corridors of the West Wing and the State Department. The “tales of Yankee power” keep repeating because the empire cannot imagine itself without them. Each show of force, each threat of “covert operations” is a reassurance ritual, a way of proving that the old muscles still work. But as with all empires in decline, the performance reveals more fragility than strength. The Monroe Doctrine once kept others out; the Neo-Monroe Doctrine may exist only to convince America that it is still in.
In That Howling Infinite has walked this road before in a 2017 post also entitled Tales of Yankee Power, a feature on American songwriter Jackson Browne‘s1986 album Lives in the Balance. At the time critics reckoned that its contemporary content, the USA’s bloody meddling in Central America, limited its appeal and long-term significance. And yet, here in the early twentieth first century, where the wars of the Arab Dissolution dragged the world into its vortex, and Vladimir Putin’s invasion of Ukraine ended seventy five years of Pax Europa, the Great Power politics and proxy wars that taxed intellectual and actual imaginations in that seemingly distant decade jump back into the frame like some dystopian jack in the box. As Mark Twain noted, “history doesn’t repeat itself, but it does rhyme”.
Eight years after the original Tales of Yankee Power, the story hasn’t ended – it’s simply changed key. The Uncle Sam is still abroad, still restless, still convinced the hemisphere cannot manage without his supervision. Only the script has been updated: what was once called the Monroe Doctrine is now “neo”; what was once the “war on communism” is now the “war on drugs”. But the music is familiar – and derivative: in this sad world, whenever Uncle Sam (or Comrade Ivan for that matter) plays his hand, something wicked this ways comes. As Canadian songwriter Bruce Cockburn, who also condemned the North’s intervention in the politics of the South once sang, “Little spots on the horizon into gunboats grow … Whatever’s coming, there’s no place else to go, waiting for the moon to show”.
Donald Trump’s Neo-Monroe Doctrine
Yanqui wake up
Don’t you see what you’re doing
Trying to be the Pharoah of the West bringing nothing but ruin
Better start swimming
Before you begin to drown
All those petty tyrants in your pocket gonna weigh you down
Bruce Cockburn, Yanqui Go Home (1984)
Which brings us to American journalist John Masko’s insightful analysis of Trump’s Latin American policy in a recent Unherd article. It is sharp and well-informed, particularly his framing of the “Neo-Monroe Doctrine” as the ideological scaffolding for Washington’s renewed interest in its southern backyard. Yet, like most American commentators, he skips over a crucial subplot – namely, the role of the United States itself in creating the very chaos it now claims to correct. Venezuela’s “descent into shambles,” as he calls it, did not occur in a geopolitical vacuum. Sanctions, economic strangulation, and decades of covert interference were not incidental background noise but deliberate acts of policy – the slow throttling of a regime that refused to align with the hegemon’s economic and political script. Without that context, the narrative too easily morphs into a morality play about Latin American incompetence, when in truth, it’s an old imperial story of cause, consequence, and selective amnesia.
Masko’s central thesis – that Trump has revived the Roosevelt Corollary to the Monroe Doctrine – is persuasive. In Trump’s mind, security begins at home and radiates outward; when weak or corrupt neighbours threaten that security, they must be coerced or replaced. The author rightly traces this logic back to Roosevelt’s 1904 declaration that the US would “police” the Western Hemisphere, supposedly without territorial ambition but with the clear intent of monopolising intervention. From Cuba to the Dominican Republic, Guatemala to Chile, the Corollary became the moral fig leaf for American coups, invasions, and corporate extractions. Trump, Masko argues, sees himself as restoring that prerogative – a hemispheric sheriff cleaning up the neighbourhood after decades of liberal hand-wringing.
There is, however, a deeper irony in Masko’s framing. He presents Trump’s military buildup around Venezuela – F-35s in Puerto Rico, B-52s off the coast, CIA “covert” operations loudly proclaimed on television – as a return to historical normalcy, a reassertion of superpower swagger. But this conveniently ignores that America never really stopped intervening. From Plan Colombia to the Contra wars, from IMF leverage to trade sanctions, the methods simply evolved. The empire modernised; the mission never changed.
Masko paints Venezuela as a nation hollowed out by corruption, its military loyal only through fear and patronage, its once-mighty oil industry captured by criminal syndicates and foreign proxies. He’s not wrong — but he omits the pressure points that made reform or recovery almost impossible: the freezing of foreign assets, oil export bans, and a sanctions regime designed to collapse the economy under the banner of “democracy promotion.” The result is a country starving under siege, then blamed for its own starvation. It is the oldest of imperial tricks: break it, then call it broken.
The author is also curiously incurious about the demand side of America’s perpetual Latin drug war. He notes Trump’s pretext of “narco-trafficking” but fails to mention that the real market for those drugs lies not in Caracas or Bogotá, but in Chicago and Miami. As long as there is insatiable appetite and profit north of the Rio Grande, cartels will thrive no matter how many “suspect vessels” are blown out of the Caribbean. America’s own prohibitionary puritanism – the same logic that gave birth to Al Capone – continues to nourish the problem it claims to fight.
Masko’s analysis of Trump’s strategy does capture one key insight: the re-militarisation of hemispheric policy as a form of domestic theatre. Trump’s “Neo-Monroe Doctrine” is less about Venezuela per se and more about a symbolic restoration of dominance. It is the same playbook that guided the 1989 invasion of Panama, when Noriega — once Washington’s man in the canal zone – became inconvenient and was duly removed under the banner of anti-narcotics and democracy. The echo is unmistakable. Venezuela today serves as both scapegoat and proving ground: a chance for Trump to replay history, cast himself as the avenger of American sovereignty, and perhaps even seize a few oil fields in the process – though that, as always, is to be disavowed in polite company.
What Masko misses, perhaps by design, is the wider economic and ideological dimension. To call this merely an attempt to “seize Venezuelan oil” is too simple – Trump’s doctrine is more performative than acquisitive. It is about reasserting that the Western Hemisphere remains, in practice if not in name, America’s exclusive zone of influence, a region where Chinese investment and Russian advisors are not just economic competitors but existential affronts. In that sense, the “Neo-Monroe Doctrine” is less a new foreign policy than a nostalgic hallucination: the dream of a hemisphere restored to its “natural order,” where Washington’s word is law and the rest are junior partners or failed states.
And yet, the danger lies precisely in that nostalgia. Venezuela’s collapse – accelerated by sanctions and corruption alike – has left it a tinderbox of criminal fiefdoms and shattered institutions. Push too hard and you get not regime change but fragmentation. The military Masko describes as Maduro’s bulwark could just as easily splinter, leaving behind a patchwork of armed enclaves and foreign proxies – a Caribbean Libya with oil rigs.
Trump, Masko concludes, is signalling not just to Caracas but to the continent: the Roosevelt Corollary is back. America will once again “help its friends and hamper its foes.” Perhaps so. But the hemisphere has changed; the hegemon’s writ is no longer automatic. China, once a distant abstraction, now bankrolls half the region’s infrastructure. Russia, Iran, and Turkey are present in the margins. The Monroe Doctrine may have been written to keep Europeans out of America’s backyard, but the world has since moved into the neighbourhood.
What emerges, finally, from Masko’s piece is a portrait not of a coherent strategy but of imperial muscle memory – the reflex to intervene dressed up as rediscovered purpose. Trump’s “Neo-Monroe Doctrine” is at once a geopolitical manoeuvre and a campaign slogan: Make Latin America Great Again, or at least make it obedient again. The tragedy, as always, is that ordinary Venezuelans – impoverished, exiled, and exhausted – will pay the price for another American morality play performed for domestic applause.
Trump is coming for Venezuela
…John Masko, Unherd 24 October
America’s foreign policy appears to have been turned upside down. In the Middle East and Far East, which have consumed most of America’s defence planning energy over the last few decades, trade wars and diplomatic negotiations have replaced shows of military power. Meanwhile, the US is stockpiling both materiel and manpower off the shores of South America to a degree unseen in many decades.
As of this week, the US had positioned 10 F-35 fighter jets in Puerto Rico, along with three MQ-9 reaper drones. More than 4,500 Marines and sailors have taken up residence at US Southern Command in Miami, Florida. Last week, President Trump publicly announced that he was authorising CIA covert operations in Venezuela, and a group of B-52 bombers flew near Venezuela’s coast. More than five suspected drug ships, some originating in Venezuela, have been interdicted and destroyed by US forces over recent weeks.
To many in the foreign policy establishment, Trump’s fixation on squeezing Venezuelan dictator Nicolás Maduro has been an enigma. He has justified the buildup on the grounds that Maduro’s regime harbours drug producers and distributors. But when Maduro has tried to satisfy Trump — even accepting planeloads of deported Venezuelan nationals from America — Trump has rebuffed him and redoubled US pressure. Perplexed analysts are asking: what exactly is Trump trying to achieve, if nothing Maduro can offer will please him? Where can this lead except to war or a humiliating walk-back?
This reveals a fundamental misunderstanding between the Trump administration and the foreign policy establishment. Rather than focusing on the near-term risks of war in Venezuela, Trump is asking a higher-order question: What is the point of being a superpower if you can’t stop your neighbours from sneaking deadly drugs and unapproved migrants across your borders?
In Trump’s understanding, security begins at home, and then extends to the near-abroad. When weak or corrupt leaders nearby threaten the stability of the US, they must be either forced to change their behaviour, or they must be replaced. This has not been US policy for several decades, but for most of the 20th century, it was. The name of this policy was the Roosevelt Corollary to the Monroe Doctrine. What Trump is signalling in Venezuela is that the Roosevelt Corollary is back.
President Theodore Roosevelt announced the Corollary in 1904 in his Annual Address to Congress. Since the presidency of James Monroe a century earlier, it had been American policy to oppose any new colonisation or subjugation of lands in the Western Hemisphere by European powers. Monroe’s policy did not, however, provide a road map for when European countries sent ships into America’s backyard to collect debts or fight wars, as occurred during the British, Italian and German blockade of Venezuela in 1902. Determined to keep European warships out of America’s near-abroad, Roosevelt declared that US policy would be to have a monopoly over policing power in the Western seas. He further declared that it was no longer the sole purpose of the Monroe Doctrine to keep Europe out of our near-abroad; the doctrine would also now be used to protect American interests more generally. He explained: “It is always possible that wrong actions toward this nation or toward citizens of this nation… may result in our having to take action to protect our rights; but such action will not be taken with a view to territorial aggression, and it will be taken at all only with extreme reluctance.”
During the ensuing decades, the Roosevelt Corollary was periodically called upon to reestablish order in Latin American war zones and to prevent the accession of regimes dedicated to, in Roosevelt’s words, “wronging” the US. The Corollary underlay the brief US occupation of Cuba, from 1906-1909, after the Spanish-American War, two occupations of the chronically unstable Dominican Republic, and support for the Contras against the Sandinistas in Nicaragua. It also inspired the CIA-supported overthrows of Guatemalan President Jacobo Árbenz following his nationalisation of United Fruit Company lands, and of Chilean President Salvador Allende as he led that country’s mining-based economy into ruin. It was also behind America’s futile efforts — through an embargo, assassination attempts, and the failed Bay of Pigs invasion — to topple Cuban communist dictator Fidel Castro.
America’s failure to overthrow Castro, coupled with the relative untouchability of many Soviet-allied Latin regimes during the Cold War period, caused the Roosevelt Corollary to fall into disuse. The liberal internationalist order that followed the Cold War further discouraged the use of hard power to overthrow regimes hostile to American interests. But in 2025, the Trump Administration seems determined to bring it back.
Within the Roosevelt Corollary (or, as I’ve been told it’s referred to within the administration, “Neo-Monroe Doctrine”) framework, some of Trump’s harder-to-figure foreign policy actions begin to make more sense. One of these is the appointment of Cuban-American Florida Senator Marco Rubio as Secretary of State, which was perplexing alongside Trump’s more provocative foreign policy nominations of Pete Hegseth and Tulsi Gabbard. But when one considers Rubio’s knowledge of Latin America and his hawkish record on Latin American dictators in the context of the Roosevelt Corollary agenda, he fits perfectly.
Then there are Trump’s recent actions toward Argentina and Colombia, both of which would have seemed peculiarly drastic in past administrations, but represent a return to a Rooseveltian approach to doing business. For Argentine President Javier Milei, a libertarian friend of the US who faces a fiscal crunch at home, Trump recently structured a $40 billion loan package and floated a huge purchase of Argentine beef, much to the chagrin of American cattle ranchers. Colombian socialist President Gustavo Petro, on the other hand, faced a cutoff of all American aid (Colombia has received $14 billion in aid since 2000) due to his failure to address Colombian drug trafficking. In a Rooseveltian world, the President wields plenty of carrots and a big stick.
In order to understand how Trump’s Roosevelt Corollary framework applies to Venezuela, we must first consider the state of the country today. Maduro’s Venezuela is a shambles by every possible metric: aside from its ruler’s personal security. Owing to a combination of mismanagement and corruption, Venezuela, once the wealthiest nation in Latin America, is now an economic basket case. Its economy is projected to contract by 3% this year, and inflation is at 682%. Venezuelan oil exports — the foundation of its economy — have declined by two thirds since 2012. As living standards and safety across the country have plummeted, nearly 30% of Venezuelans have left over the last 10 years, mostly for neighbouring Colombia, but many for the US (both legally and illegally).
Even with a hostile third of the country now gone, Maduro still received fewer votes for president than opposition candidate Edmundo González in last year’s election. While international organisations urged him to accept defeat, he declared victory and began a third term in office. Opposition leader María Corina Machado, whose exit polling efforts demonstrated that Maduro’s reelection was rigged, was awarded the Nobel Peace Prize for her efforts to fight the regime.
Yet while Maduro may be the world’s least legitimate leader, his position within Venezuela is still secure. As centuries of Latin American history have shown, military loyalty is the single most important requisite for regime security in the region. And while Maduro may have little else, he has that. As the Wall Street Journal has shown, Maduro has successfully “surrounded himself with a fortress of lieutenants whose fortunes and future are tied to his”. He has done this by imprisoning or exiling the disloyal, while encouraging the loyal to accept patronage jobs in state-run companies or payoffs from drug-traffickers to allow their shipments to pass. The result is a military that is just as fearful for the personal ramifications of regime failure as Maduro is himself. And in case Maduro’s reign of blackmail were to fail, there are Cuban counterintelligence officials and other paid spies installed in the ranks to detect any hint of insurrection. According to Edward Rodríguez, a defected former Venezuelan army colonel, snitching is richly rewarded with “jobs, money, cars and even homes” in a country where much of the population cannot consistently afford food.
With the government preoccupied by personal security and self-enrichment, it will surprise few that much of the official territory of Venezuela (precisely how much is unknown) is no longer under government control. Much of western Venezuela is controlled by Colombian drug-running and human-trafficking organisations like the National Liberation Army. And much of southern Venezuela is given over to feuding megabandas or organised crime rings — most infamously the gang Tren de Aragua, recently designated a foreign terrorist organisation by the US. The megabandashave outposts in Venezuela’s major cities, and all around the world, including in the US. One reason for Venezuela’s declining exports is that large parts of its major extractive industries — particularly mining — have been taken over by criminal enterprises whose activities occur off the books. These organisations control territory in the Orinoco Mining Arc in Venezuela’s southeast, where many of their mines are located.
Since Trump’s pressure campaign, Maduro has pumped out propaganda to recruit a citizen militia that can bolster the country’s depleted military. According to the Wall Street Journal, “on state television, radio and social media, announcers are telling Venezuelans that the U.S. is a rapacious Nazi-like state that wants to dig its claws into the country’s oil wealth but that the Venezuelan military, the National Bolivarian Armed Forces, are positioning to repel any invasion”. Maduro’s army currently numbers about 125,000 — a combination of military regulars and new recruits, so many of whom are above typical military age that they have been dubbed a “Dad’s Army” in the British press. According to recent reporting, the army is underfed, under-resourced, and has suffered from a significant brain-drain due to Maduro’s loyalty tests. Maduro reportedly also plans, in the event of invasion, on having the support of Colombia’s National Liberation Army — the least it can do for Caracas’ salutary neglect of its drug and human smuggling (whether before or after he delivers to Trump his proof that there’s no drug trafficking in Venezuela, one can only guess).
For the US, this all adds up to a puzzle: the Maduro regime’s continued existence directly hurts American interests, but the regime has hollowed out Venezuelan society and institutions to such a degree that regime change will probably result in further chaos, and very possibly a civil war — outcomes that also hurt American interests.
Trump has likely still concluded that regime change would help the US, but that to be effective, the muscle behind it will need to come from inside Venezuela itself. His military buildup is therefore an effort to pressure fence-sitters inside Venezuela’s military and underground political opposition (a group that still includes Machado herself) to provide that muscle. Perhaps if military brass begins to see that the Maduro regime’s days are numbered, their calculus on how best to preserve their own lives and careers will shift. There is also an outside chance that a skirmish with US forces, and a glimpse of the untenability of his position, might convince Maduro to resign or flee.
For the time being, direct covert action against Maduro’s person seems to be off the table. Ironically, we know this because of Trump’s highly irregular decision to broadcast his authorisation of CIA covert action to the world — meaning it would no longer be, well, covert. Trump’s threat of covert action, rather, functions as a nuclear bomb of psychological warfare, ensuring that every night for the foreseeable future, Maduro dreams of exploding cigars. Far more likely is covert action that assists in forming and resourcing opposition parties or militias, as the US has done in past Latin American revolutions. Conventional military strikes on Venezuela are possible but would need to be provoked. Conventional forces could also be deployed in ungoverned spaces against drug-traffickers, further underlining the impotence of the Maduro regime.
Where the Trump-Maduro standoff goes from here is hard to know. But the reasoning behind the buildup is abundantly clear, and it goes far beyond Venezuela’s drug distribution or human trafficking. It is a signal to the world, and to Latin America in particular, that American policy toward the Americas has changed. More precisely, it’s changed back from a policy of salutary neglect to an active posture in which American interests are stridently defended. As in the days of the Roosevelt Corollary, America will help its friends and hamper its foes. If a Latin American regime harms American interests, and regime change will improve the situation, America will not hesitate to affect its overthrow.
Venezuela resonates particularly with the original purpose of the Monroe Doctrine, which was to preclude European incursion into American waters. Venezuela is a long-term strategic partner of China, which relies heavily on Venezuelan oil and offers economic and political support to Venezuela internationally. Even as Venezuela has descended into ruin over the last few years, it has continued to serve as a beachhead for Chinese influence in America’s backyard. Just as President Monroe’s original doctrine intended to keep hostile foreign interference far away from American waters, President Trump’s updated Monroe Doctrine can do the same for America’s 21st-century threats.
Trump is likely gambling on the fact that Maduro’s fall would be universally popular. The rest of the world has watched in horror over the last several decades as Maduro and predecessor Hugo Chávez plunged their country into poverty and chaos. This means that if US pressure results in Maduro’s overthrow, Trump’s new Roosevelt Corollary will start out in the win column in the court of international public opinion. Whether the US stays in that column as it addresses challenges in Colombia, Peru and Argentina, only time will tell.
In That Howling Infinite 