Operation Gideon (2020)

Based on Wikipedia: Operation Gideon (2020)

A Boat, a Beach, and a Very Bad Plan

In the early hours of May 3, 2020, two small boats carrying roughly sixty men motored through Caribbean waters toward the Venezuelan coast. Their mission: to land on a beach, seize an airport, capture the president of Venezuela, and fly him out of the country. By sunrise, six men were dead, the rest were captured or fleeing, and the whole world was watching what one commentator called "the Stupid Bay of Pigs."

This was Operation Gideon.

To understand how a ragtag group of Venezuelan exiles and two former American Green Berets came to launch an invasion of a sovereign nation—a plan so doomed that even its organizers had described it as a "suicide mission"—we need to back up and meet the cast of characters. It's a story of a country in crisis, a president under siege, an opposition leader running out of options, and a private security contractor who saw opportunity where others saw catastrophe.

Venezuela: A Country on the Edge

Nicolás Maduro became president of Venezuela in 2013, hand-picked by Hugo Chávez to continue the socialist revolution that Chávez had launched in 1999. But Maduro was no Chávez. Where Chávez had charisma and oil money, Maduro had neither.

He won his first election by a razor-thin margin under questionable circumstances, and what followed was, in the words of one political scientist, "one of the most devastating national economic crises seen anywhere in modern times." Inflation spiraled into the millions of percent. Supermarket shelves went bare. Millions of Venezuelans fled the country. By some estimates, the average Venezuelan lost twenty-four pounds in body weight during the worst years of the crisis.

Maduro responded to dissent the way autocrats typically do: he cracked down. He packed the courts, sidelined the opposition-controlled National Assembly by creating a new legislature stacked with loyalists, and promoted so many military officers that Venezuela ended up with more generals than the United States—in an army one-tenth the size. The promotions weren't about military strategy. They were about buying loyalty.

The 2018 presidential election was, to put it diplomatically, "widely seen as fraudulent." That's when things got complicated.

Enter Juan Guaidó

In January 2019, a young politician named Juan Guaidó became president of the National Assembly—the elected legislature that Maduro had tried to replace. Guaidó did something audacious: he declared himself the legitimate interim president of Venezuela, arguing that Maduro's fraudulent election meant the presidency was constitutionally vacant.

More than fifty countries agreed with him, including the United States. The Trump administration threw its weight behind Guaidó, charging Maduro with narcoterrorism and offering a fifteen-million-dollar bounty for information leading to his arrest. For a moment, it seemed like change might actually come to Venezuela.

It didn't.

Guaidó attempted an uprising on April 30, 2019. It fizzled. He had bet that enough of the military would defect to tip the balance. Some did—but the senior officers, the ones who controlled the tanks and the troops, stayed with Maduro. Within hours, Guaidó was back where he started: recognized by the international community, but powerless to do anything about it.

This left Guaidó and his mentor, the opposition leader Leopoldo López, in an impossible position. They were the internationally recognized government of a country they didn't control. They had no army, no police force, no ability to collect taxes or enforce laws. They were, essentially, a government-in-exile that hadn't left home yet.

According to sources who spoke to The Wall Street Journal, López and his closest aides began looking for other options. They started meeting with private military companies. They contemplated hiring mercenaries.

The Two Men Who Made It Happen

Clíver Alcalá Cordones had once been a Major General in Venezuela's army, close enough to Chávez that he was practically part of the furniture. But he'd broken with Maduro in 2013 and fled to Colombia, where he began gathering other military defectors around him. By 2019, he had established training camps on the La Guajira Peninsula, near the Colombian city of Riohacha, where several hundred Venezuelan exiles were preparing for... something.

Alcalá had a plan. He would lead his men across the border into western Venezuela, capture the oil center of Maracaibo, and fight their way to Caracas. He called it a "mad plan," and he wasn't being modest. He was being accurate.

There was a complication: in 2011, the United States had charged Alcalá with providing weapons to FARC, the Colombian guerrilla group. In March 2020, he would be indicted for narcoterrorism as part of something called the Cartel of the Suns. The man recruiting fighters to restore democracy in Venezuela was also allegedly a drug trafficker.

Then there was Jordan Goudreau.

Goudreau was a Canadian-born American citizen who had served in the U.S. Army Special Forces—the Green Berets—reaching the rank of Sergeant First Class before retiring due to injuries. In 2018, at age forty, he founded a private security company called Silvercorp USA. The company's original business model was unusual: Goudreau wanted to embed counter-terrorism agents in schools, disguised as teachers.

That didn't work out, so Goudreau pivoted. In February 2019, his company provided security at Venezuela Aid Live, a concert on the Colombian border intended to support humanitarian aid for Venezuela. Goudreau looked at the chaos, saw the Trump administration's aggressive stance against Maduro, and spotted what he believed was a business opportunity.

According to his friend and business partner Drew White, Goudreau became convinced that overthrowing Maduro could be profitable. White distanced himself from the company when Goudreau started talking about launching military operations. As it turned out, this was a wise decision.

The Connection

How did a Venezuelan general on the run and an American ex-Green Beret with a fledgling security company end up working together? The answer involves political fundraisers, luxury hotels, and a man who used to guard Donald Trump.

Goudreau knew Keith Schiller, who had been Trump's longtime director of security before briefly serving in the White House. Schiller brought Goudreau to a March 2019 fundraising event in Washington, D.C., focused on security in Venezuela and investment opportunities that might arise once Maduro was gone. It was held at the University Club, the kind of place where people discuss regime change over cocktails.

At the event, Goudreau met Lester Toledo, who served as director of humanitarian aid for Guaidó's shadow government. A few weeks later, Toledo introduced Goudreau to Alcalá at the JW Marriott in Bogotá.

The meeting was revealing. Alcalá described his forces: three hundred men, he claimed, ready to launch his "mad plan" across the border. Goudreau looked at the actual numbers and saw something different. There weren't three hundred fighters. There were sixty.

Goudreau proposed an alternative. Instead of a conventional invasion, Silvercorp would train and equip the men for a rapid strike—a surgical operation to capture Maduro directly. The cost: one and a half million dollars.

According to The Washington Post, Goudreau told the men that they were training for a U.S.-backed incursion into Venezuela. There is no evidence that this was true. When Toledo and other Guaidó officials looked more closely at the plan, they concluded it was a suicide mission and cut off contact.

That should have been the end of it.

The Contract

In August 2019, Guaidó established something called the Strategic Committee and put a man named J. J. Rendón in charge. Rendón was a controversial political strategist who had worked campaigns across Latin America. His job was to explore every possible option for removing Maduro from power, from diplomatic pressure to military action.

Rendón's committee reviewed the legal justifications for regime change. They concluded that the Venezuelan Constitution, the United Nations Convention against Transnational Organized Crime, and various international treaties provided cover for what they were contemplating. They also reviewed bids from private military companies—at least six, according to The Wall Street Journal—each offering to enter Venezuela, encourage a military rebellion, and overthrow Maduro.

In September 2019, Goudreau made his pitch to Rendón. The plan had evolved: Silvercorp would capture Maduro and other high-level officials and extract them from Venezuela. The cost had also evolved—up to $212.9 million. Goudreau claimed the operation would be "self-financed," though how he planned to finance a quarter-billion-dollar military operation remains unclear.

What happened next is disputed. According to documents that later emerged, Guaidó's representatives signed a contract with Silvercorp. According to Guaidó, no binding agreement was ever reached. What is not disputed is that Goudreau believed he had a deal, and that he continued planning the operation as if he did.

There's a footnote worth mentioning: Goudreau's lawsuit, filed in October 2020, claimed that Erik Prince—the founder of Blackwater, the most notorious private military company in American history—had submitted a competing proposal. Prince's plan allegedly called for five thousand troops and mercenaries at a cost of five hundred million dollars. Prince denied this, as did Guaidó.

Meanwhile, Everyone Was Watching

One of the remarkable things about Operation Gideon is how many people knew about it before it happened.

Venezuelan intelligence had infiltrated the operation from the beginning. Diosdado Cabello, one of the most powerful figures in Maduro's government and the head of the ruling party, had sources inside the training camps. He would later display captured weapons and documents on Venezuelan state television, clearly prepared for exactly this moment.

The Associated Press also knew. Journalists had been tracking the plot for months, interviewing participants and reviewing documents. The AP published an exposé on May 1, 2020—two days before the boats launched. The story revealed the plan in detail: the training camps, the weapons purchases, the Silvercorp connection, everything.

The Colombian government knew. Alcalá had approached Colombia's National Intelligence Directorate in June 2019, asking for support and claiming (falsely) that Goudreau was a former CIA agent. According to one account, former president Álvaro Uribe and then-president Iván Duque expressed support for the operation, offering a training camp and an airstrip in exchange for help combating leftist guerrillas in the area.

The U.S. government knew too. Officials had learned about the Venezuelan defectors gathering in Colombia and discussed plans to redirect them toward humanitarian work—helping with the refugee crisis rather than planning an invasion. When reports emerged that they might be used for a military operation, an anonymous U.S. official described the idea as "completely insane."

The CIA contacted officials in Bogotá to clarify that Goudreau had never been a CIA agent, which is the intelligence community's way of saying: this guy is not with us, and we don't want to be blamed for whatever happens next.

Three Different Operations

Sebastiana Barráez, a journalist who specializes in Venezuelan military affairs, argues that what we call "Operation Gideon" was actually three different operations at different times, layered on top of each other like geological strata.

The first was Alcalá's original plan: the "mad" invasion through western Venezuela, led by the exiled general and his defectors. This phase ended in March 2020 when Alcalá was extradited to the United States on narcoterrorism charges. He turned himself in peacefully and was flown to New York, leaving his men leaderless.

The second phase began when a man named Antonio Sequea took over the camps. Sequea, a captain who had participated in Guaidó's failed April 2019 uprising, inherited a depleted force and a plan that had already been compromised. Barráez describes what came next as a "suicide mission" walking into an ambush.

The third phase was Silvercorp's involvement—and the Venezuelan government's exploitation of it. By this point, Cabello and his intelligence services knew everything. The question, which has never been fully answered, is whether they merely observed the operation unfold or actively encouraged it to proceed so they could crush it publicly.

The Equipment Problem

By mid-2019, Goudreau had compiled a shopping list of what the operation would need. According to Ephraim Mattos, a former Navy SEAL who met with Alcalá's troops while working in Colombia, the list included: 320 M4 assault rifles, an anti-tank rocket launcher, Zodiac boats, one million dollars in cash, and state-of-the-art night vision goggles.

The trainees believed they had the backing of the U.S. government. Mattos decided to check. He looked up Silvercorp on the internet. What he found was a small company website, some Instagram posts, and no evidence of the resources or connections Goudreau claimed.

"I was like, 'Guys, guys, guys, this guy is not who he says he is,'" Mattos later recalled.

Nobody listened.

The Launch

By May 2020, the operation was falling apart before it even began. Alcalá was in U.S. custody. The AP had published its exposé. The element of surprise—critical to any military operation, especially one involving sixty men against a nation of thirty million—was gone.

The plan, such as it was, called for the force to travel by boat from eastern Colombia to a beach at Macuto, a coastal town north of Caracas. From there, they would seize a nearby airfield, capture Maduro and other high-level officials, and fly them out of the country. How they planned to accomplish this with sixty men, limited weapons, and no air support against a government that knew they were coming is a question that has no good answer.

On May 3, 2020, two boats launched.

The first boat, carrying the main assault force, approached the Venezuelan coast in the pre-dawn darkness. Venezuelan security forces were waiting for them. At least six of the invaders were killed. The rest were captured.

The second boat, carrying eight men including two Americans—former Green Berets named Luke Denman and Airan Berry—fared no better. They never made it to shore. Venezuelan forces intercepted them, and both Americans were taken alive.

Within days, Denman and Berry appeared on Venezuelan state television. Their interrogations were broadcast nationally, with Maduro's government presenting them as proof of American aggression. Denman, reading from what appeared to be a prepared statement, described the operation's objectives: seize the airport, take control of the control tower, bring in a plane, "take Maduro and fly him to the United States."

The Aftermath

The Venezuelan government portrayed Operation Gideon as a terrorist invasion coordinated by Colombia and the United States. Maduro called the attackers "mercenaries" and "terrorists," and insisted the plot reached to the highest levels of the Trump administration. There is no evidence that the U.S. government sanctioned or supported the operation—indeed, available evidence suggests American officials thought the plan was crazy and tried to distance themselves from it.

Guaidó and some of his supporters suggested the whole thing was a false flag operation—that Maduro had orchestrated the invasion himself to justify a crackdown and discredit the opposition. This theory has problems: the captured Americans were real, the dead Venezuelans were real, and Goudreau was very real, giving interviews from Florida in which he proudly claimed responsibility for the operation.

Speaking of Goudreau: on the morning of May 3, as the operation was collapsing, he posted a video to social media. Standing next to Antonio Sequea, who was in Colombia rather than on the boats, Goudreau announced that the operation was underway. He called the attackers "freedom fighters" seeking to "restore democracy" to Venezuela.

The video raised immediate questions. If Goudreau was the mastermind, why was he in Florida? If Sequea was the field commander, why was he in Colombia? And if this was a coordinated military operation, why was its leader announcing it on Twitter?

The Stupid Bay of Pigs

The comparison to the Bay of Pigs—the CIA's catastrophic 1961 attempt to overthrow Fidel Castro using Cuban exiles—is inevitable but perhaps unfair to the Bay of Pigs. That operation at least had the backing of the U.S. government, even if that backing evaporated at the crucial moment. Operation Gideon had nothing comparable.

Commentators struggled to describe what they had witnessed. The words that kept recurring were: amateurish, underfunded, poorly organized, impossible, suicidal. One analyst noted that the operation had "all the hallmarks of something planned on the back of a napkin."

The participants couldn't even agree on what to call it. Was it an invasion? An infiltration? A raid? A coup attempt? An assassination plot? The Venezuelan government called it terrorism. Goudreau called it a liberation mission. Critics called it a debacle, a fiasco, a farce.

What is certain is that it accomplished nothing except getting people killed and handing Maduro a propaganda victory. The two American prisoners became bargaining chips; they were eventually released in 2022 as part of a prisoner exchange. The Venezuelan fighters who survived faced lengthy prison sentences. And Maduro remained exactly where he had been: in power, defiant, and now with proof that his enemies really were trying to overthrow him by force.

The Questions That Remain

Years later, fundamental questions about Operation Gideon remain unanswered.

Did Juan Guaidó authorize the operation, or merely discuss it before walking away? The contract that emerged appears to bear signatures from his representatives, but Guaidó has denied that any binding agreement was reached. The truth may lie somewhere in between: perhaps the opposition explored the option seriously enough to sign documents, then got cold feet, but couldn't—or didn't—stop Goudreau from proceeding on his own.

What did the Colombian government know, and when did they know it? Training camps don't materialize out of thin air, especially not camps full of foreign nationals preparing military operations. The camps operated for months. Either Colombian intelligence was asleep, or someone chose to look the other way.

How deeply had Venezuelan intelligence penetrated the operation? Diosdado Cabello clearly had advance knowledge—but did his agents merely observe, or did they encourage the operation to proceed so it could be crushed publicly? There is a difference between monitoring a doomed plot and actively shepherding it toward disaster.

And finally: what was Jordan Goudreau thinking? The man had served in Special Forces. He knew what real military operations looked like. How did he convince himself—and more importantly, how did he convince others—that sixty men with limited weapons could overthrow a government that controlled an army, a navy, an air force, and a vast intelligence apparatus?

Some observers have speculated that Goudreau was a con man who got in over his head. Others suggest he genuinely believed his own propaganda. Still others wonder if he was being manipulated by forces he didn't understand—fed misinformation by Venezuelan intelligence, perhaps, or simply too eager to believe that the opportunity of a lifetime had fallen into his lap.

The Broader Context

Operation Gideon did not occur in a vacuum. The Trump administration had spent years ratcheting up pressure on Venezuela: sanctions, diplomatic isolation, explicit calls for regime change, and that fifteen-million-dollar bounty on Maduro's head. This created an environment in which schemes that would otherwise seem ludicrous could seem almost plausible.

When the president of the United States is publicly calling for the removal of a foreign leader, when the U.S. government is offering millions for his capture, when American officials are meeting with opposition figures and discussing the future of a post-Maduro Venezuela—in that environment, it's not entirely crazy for a freelance mercenary to think he might find support for an audacious plan.

The support never materialized, but the atmosphere of possibility did. And in that atmosphere, desperate men made desperate decisions.

Venezuela remains in crisis. Maduro remains in power. The opposition has fragmented. Millions of Venezuelans have fled. And somewhere in all of this wreckage lies the story of Operation Gideon: a reminder that regime change is harder than it looks, that good intentions don't guarantee good outcomes, and that sometimes the gap between a bold plan and a suicide mission is simply a matter of perspective.