The Trump - Maduro Caribbean Face Off
MT799 Authenticated | Independent Contributors Column
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Publisher’s Note:
As the Cuban Venezuelan Missile Crisis intensifies, and US President Trump applies more pressure on de facto Venezuelan President Nicolás Maduro, I asked Dr. Kenneth Dekleva, a renowned practicing psychiatrist with decades of foreign service experience profiling leaders for the US government, to share his thoughts on Maduro in the current crisis.
Dr. Dekleva is a frequent contributor to MT799. His last MT799 Authenticated piece was ‘Western Leadership Crisis as the World Burns: Who Fills the Power Vacuum?’
About the Author:
Dr. Kenneth Dekleva served as a Regional Medical Officer/Psychiatrist with the U.S. Dept. of State from 2002-2016 and is currently a Professor of Psychiatry, UT Southwestern Medical Center, CEO of Blackwood Advisory Solutions LLC, a Salzburg Global Fellow at the Salzburg Global Seminar, and a Senior Fellow at the George H.W. Bush Foundation for US-China Relations. He is the author of several novels, including The Russian Diplomat’s Wife and The Negotiator’s Cross.
The views expressed are entirely his own and do not represent the views of the U.S. Government, the U.S. Dept. of State, or UT Southwestern Medical Center.
The Trump-Maduro Face Off in the Caribbean
Following the recent designation of Venezuela’s Cartel de los Soles as a foreign terrorist organization, as was recently done to the Venezuelan transnational criminal organization, Tren de Aragua, US President Trump has created the big stick, in his carrot and stick approach towards Venezuela’s leader, President Nicolás Maduro.
As military tensions rise in the Caribbean, with the largest US military buildup since Grenada (1983), and authorized CIA covert action, President Trump has hinted at potential diplomatic talks aimed at easing tensions between Venezuela and the United States; President Maduro has also suggested diplomacy. This raises the question of whether a diplomatic solution is possible, and whether Maduro – Venezuela’s leader since Hugo Chávez died in 2013, and often underestimated by his opponents – can be negotiated with. In my opinion, the answer is ‘yes’. However, it requires a keen understanding of Maduro’s leadership style and political psychology.
Maduro’s history is well-known. A high school graduate with socialist roots, he rose through the party ranks early in his career, working first as a bus driver and unionist. After Chávez’s failed 1992 military coup, Maduro became inexorably linked with Chávez, Venezuela’s President from 1998 to 2013. Chávez, a charismatic populist, designated Maduro as his successor on his deathbed, and Maduro narrowly won a contested election in 2013.
Although often seen as lacking personality, charisma, or gravitas, despite his political background as head of the National Assembly, deputy for Chávez’s ruling party, and foreign minister, he was considered easygoing, reasonable, and negotiable early on. However, many overlooked his ruthlessness, cleverness, cunning, resilience, and cruelty, which he used to become a destructive, repressive dictator, overturning last year’s 2024 election results won by Venezuela’s opposition, led by Nobel Laureate María Corina Machado, known as Venezuela’s ‘Iron Lady’.
His socialist economic and political policies, which an ex-US intelligence official described as “dumb,” have pushed Venezuela—once Latin America’s leading economy supported by oil riches, democracy, and a prosperous middle class—into economic ruin, resulting in poverty and the largest migration - eight million people – in South American history.
Maduro now leads a vast ‘criminal state’ funded by illicit drugs, gold, and oil. He is beholden to criminal elements within the military, intelligence agencies, and transnational networks, while maintaining close ties with adversaries like Iran, Cuba, Russia, and China. Today, Maduro’s criminal activities—highlighted by the fact that the U.S. has placed a $50 million bounty on him—sustain his hold on power.
Having spent a lifetime serving in or visiting many failed states, ‘narco states,’ and dictatorships, and having studied adversary authoritarian leaders (including war criminals) such as Vladimir Putin, Dr. Radovan Karadzic, the late Slobodan Milosevic, Xi Jinping, and Kim Jong-un, as well as having a prior career as a forensic psychiatrist specializing in evaluating capital murderers, I have come to appreciate that even such individuals can be negotiated with. Such negotiations are difficult because they require understanding the worldview of leaders who have committed horrible and often evil acts in pursuit of their destructive political goals.
President Trump (author of The Art of the Deal) is known for his unconventional, bold, and intuitive approach to diplomatic negotiations. This is evident in his outreach to North Korea’s Chairman Kim Jong-un during 2018-2019, his recent trade talks with China’s President Xi Jinping, his role in brokering the Abraham Accords in the Middle East, his efforts to secure a cease-fire in Gaza, and more recently, his attempts to negotiate an end to the tragic, genocidal Ukraine war with Russia’s President Vladimir Putin. His recent hints of negotiations with Maduro have combined diplomatic outreach with a significant military buildup, intensifying pressure on Maduro. Will this US military pressure create fissures within the Venezuelan military, closely monitored by Cuban intelligence?
But Maduro’s negotiation skills also warrant closer scrutiny. In addition to rising within Chávez’s party, he served as his foreign minister for six years, traveling around the world and gaining extensive experience, including brokering a peace deal with Colombia. Earlier this year, he showed his negotiating prowess in releasing six American hostages after meeting with Trump’s special envoy Richard Grenell. Maduro even wrote a recent letter to Pope Leo IV, who has called for dialogue and peace in Venezuela, stating,
“I have great faith that Pope Leo, as I stated in the letter I sent him, will help Venezuela preserve and achieve peace and stability.”
President Trump has often shown a mix of negotiating flexibility with firm, even ‘Reaganesque,’ strategic deterrence, as demonstrated by his recent bombing of Iran’s nuclear sites. However, there are also ‘red lines’ in Venezuela that demand an immediate response. Maduro, whose exit (‘the Cedras option’ in Haiti, 1994) should be negotiated, must be given an absolute deadline to shut down the Iranian drone base and to insist that all Iranian military and intelligence ‘advisors’ leave (‘the Sadat option’ as with Russian advisors in 1972) Venezuela within 24 hours.
President Trump often sets negotiating deadlines. This past week, he issued a deadline to the wrong leader — Ukraine’s President Zelensky. Deadlines should instead be directed at dangerous, dictatorial adversaries like Maduro as clear red lines. That is the only language Maduro understands. Failing to resolve the Venezuelan crisis will cause dangerous ripple effects, weakening both President Trump and America, while also drawing close attention from our allies and rivals such as Putin, Xi, Kim, and Iran’s Supreme Leader. President Trump’s extensive military buildup, strikes on drug boats, and designation of Venezuelan criminal organizations as foreign terrorist entities have cornered Maduro. Trump has famously said (in The Art of the Deal),
“You have to know when to walk.”
But this is a deal he also cannot walk away from. And Maduro is well aware of that.
Vol 2, No 49 - BWR (MT799) 26.11.2025
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