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Timeline of Trump’s Nine-Year Onslaught Against Maduro’s Venezuela Aimed at Regime Change

Trump Venezuela oil

Trump Venezuela sanctions Donald Trump’s War Against Venezuela and Nicolás Maduro which has now led to the capture of the Venezuelan president has been ongoing since 2017 with the US president insisting on a regime change

2017 – Sanctions and Isolation

In August 2017, the Trump administration imposed its first major financial sanctions on Venezuela, barring the government and state oil company PDVSA from accessing U.S. financial markets.

The U.S. declared Maduro’s government illegitimate, citing flawed elections and democratic backsliding.

2018 –  Contested Elections

In May 2018, Maduro won re-election in a vote widely criticised by the U.S., EU, and Latin American governments as neither free nor fair.

Trump responded with expanded sanctions, including restrictions on Venezuela’s cryptocurrency, the Petro.

2019 – Regime Change Push

In January 2019: The U.S. formally recognised Juan Guaidó, leader of the National Assembly, as Venezuela’s interim president, calling Maduro a usurper.

The U.S. effectively cuts off Venezuela’s oil exports to the American market, freezing PDVSA assets and revenue.

Things escalated when U.S.-backed aid convoys attempt to enter Venezuela from Colombia and Brazil; Maduro blocked them, accusing Washington of using aid as a pretext for intervention.

In April 2019, a failed military uprising backed by Guaidó and supported by the U.S. exposed the limits of Washington’s influence over Venezuela’s armed forces with senior Us officials, including John Bolton and Mike Pompeo, repeatedly stating that “all options are on the table,” including military force.

2020 – Maduro Indictments

In March 2020, The U.S. Justice Department indicted Maduro and senior officials on narco-terrorism charges, offering up to $15 million for Maduro’s arrest.

Additional sanctions were imposed on shipping companies and foreign firms accused of helping Venezuela evade oil restrictions.

In May 2020, a botched mercenary incursion involving U.S.-linked security contractors further heightens tensions, though the Trump administration denied direct involvement.

2021 – Final Trump Measures

Trump maintained sanctions until leaving office in January 2021, with Venezuela remaining one of the most heavily sanctioned countries in the world.

However, Maduro remained in power.

Trump’s Second Tenure – Since 2025

Trump began his second term with Venezuela high on his foreign policy agenda, following Maduro’s contested 2024 re-election, widely rejected by the U.S. government as fraudulent.

March 2025

Trump signed Executive Order 14245, imposing 25% tariffs on all goods imported into the U.S. from countries that import Venezuelan oil, signaling an escalation of economic pressure beyond direct sanctions on Caracas.

Throughout Q1–Q2 2025, the U.S. designated Venezuelan criminal organizations like Tren de Aragua and the Cartel de los Soles as foreign terrorist organisations and moved to deport alleged members under wartime legal authority.

U.S. policy also rescinded certain protections for Venezuelan migrants (e.g., temporary immigrant legal status), tightening immigration enforcement.

September 2025

The U.S. carried out armed engagements on the high seas against fast boats it claimed were trafficking drugs from Venezuelan territory. This marked a significant escalation from sanctions to kinetic military action.

September–October 2025

Venezuelan President Maduro warned of retaliation and defence measures as U.S. warships and Marines deployed in the Caribbean and North Atlantic waters in what independent analysts described as the largest U.S. naval presence near Venezuela in decades.

In September 2025 Maduro sent a letter to President Trump seeking direct dialogue, rejecting allegations of drug trafficking and inviting frank discussion, though no summit is scheduled.

November 2025

In November 2025, Trump and Maduro reportedly spoke by phone with Trump allegedly delivering a blunt ultimatum for Maduro to relinquish power, offering safe passage if he steps down.

Maduro rejected, instead issuing his own conditions for amnesty and sanctions relief.

The U.S. responded by positioning major naval assets including aircraft carriers off Venezuela’s coast and publicly stated Venezuelan airspace is “closed,” creating a de facto blockade.

November–December 2025

Trump publicly authorized strikes on what the U.S. government claims are drug-loading facilities and suspected trafficking vessels, some described as CIA drone operations or U.S. military actions.

In December 2025, the U.S. increased pressures including sanctions on companies shipping Venezuelan oil, intensifying actions against Caracas’s remaining revenue streams.

Some U.S. lawmakers called for a War Powers resolution to constrain Trump’s ability to initiate hostilities against Venezuela without congressional approval.

January 2026 –  Reported Regime Capture

On January 3, 2026, The United States conducted large-scale military strikes on Venezuelan territory, including in Caracas, according to news agencies reporting on Trump’s statements.

President Trump announced Venezuelan President Nicolás Maduro and his wife have been captured and flown out of Venezuela, to face U.S. legal proceedings, representing an outright regime overthrow.

The Venezuelan government condemned the strikes as military aggression, declaring a state of emergency, and vows mobilisation marking the most significant U.S.–Venezuela crisis in modern history.

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