Rivalry

How the Maduro and Trump confrontation unfolded

Across two Trump terms the United States moved from sanctions on Nicolás Maduro and his government to recognising a rival interim president, indicting Maduro and, in January 2026, seizing him in Caracas. Maduro has pleaded not guilty in a New York federal court, including to a torture conspiracy charge added in October 2026, and his lawyers argue he is immune from prosecution as a head of state.

31 July 2017 to today · 40 dated events · 39 sources
Where it stands now · as of 31 October 2026

Maduro and Flores are held in a federal jail in Brooklyn and have pleaded not guilty to all charges, including a torture conspiracy charge added in October 2026. Their motions to dismiss on head of state immunity grounds are pending. Judge Hellerstein died on October 28, 2026 and Judge Analisa Torres is taking over the case, which had been set for trial on June 14, 2027.

Nicolás Maduro
🇻🇪 Side A

Nicolás Maduro

Former president of Venezuela, in US federal custody awaiting trial
Photo: Ricardo Stuckert, CC BY 2.0 (source)
VS
Donald Trump
🇺🇸 Side B

Donald Trump

President of the United States
Photo: Daniel Torok, Public domain (source)
10 : 26Moves recorded
0 : 10Sanction
2 : 6Legal step
4 : 2Statement
1 : 3Military
Overview · 31 Jul 2017 to 28 Oct 2026 · click a dot to jump
20172019202020212022202320242025202631 July 2017: US Treasury sanctions Maduro24 August 2017: Trump order limits Venezuelan state financing20 May 2018: Maduro declared winner of presidential vote21 May 2018: Trump bars purchases of Venezuelan government debt22 May 2018: Maduro expels top US diplomats23 January 2019: Trump recognises Juan Guaidó as interim president23 January 2019: Maduro breaks diplomatic relations with the US28 January 2019: Treasury sanctions state oil company PdVSA5 August 2019: Trump blocks all Venezuelan government property in the US26 March 2020: Maduro charged in New York31 January 2025: Trump envoy meets Maduro in Caracas14 March 2025: Alien Enemies Act invoked against Tren de Aragua24 March 2025: Tariff threat on buyers of Venezuelan oil25 July 2025: Cartel de los Soles listed as terrorist group7 August 2025: Reward for Maduro raised to $50 millionAugust 2025: US boosts naval forces off VenezuelaAugust 2025: Venezuela deploys troops and calls up militia2 September 2025: First US strike on a boat from Venezuela24 November 2025: Cartel de los Soles designated a Foreign Terrorist Organization29 November 2025: Trump says Venezuelan airspace should be considered closed29 November 2025: Caracas rejects airspace warning30 November 2025: Trump confirms he spoke with Maduro16 December 2025: Trump orders blockade of sanctioned oil tankersDecember 2025: Venezuela calls blockade a "grotesque threat"3 January 2026: US forces seize Maduro in Caracas5 January 2026: Maduro pleads not guilty in Manhattan5 January 2026: Delcy Rodríguez sworn in as interim president9 January 2026: Order shields Venezuelan oil revenue held by Treasury9 February 2026: Licence for Maduro's legal fees granted then revokedFebruary 2026: Defence seeks dismissal over blocked legal fees20 February 2026: Venezuelan oil tariff order ended26 March 2026: Judge says he will not dismiss the caseApril 2026: US allows Venezuela to pay Maduro's lawyers15 April 2026: Homeland Security lifts ban on direct flights22 July 2026: Trial set for June 20272 September 2026: Maduro claims head of state immunity2 October 2026: Prosecutors reject immunity claim8 October 2026: Torture conspiracy charge added15 October 2026: Maduro pleads not guilty to torture charge28 October 2026: Trial judge dies and case passes to Judge Torres
2017
31 Jul 2017
Trump Sanction

US Treasury sanctions Maduro

The Treasury Department's Office of Foreign Assets Control designated Maduro under Executive Order 13692, blocking any of his assets under US jurisdiction and barring US persons from dealing with him.

“By sanctioning Maduro, the United States makes clear our opposition to the policies of his regime”Steven Mnuchin, US Department of the Treasury
24 Aug 2017
Trump Sanction

Trump order limits Venezuelan state financing

Trump signed Executive Order 13808, barring US persons from certain dealings in new debt and equity of the Venezuelan government and the state oil company PdVSA.

2018
20 May 2018
Maduro Leadership

Maduro declared winner of presidential vote

Maduro won 68 percent of the vote in Venezuela's presidential election, with 52 percent of voters not casting ballots, Al Jazeera reported.

🇻🇪 VenezuelaAl Jazeera#
22 May 2018
Maduro Statement

Maduro expels top US diplomats

In a televised speech, Maduro gave the US charge d'affaires and his deputy 48 hours to leave Venezuela, accusing them of trying to sabotage the election.

“We've had enough of your conspiring.”Nicolás Maduro, Al Jazeera
🇻🇪 CaracasAl Jazeera#
2019
23 Jan 2019
Turning point
Trump Statement

Trump recognises Juan Guaidó as interim president

Trump said the United States was officially recognising National Assembly president Juan Guaidó as interim president of Venezuela, after the Assembly declared Maduro illegitimate.

28 Jan 2019
Trump Sanction

Treasury sanctions state oil company PdVSA

The Treasury Department designated Petroleos de Venezuela, S.A. under Executive Order 13850, blocking its property under US jurisdiction.

“Today's designation of PdVSA will help prevent further diverting of Venezuela's assets by Maduro”Steven Mnuchin, US Department of the Treasury
5 Aug 2019
Trump Sanction

Trump blocks all Venezuelan government property in the US

Trump signed Executive Order 13884, blocking US-held property of the Government of Venezuela. The order cited "the continued usurpation of power by Nicolas Maduro and persons affiliated with him."

2020
26 Mar 2020
Turning point
Trump Legal step

Maduro charged in New York

The Justice Department announced a four-count superseding indictment, unsealed in the Southern District of New York, charging Maduro with narco-terrorism conspiracy, cocaine importation conspiracy and two machine gun and destructive device counts. Prosecutors alleged he was a leader of the Cartel de los Soles. The State Department offered a reward of up to $15 million.

$15 million reward offered in 2020🇺🇸 New YorkUS Department of JusticeUS Department of State#
· · · 58 months later
2025
31 Jan 2025
Trump Talks

Trump envoy meets Maduro in Caracas

Richard Grenell, Trump's envoy for special missions, met Maduro at Miraflores Palace, and Venezuela freed six detained Americans. The White House said the trip focused on deportations and detainees.

“No. We want to do something with Venezuela. I've been a very big opponent of Venezuela and Maduro.”Donald Trump, Voice of America (Associated Press)
14 Mar 2025
Trump Legal step

Alien Enemies Act invoked against Tren de Aragua

Trump signed Proclamation 10903 invoking the Alien Enemies Act against the Tren de Aragua gang. It alleged the gang acted "at the direction, clandestine or otherwise, of the Maduro regime in Venezuela."

24 Mar 2025
Trump Sanction

Tariff threat on buyers of Venezuelan oil

Trump signed Executive Order 14245, authorising a 25 percent tariff on goods from any country importing Venezuelan oil, effective April 2, 2025.

25 Jul 2025
Trump Sanction

Cartel de los Soles listed as terrorist group

The Treasury Department designated Cartel de los Soles a Specially Designated Global Terrorist, alleging it supported Tren de Aragua and the Sinaloa Cartel.

7 Aug 2025
Trump Money

Reward for Maduro raised to $50 million

The State Department raised its reward for information leading to Maduro's arrest or conviction to up to $50 million, citing the Cartel de los Soles designation.

$50 million rewardUS Department of State#
Aug 2025
Trump Military

US boosts naval forces off Venezuela

The United States said it would strengthen its naval presence in waters off Venezuela to counter drug cartels, deploying thousands of personnel, the Associated Press reported.

2 Sep 2025
Turning point
Trump Military

First US strike on a boat from Venezuela

Trump said a US military strike on a vessel that departed Venezuela killed 11 people he described as Tren de Aragua members. Maduro did not address the strike directly, and a Venezuelan minister questioned whether the released video was genuine.

“Please let this serve as notice to anybody even thinking about bringing drugs into the United States of America.”Donald Trump, WLRN (Associated Press)
24 Nov 2025
Trump Legal step

Cartel de los Soles designated a Foreign Terrorist Organization

Secretary of State Marco Rubio's designation of Cartel de los Soles as a Foreign Terrorist Organization took effect on publication in the Federal Register. The notice does not name Maduro.

29 Nov 2025
Trump Statement

Trump says Venezuelan airspace should be considered closed

In a post addressed to airlines, pilots, drug dealers and human traffickers, Trump said the airspace above and around Venezuela should be considered closed. He later told reporters not to "read anything into it."

“please consider THE AIRSPACE ABOVE AND SURROUNDING VENEZUELA TO BE CLOSED IN ITS ENTIRETY.”Donald Trump, RTHK (AFP)
30 Nov 2025
Trump Talks

Trump confirms he spoke with Maduro

Asked whether he had spoken with Maduro, Trump confirmed a call. Reuters cited a New York Times report that the call took place earlier in November and discussed a possible meeting in the United States.

“I don't want to comment on it. The answer is yes.”Donald Trump, KSL (Reuters)
16 Dec 2025
Trump Sanction

Trump orders blockade of sanctioned oil tankers

Trump ordered a blockade of sanctioned oil tankers going into and out of Venezuela, a week after US forces seized a tanker off the Venezuelan coast. By then the US had carried out more than two dozen strikes on boats, killing at least 90 people, the Dhaka Tribune reported.

“A TOTAL AND COMPLETE BLOCKADE OF ALL SANCTIONED OIL TANKERS going into, and out of, Venezuela.”Donald Trump, Dhaka Tribune
2026
3 Jan 2026
Turning point
Trump Military

US forces seize Maduro in Caracas

US forces seized Maduro and his wife, Cilia Flores, in Caracas and took them to New York. An updated indictment made public the same day added new details and co-defendants, including Flores, Reuters reported. The Justice Department described Maduro in it as the "de facto but illegitimate ruler" of Venezuela, CNN reported.

5 Jan 2026
Maduro Legal step

Maduro pleads not guilty in Manhattan

Maduro and Flores pleaded not guilty before US District Judge Alvin Hellerstein. Speaking through an interpreter, Maduro said he had been captured at his home in Caracas and called himself a prisoner of war.

“I am innocent. I am not guilty. I am a decent man. I am still president of my country”Nicolás Maduro, RTE (Reuters)
5 Jan 2026
Leadership

Delcy Rodríguez sworn in as interim president

Maduro's vice president, Delcy Rodríguez, was sworn in as interim president in Caracas hours after the court hearing, Reuters reported. She expressed support for Maduro.

🇻🇪 CaracasRTE (Reuters)#
9 Jan 2026
Trump Sanction

Order shields Venezuelan oil revenue held by Treasury

Trump signed Executive Order 14373, declaring a national emergency over possible court seizures of Venezuelan government funds held in US Treasury accounts and directing that the funds be held pending a decision by the Secretary of State.

9 Feb 2026
Trump Legal step

Licence for Maduro's legal fees granted then revoked

The Office of Foreign Assets Control granted a licence allowing Venezuelan government funds to pay Maduro's and Flores's lawyers, then revoked it three hours later, MercoPress reported.

20 Feb 2026
Trump Sanction

Venezuelan oil tariff order ended

Trump signed Executive Order 14389, which listed the March 2025 tariff on countries importing Venezuelan oil among duties that would no longer be in effect. The order cited only "recent events."

26 Mar 2026
Ruling

Judge says he will not dismiss the case

At a hearing on March 26, Judge Hellerstein said from the bench that he would not dismiss the case, while questioning the government's basis for blocking the use of Venezuelan funds for the defence, MercoPress reported.

“I am not going to dismiss the case.”Alvin Hellerstein, MercoPress
🇺🇸 New YorkMercoPress#
Apr 2026
Trump Legal step

US allows Venezuela to pay Maduro's lawyers

Washington authorised Venezuela to cover the legal representation of Maduro and Flores, MercoPress reported.

15 Apr 2026
Trump Corporate

Homeland Security lifts ban on direct flights

The Department of Homeland Security ended its suspension of direct commercial flights between the US and Venezuela, saying Venezuela's interim government had re-established diplomatic and economic relations with the United States.

22 Jul 2026
Ruling

Trial set for June 2027

Judge Hellerstein set June 1, 2027 as the preliminary start of the trial and adopted a pretrial schedule, including a November 17 hearing on the defence's dismissal arguments, MercoPress and the Associated Press reported.

2 Sep 2026
Maduro Filing

Maduro claims head of state immunity

Maduro and Flores filed motions to dismiss, arguing they are immune from prosecution as the head of state and first lady of a foreign country. Maduro's lawyers wrote that he denies the allegations.

“No American court has ever presided over the criminal trial of a foreign leader”Lawyers for Nicolás Maduro, OPB (Associated Press)
2 Oct 2026
Trump Filing

Prosecutors reject immunity claim

In a filing on October 2, federal prosecutors argued that the 2019 US decision to stop recognising Maduro as head of state deserves "absolute deference" from the courts. They noted that the US recognises Delcy Rodríguez as head of state and that her government has not sought immunity for Maduro, The Edge Malaysia reported.

“former rogue officials of a formerly rogue state with no entitlement to immunity”US federal prosecutors, The Edge Malaysia
8 Oct 2026
Trump Legal step

Torture conspiracy charge added

The Justice Department unsealed a superseding indictment charging Maduro and Flores with conspiring to commit torture, including of US citizens, alongside the narco-terrorism, cocaine importation and weapons counts. Prosecutors alleged the pair sat atop a system of repression. The department noted that an indictment is merely an allegation.

“These additional charges against the Maduros reflect the dedication of this Administration to delivering justice for the victims of torture, narcoterrorism, and organized crime.”Todd Blanche, US Department of Justice
🇺🇸 New YorkUS Department of Justice#
15 Oct 2026
Maduro Legal step

Maduro pleads not guilty to torture charge

Maduro and Flores each pleaded not guilty to the superseding indictment. Maduro said he rejected the document and called the torture accusations false, and Judge Hellerstein entered a not guilty plea on his behalf. The judge moved the trial start to June 14, 2027, the Associated Press reported.

“I reject this document in its entirety.”Nicolás Maduro, Al Jazeera
28 Oct 2026
Legal step

Trial judge dies and case passes to Judge Torres

Judge Alvin Hellerstein, who had presided over the case since 2020, died at 92, the Associated Press reported. Judge Analisa Torres is taking over the case.

In their own words

Exact quotes, side by side

US military pressure in the Caribbean, on the day of the first boat strike

Nicolás Maduro
“In the face of imperialist threats, God (is) with us”
2 September 2025 · WLRN (Associated Press)
Donald Trump
“Please let this serve as notice to anybody even thinking about bringing drugs into the United States of America.”
2 September 2025 · WLRN (Associated Press)

Background

Key facts

CourtUS District Court, Southern District of New York
CaseUnited States v. Maduro, 11-cr-00205
Charges against MaduroNarco-terrorism conspiracy, torture conspiracy, cocaine importation conspiracy, machine gun and destructive device offences
PleaNot guilty, entered January 5, 2026, and again to the superseding indictment on October 15, 2026
JudgeAnalisa Torres, after Judge Alvin Hellerstein died on October 28, 2026
Trial dateJune 14, 2027 (set before the reassignment)
US reward before captureUp to $50 million (set August 7, 2025)

Related timelines

Sources

39 records, ranked by type
  1. 1Government document31 Jul 2017
    Treasury Sanctions the President of Venezuela
    US Department of the Treasury · home.treasury.gov
  2. 2Official record29 Aug 2017
    Executive Order 13808: Imposing Additional Sanctions With Respect to the Situation in Venezuela
    Federal Register · federalregister.gov
  3. 3Official record24 May 2018
    Executive Order 13835: Prohibiting Certain Additional Transactions With Respect to Venezuela
    Federal Register · federalregister.gov
  4. 4News report22 May 2018
    Nicolas Maduro expels US envoy amid new sanctions
    Al Jazeera · aljazeera.com
  5. 5Subject's own statement23 Jan 2019
    Statement from President Donald J. Trump Recognizing Venezuelan National Assembly President Juan Guaido as the Interim President of Venezuela
    The White House (archived) · trumpwhitehouse.archives.gov
  6. 6News report23 Jan 2019
    Venezuela's Maduro cuts off U.S. relations after Trump backs opposition leader Juan Guaidó
    NBC News · nbcnews.com
  7. 7Official record30 Jan 2019
    Executive Order 13857: Taking Additional Steps To Address the National Emergency With Respect to Venezuela
    Federal Register · federalregister.gov
  8. 8Government document28 Jan 2019
    Treasury Sanctions Venezuela's State-Owned Oil Company Petroleos de Venezuela, S.A.
    US Department of the Treasury · home.treasury.gov
  9. 9Official record7 Aug 2019
    Executive Order 13884: Blocking Property of the Government of Venezuela
    Federal Register · federalregister.gov
  10. 10Government document
    Nicolás Maduro Moros (Narcotics Rewards Program)
    US Department of State · state.gov
  11. 11News report31 Jan 2025
    Venezuela frees 6 Americans after meeting between Maduro, Trump envoy
    Voice of America (Associated Press) · voanews.com
  12. 12Official record20 Mar 2025
    Proclamation 10903: Invocation of the Alien Enemies Act Regarding the Invasion of the United States by Tren de Aragua
    Federal Register · federalregister.gov
  13. 13Official record27 Mar 2025
    Executive Order 14245: Imposing Tariffs on Countries Importing Venezuelan Oil
    Federal Register · federalregister.gov
  14. 14Official record4 Aug 2025
    Notice of OFAC Sanctions Actions (Cartel de los Soles)
    Federal Register · federalregister.gov
  15. 15News report2 Sep 2025
    Trump says US has carried out strike against drug-carrying vessel that departed from Venezuela
    WLRN (Associated Press) · wlrn.org
  16. 16News report2 Sep 2025
    U.S. military kills 11 in strike on alleged drug boat leaving Venezuela, Trump says
    CBC News (Associated Press) · cbc.ca
  17. 17Official record24 Nov 2025
    Foreign Terrorist Organization Designation of Cartel de los Soles
    Federal Register · federalregister.gov
  18. 18News report30 Nov 2025
    Trump confirms conversation with Venezuela's Maduro
    KSL (Reuters) · ksl.com
  19. 19News report30 Nov 2025
    Trump says Venezuela airspace 'closed in its entirety'
    RTHK (AFP) · news.rthk.hk
  20. 20News report16 Dec 2025
    Trump orders blockade of 'sanctioned oil tankers' into Venezuela, ramping up pressure on Maduro
    Local 10 (Associated Press) · local10.com
  21. 21News report17 Dec 2025
    Trump orders blockade of Venezuela's sanctioned oil tankers
    Dhaka Tribune · dhakatribune.com
  22. 22News report5 Jan 2026
    Maduro pleads not guilty in New York court
    RTE (Reuters) · rte.ie
  23. 23News report5 Jan 2026
    Handcuffed and limping, Venezuela's ousted leader Maduro faces US court for first time
    Gulf News (AFP, AP) · gulfnews.com
  24. 24Official record15 Jan 2026
    Executive Order 14373: Safeguarding Venezuelan Oil Revenue for the Good of the American and Venezuelan People
    Federal Register · federalregister.gov
  25. 25Official record17 Apr 2026
    Rescission of the Suspension of All Direct Commercial Passenger and Cargo Flights Between the United States and Venezuela
    Federal Register (Department of Homeland Security) · federalregister.gov
  26. 26News report26 Mar 2026
    Judge refuses to dismiss Maduro case but questions blocking of funds for his defense
    MercoPress · en.mercopress.com
  27. 27Official record25 Feb 2026
    Executive Order 14389: Ending Certain Tariff Actions
    Federal Register · federalregister.gov
  28. 28News report23 Jul 2026
    New York judge sets June 2027 for the start of Maduro and Cilia Flores's trial
    MercoPress · en.mercopress.com
  29. 29News report3 Sep 2026
    Ex-Venezuelan President Nicolás Maduro and wife seek to end drug charges case on immunity grounds
    OPB (Associated Press) · opb.org
  30. 30News report
    Former Venezuelan president Maduro and wife move to dismiss drug trafficking indictment on sovereign immunity grounds
    JURIST · jurist.org
  31. 31News report4 Oct 2026
    US prosecutors say Maduro has no immunity from narco-terrorism case
    The Edge Malaysia · theedgemalaysia.com
  32. 32News report4 Jan 2026
    What the Noriega case can tell us about Maduro's upcoming legal battle
    ABC17 News (CNN) · abc17news.com
  33. 33Government document26 Mar 2020
    Nicolás Maduro Moros and 14 Current and Former Venezuelan Officials Charged with Narco-Terrorism, Corruption, Drug Trafficking and Other Criminal Charges
    US Department of Justice · justice.gov
  34. 34Government document8 Oct 2026
    Nicolás Maduro Moros and Cilia Adela Flores de Maduro Charged with Torture
    US Department of Justice · justice.gov
  35. 35News report15 Oct 2026
    Venezuela's Maduro pleads not guilty to US conspiracy to torture charges
    Al Jazeera · aljazeera.com
  36. 36News report15 Oct 2026
    Venezuela's Nicolas Maduro pleads not guilty to torture
    WDBO (Associated Press) · wdbo.com
  37. 37News report15 Oct 2026
    Ex-Venezuelan President Nicolás Maduro says new torture allegations are 'false'
    ABC30 (Associated Press) · abc30.com
  38. 38News report28 Oct 2026
    Alvin K. Hellerstein, a federal judge who handled Trump, Maduro and 9/11 cases, dies at 92
    WFTV (Associated Press) · wftv.com
  39. 39News report28 Oct 2026
    Alvin K. Hellerstein, a federal judge who handled Trump, Maduro and 9/11 cases, dies at 92
    WPTV (Associated Press) · wptv.com

Last updated 31 October 2026. Spotted an error? See corrections. Every event links to the record it comes from. Allegations are attributed to whoever made them.