Maduro’s back in the headlines as Venezuela’s long‑time leader faces renewed international scrutiny and internal pressure—40+ years in politics, ex bus driver turned president.
Anthropic has raised $65 billion in a funding round led by Altimeter Capital, Greenoaks, Dragoneer and Sequoia, valuing the company near $965 billion post‑money and placing it ahead of OpenAI in private valuations. The cash will fund enterprise expansion of Claude, new model development and hiring as Anthropic readies for potential IPOs and broader commercial growth.
On March 14, 2026, the US embassy in Caracas ceremonially raised the American flag, marking the resumption of diplomatic activities seven years after the flag was lowered. This follows the US capture of former President Maduro and the installation of interim President Delcy Rodríguez, with ongoing negotiations focused on Venezuela's oil and mineral resources.
Cuba experienced a nationwide blackout on March 13, with ongoing outages affecting millions. The government attributes the crisis to an aging grid and US sanctions, with recent disruptions linked to halted oil shipments from Venezuela and US policies. Power remains unstable, impacting healthcare and daily life.
The USS Gerald R. Ford, deployed for nine months, arrived at Souda Bay in Crete for maintenance after supporting operations in the Red Sea and Middle East. The ship experienced a fire and crew issues but remains fully mission capable, according to US military sources.
In early April 2026, Russia delivered two oil shipments to Cuba, breaking a US-imposed oil blockade that began in January after the US captured Venezuela's president. The first Russian tanker docked at Matanzas port carrying about 730,000 barrels of crude oil, providing temporary relief to Cuba's energy crisis. The US allowed the deliveries for humanitarian reasons despite ongoing sanctions and threats.
Cuba announced the release of prisoners, including foreigners and Cubans, as a humanitarian gesture for Holy Week. The government did not specify the timing, conditions, or crimes involved. The move follows US pressure and previous releases linked to diplomatic talks and regional politics.
The US has continued its campaign against vessels it identifies as drug-trafficking boats in the Caribbean and Eastern Pacific. Officials say several vessels have been destroyed with fatalities reported, though no public evidence has been released linking the targets to drug cargo. The White House asserts the actions are lawful and part of an armed conflict with cartels; critics call the strikes illegal and indiscriminate.
The US Navy is conducting a review of Ford-class aircraft carriers, including the USS Gerald R. Ford, amid ongoing deployment challenges. The carrier has been at sea for over 300 days, participating in key military operations, but has faced maintenance issues and a fire. The review aims to assess costs and system effectiveness, with decisions on future carriers pending.
The US military has boarded and seized two Iranian tankers, the Tifani and Majestic X, in ongoing efforts to disrupt Iran's maritime support networks. The operations are part of a broader maritime enforcement campaign following a week-long blockade outside the Strait of Hormuz. The vessels are now in US custody, with the White House deciding their future. The US has also turned back dozens of Iranian ships attempting to enter or exit ports since the blockade began. These actions occur amid tense negotiations between Iran and the US, with Iran condemning the seizures as piracy. The US aims to prevent illicit oil transfers and weaken Iran's economic support, intensifying regional tensions.
Master Sgt. Gannon Ken Van Dyke has been indicted on charges including unlawful use of confidential information, theft, and fraud after prosecutors say he placed bets on Maduro-related events on Polymarket, profiting more than $400,000 during Operation Absolute Resolve. The indictment links the trading to classified information and to efforts to conceal proceeds.
Direct commercial flights between the United States and Venezuela have resumed for the first time since 2019. Envoy Air flight AA3599 has landed in Caracas after departing Miami; American/Envoy will add a second daily Miami–Caracas service on May 21. The return of service follows renewed diplomatic ties and recent US actions in Venezuela.
Gannon Van Dyke, a 38-year-old Army master sergeant at Fort Bragg, has been charged with using confidential government information for personal gain and other offenses linked to a $33,000 series of bets on the Maduro raid, which netted about $409,000 on Polymarket. He has been released on bail with travel restrictions and faces further court dates.
The Essequibo region pin worn by Venezuela’s Rodríguez has intensified tensions with Guyana, drawing warnings from Caricom and highlighting the ongoing ICJ case. The gesture is seen as provoking Venezuela’s territorial claim, while Caribbean leaders discuss energy and trade ties amid regional friction.
State budget talks remain unsettled as Gov. Hochul’s push to tie policy reforms to the budget has drawn criticism from Assembly Speaker Heastie and others, signaling a tense, ongoing fight over climate, immigration and fiscal priorities ahead of session end.
The International Court of Justice is holding hearings over the Essequibo region, a border area disputed by Guyana and Venezuela. The 1899 arbitration largely favored Guyana, while Venezuela argues the 1966 Geneva agreement nullifies that ruling. Venezuela’s acting president is attending proceedings; a final judgment is expected months away.
The Trump administration has escalated its campaign of destroying alleged drug-trafficking vessels in Latin American waters. In the latest attacks, U.S. Southern Command has targeted vessels along known smuggling routes, with protests over the lack of publicly available evidence that these boats carried drugs. The operations come as the U.S. has expanded its regional military presence and ahead of a January raid linked to Venezuela’s Nicolás Maduro.
The Trump administration has escalated a counterterrorism strategy targeting drug cartels in Latin America, with reports of deadly strikes on vessels in Caribbean and eastern Pacific waters. Multiple outlets note a lack of public evidence that the vessels carried drugs, while cross-border tensions intensify as regional leaders are urged to act.
Interim President Delcy Rodríguez has defended Venezuela’s sovereignty at The Hague while new U.S. commentary from Donald Trump has reignited talk of making Venezuela the 51st state. Venezuelan officials say Essequibo negotiations continue, and regional tensions are rising as OPEC-style energy interests intertwine with international diplomacy.
The Times has found that hundreds used prediction markets to place bets on geopolitical events, some with ties to insiders; Israel has attacked Iran, earning profits for some bettors. The activity raises questions about insider trading and the role of crowd-sourced forecasts in high-stakes conflicts.
Federal prosecutors in Miami have prepared to unseal an indictment against 94‑year‑old Raúl Castro over the 1996 shootdown of Brothers to the Rescue planes, officials have told reporters. The announcement is scheduled to coincide with a Miami ceremony honouring victims and would need grand‑jury approval. The move has come as U.S.–Cuba tensions are intensifying.
The Nimitz Carrier Strike Group has arrived in the Caribbean, with the USS Nimitz and its air wing conducting exercises and integrating with regional navies. The move is framed as a show of force alongside regional operations, amid ongoing political tensions after Raul Castro’s indictment. The deployment follows a history of prolonged carrier deployments and regional deployments.
Alex Saab has been deported to the United States and is facing a money-laundering charge connected to a long-running bribery scheme tied to Maduro-era contracts. The new Venezuelan leadership is pursuing insider figures, with ongoing investigations touching CLAP program and oil deals.
Cuban president Miguel Díaz‑Canel has said Cuba "poses no threat" after US reports — citing classified intelligence — that Havana has obtained more than 300 military drones from Russia and Iran and discussed strikes on US assets including Guantánamo Bay. Cuba has denied the claims and warned a US attack would "trigger a bloodbath."
U.S. prosecutors have indicted Raul Castro, Cuba’s former defense minister, on counts tied to the 1996 shootdown of two exile planes. Castro has been a central figure in Cuba’s military and politics for decades. The case intensifies U.S.–Cuba tensions as Cuban authorities condemn the charges and rally in support of their government.
Spain's National Court has widened its probe into the 2021 €53m Plus Ultra bailout and has searched former prime minister José Luis Rodríguez Zapatero's Madrid office. Zapatero has been summoned to testify on June 2 and has denied receiving payments as investigators examine alleged kickbacks and improper lobbying tied to the airline's rescue.
The U.S. Justice Department has charged former Cuban leader Raúl Castro in connection with the 1996 shooting down of two Brothers to the Rescue planes. The indictment alleges he authorized deadly force after the exile group dropped leaflets over Havana, killing four U.S. nationals. The case adds to rising tensions between the U.S. and Cuba amid ongoing economic hardship on the island.
The Justice Department has charged Raul Castro over the 1996 downing of two civilian planes, amid a broader U.S. effort to pressure Havana. President Trump’s team is pursuing regime change, tying sanctions and diplomatic pushes to hopes of reshaping Cuba’s leadership. Rubio and U.S. officials frame the move as urgent relief for a Cuban populace starved of electricity and fuel.
The U.S. Justice Department has unsealed a federal indictment against Raúl Castro and five others, alleging conspiracy to kill U.S. nationals, murder, and destruction of aircraft in the 1996 downing of two Brothers to the Rescue planes. The charges mark a bold escalation in U.S. attempts to pressure Cuba’s government; officials in Havana deny the allegations.
Since mid‑May the U.S. has unsealed an indictment charging former Cuban leader Raúl Castro over the 1996 downing of civilian planes, tightened sanctions including broad measures against GAESA, deployed the USS Nimitz to the Caribbean, and imposed an oil blockade that has triggered blackouts and economic strain in Cuba.
A 35-year-old detainee has been released from Rodeo I after nearly 15 months amid espionage accusations linked to Nicolás Maduro’s government. He describes beatings and limited medical care during detention. Authorities plan to release hundreds more detainees, but critics say political prisoners remain.
Two Marine Corps Osprey aircraft have flown over the recently reopened U.S. Embassy in Caracas and landed in the parking lot as part of a drill for medical emergencies or catastrophic events; the exercise follows the embassy’s reopening and ongoing U.S. plans to stabilize Venezuela.
U.S. General Francis Donovan has met Cuban officials, including General Roberto Legra Sotolongo, in Cuba to discuss security at Guantánamo. The talks come amid renewed U.S. pressure on Cuba, including an oil blockade and sanctions, with the base at Guantánamo Bay remaining in U.S. hands. A formal indictment against Raul Castro adds to regional instability.
Federal investigators are examining whether George Santos placed bets on Kalshi about his own attendance at the State of the Union, with the trades flagged by the market and referred to the DOJ and CFTC. Santos has previously been convicted and pardoned, and his current status is under scrutiny as prediction markets face regulatory pressure.