The White House has escalated pressure on Cuba through surveillance flights, an energy embargo, and a visit by CIA Director John Ratcliffe, and is considering indicting Raúl Castro, according to The New York Times. The administration is modeling the effort on its Venezuela strategy, which has combined criminal charges against senior officials with economic and intelligence pressure.

The Justice Department instructed federal prosecutors to build criminal drug cases against Mexican government officials using new terrorism statutes, according to The New York Times.

Cuba's top diplomat in the United States, Lianys Torres Rivera, said negotiations with the Trump administration have made "no progress" and that Cuba is holding firm on its red lines amid a threat of U.S. invasion, according to The Hill. Said Torres Rivera: the island is not moving from its stated positions despite the pressure.

Cuba's government is increasingly relying on private businesses that survived years of state suppression to stabilize an economy facing critical shortages of food and fuel, according to Bloomberg Politics. The shift comes as the Trump administration moves to tighten pressure on the island, with private-sector actors now positioned as central to any post-crisis economic transition.

The Justice Department is pushing to indict 94-year-old former Cuban president Raúl Castro for the 1996 downing of two civilian planes that killed four Cuban Americans, according to NBC News. The multi-agency effort is led by the U.S. Attorney's Office for the Southern District of Florida; it is not yet clear whether the case has gone before a grand jury. Said Trump, asked about the investigation: "You talk about a declining country, they are really a nation or a country in decline. So we're going to see."

Erebor Bank, a startup backed by Peter Thiel, has pitched Venezuelan officials on restoring the sanctioned country's access to the US financial system, according to Bloomberg Politics. The move positions a new, politically connected firm in a market that major global banks have continued to avoid under longstanding US sanctions.

Cuba announced it has completely exhausted its diesel and fuel oil reserves, leaving power plants without the energy needed to operate, as scattered civil unrest erupted across the country, according to Bloomberg Politics. The fuel collapse comes amid what Bloomberg describes as a de facto U.S. energy blockade of the island.

Leaked audio messages connecting Brazilian senator Flavio Bolsonaro to the chief executive at the center of a multibillion-dollar bank fraud case are threatening his presidential campaign before it formally launches, according to Bloomberg Politics. Banco Master, the institution at the heart of the scandal, has become a liability for the Brazilian right ahead of what was expected to be a competitive 2026 race.