More Ready Than 1962: 18 Months of Prep Against Cuba
The Pentagon has positioned the force. The Treasury has built the legal architecture. A carrier strike group is ninety miles offshore. And last weekend, the influence investigation came home — administrative subpoenas to Hasan Piker, Medea Benjamin, and Code Pink over a March aid convoy. Those are the groups that would push back on a U.S. attack. They’re lawyering up.
The eighteen-month escalation curve runs through two pieces most coverage missed:
— January 14, 2025: Biden, on his way out, tried to delist Cuba as a State Sponsor of Terrorism. The exchange — brokered through the Vatican — was 553 political prisoners freed by Havana. Six days later, on Day One of Trump 2.0, Trump rescinded it.
— June 30, 2025: NSPM-5 reissued. It banned indirect financial transactions with GAESA, the military conglomerate that runs the regime, and broadened the Restricted Entities List from anyone acting “on behalf of” Cuban military to anyone acting “for the benefit of” it. That single phrase widened the legal net every later move bolts onto.
The January 2026 national emergency and oil-supplier tariffs landed as part of the broader U.S. campaign against Maduro — the Venezuela operation cut Cuba’s energy line by design.
The U.S. is more ready for a military operation against Cuba than it was in 1962.
Eric Garland — 30 years of strategic intelligence practice. Game Theory Today is intelligence tradecraft, applied to the open record, for the public.
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Primary sources:
— Politico, “U.S. has the troops in place to attack Cuba,” May 27, 2026
— White House Executive Order 14404, May 1, 2026
— State Department, “U.S. Sanctions Target Cuba’s Military Regime, Elites,” May 7, 2026
— U.S. Treasury OFAC, Cuba designations & general license, May 7, 2026
— USNI News, Nimitz Carrier Strike Group Caribbean arrival, May 20, 2026
— White House, “Addressing Threats to the United States by the Government of Cuba,” January 29, 2026
— Federal Register, “Reissuance of and Amendments to NSPM-5,” August 12, 2025
— White House, NSPM-5, “Strengthening the Policy of the United States Toward Cuba,” June 30, 2025
— White House, rescission of Biden’s January 14 SSOT certification, January 20, 2025
— White House / Biden, Certification of Rescission and NSM-29, January 14, 2025
— Reuters / wire reporting, OFAC subpoenas to Piker, Benjamin, Code Pink, May 23, 2026
