Sep 2, 2025 – The U.S. military conducts a kinetic strike on a suspected drug‑smuggling vessel off Venezuela, killing more than 80 crew members. A follow‑up “double‑tap” strike later that day eliminates two survivors, prompting accusations that Defense Secretary Pete Hegseth ordered a “kill everybody” directive and that the attack may constitute a war crime[1][5].

Nov 23, 2025 – Venezuelan President Nicolás Maduro appears at a Caracas rally and declares he will not accept “peace of slaves or colonies,” signalling open defiance of U.S. pressure after the September boat strikes[5].

Nov 29, 2025 – President Donald Trump posts on Truth Social that Venezuelan airspace is “closed in its entirety” and warns of imminent attacks on drug‑cartel targets, raising the risk of broader military escalation[5].

Nov 30, 2025 – Aboard Air Force One, Trump tells reporters he had no knowledge of a second strike on the September 2 drug boat and pledges an investigation, while Hegseth defends the operation as lawful under U.S. and international law[14]. Senator Adam Schiff warns the administration’s approach could drag the United States into war and calls for congressional intervention[14].

Dec 1, 2025 – Trump convenes a senior‑national‑security meeting in the Oval Office to plan the next phase of pressure on Venezuela; the Pentagon’s “Operation Southern Spear” now fields more than a dozen warships and 15,000 troops in the Caribbean[8]. Senate Minority Leader Chuck Schumer announces he will file a bipartisan resolution to block any U.S. troops in Venezuela[12]. Senator Angus King calls the alleged “no‑survivors” order a “stone‑cold war crime”[6]. Senator Tim Kaine warns that such an order would violate the law of armed conflict[15]. DHS Secretary Kristi Noem recommends a full travel ban on “flooding” countries[7]. U.S. envoy Steve Witkoff and Jared Kushner depart for Moscow for talks with President Vladimir Putin[7]. Trump also endorses Republican Matt Van Epps in a Tennessee special election[7].

Dec 2, 2025 – Trump announces that U.S. strikes inside Venezuela will begin “soon,” expanding the campaign from maritime to land operations[3][4]. He reiterates that he and Hegseth were unaware of any second strike on the September 2 drug boat, a claim echoed by the administration’s spokesperson[3][4]. Hegseth confirms he watched the first strike live but says the follow‑up decision came from a commander, not from him[3]. He later shifts responsibility to Admiral Frank “Mitch” Bradley, defending the commander’s judgment[7]. Special envoy Witkoff and Kushner meet Putin in Moscow; Putin accuses Europe of blocking a U.S. peace plan for Ukraine and warns Russia is ready if Europe fights[4]. Ukrainian President Volodymyr Zelensky describes the diplomatic climate as “challenging yet optimistic”[4].

Dec 3, 2025 – Former Fox News analyst Judge Andrew Napolitano publicly calls for the prosecution of Defense Secretary Hegseth for a war crime, citing the September 2 double‑tap that killed incapacitated survivors[11]. The Venezuelan state newspaper publishes a cartoon ridiculing Trump’s “warship” approach, while President Maduro vows to defend every inch of Venezuelan sovereignty[10]. Hegseth reiterates that the strikes are lawful, calling the incident “fog of war”[10].

Dec 19, 2025 – Senate Republican Marco Rubio states that the Caribbean boat strikes required no congressional approval, framing them as part of a broader pressure campaign that includes seizing an oil tanker, blockading Venezuelan oil shipments, and targeting Maduro’s finances[9]. He says the administration has legal documentation to justify the actions, while Senator Chris Murphy and Representative Mike Massie criticize the moves as war‑hawk profiteering[9].

Jan 3, 2026 – Trump orders a large‑scale strike inside Venezuela and orders the capture of President Nicolás Maduro, presenting the operation as a regime‑change effort that proceeds without congressional authorization[2]. Administration officials initially claim land strikes need congressional approval, then privately admit they lack a legal justification[2]. They cite a 1989 memo by former Attorney General William P. Barr that argues a president has inherent authority to seize foreign nationals, echoing the legal rationale used in the 1989 Panama invasion[2]. Analysts note the operation mirrors the Panama model—focusing on leader removal rather than full‑scale war—and highlight Venezuela’s oil wealth as a geopolitical driver[2].