OK. Challenge accepted.
Here's a ChatGPT analysis of the facts, including judicial decisions designating various of Trump's orders as unlawful. Keep in mind that, from a service member's perspective, a judicially defined unlawful act remains an unlawful act until such time as an Appeal to a higher court is successful (if at all):
ChatGPT (as of 21 November 2025)
Short answer: during his current (second) term, there have been some Trump orders to the military/National Guard that federal courts have already found unlawful, plus others that are under active legal challenge or criticized as violating international law. But there is no single authoritative “master list”, and in several cases appeals are still underway.
Below is a careful breakdown of what’s actually been ruled unlawful so far, and what is still just alleged or contested.
1. Los Angeles: National Guard & Marines (June 2025)
What happened
On 7 June 2025, Trump federalized the California National Guard and sent Guard troops and later Marines to Los Angeles in response to protests against immigration raids, despite the California governor’s objection. (FactCheck.org)
Court rulings
California sued, arguing the deployment violated the Tenth Amendment and exceeded Trump’s authority under Title 10 (the federal statutes governing use of the Guard).
In early September 2025, U.S. District Judge Charles Breyer ruled that Trump’s use of soldiers in Los Angeles was illegal, finding that the conditions required under federal law (rebellion or inability to execute the laws) were not met and ordering the Guard returned to state control. (Brennan Center for Justice)
The 9th Circuit Court of Appeals then temporarily stayed Breyer’s order, allowing the federalization to continue while the appeal proceeds. That means:
At the district court level, the LA deployment has been found unlawful.
But the final word from higher courts is still pending.
So, strictly legally: the order federalizing and using the California National Guard in LA has been held unlawful by one federal court, though that finding is on appeal.
2. Portland, Oregon: Attempted National Guard deployments (Sept–Nov 2025)
What happened
In late September 2025, Trump announced that he had directed the Defense Department to federalize and deploy the Oregon National Guard (and later, Guard units from other states such as California) to Portland to deal with relatively small protests at an ICE facility, characterizing the city as “war-ravaged”. (The Guardian)
An internal presidential memo (June 7, 2025) that also covered these deployments described protests that interfered with ICE operations as a “rebellion” justifying use of troops. (Portland.gov)
Court rulings
Temporary restraining orders (TROs):
In early October 2025, U.S. District Judge Karin Immergut issued TROs blocking Trump from deploying 200 members of the Oregon Guard, then a broader order blocking deployment of any state’s Guard to Oregon after the administration tried to send California troops instead. (ABC News)
Final decision (7 November 2025):
After trial, Judge Immergut issued a 100-page final decision in State of Oregon & City of Portland v. Trump, holding that Trump “did not have a lawful basis to federalize the National Guard” for this purpose and that the planned deployments “exceeded the president’s authority.” She issued a permanent injunction blocking the deployment. (opb)
Appeals
A 9th Circuit panel later ruled that Trump likely has constitutional authority to take command of certain Guard units in some circumstances—but a second restraining order still bars actual deployment in Oregon, and litigation continues. (AP News)
So here, Trump’s orders to federalize and deploy National Guard units to Portland have been held unlawful and permanently enjoined by a federal district court, again subject to ongoing appeals.
3. Other domestic National Guard / troop deployments
Trump’s current-term strategy of using the Guard or other forces domestically (e.g., crime “crackdowns” in Washington, D.C., and proposed deployments to Chicago and elsewhere) has drawn legal challenges and criticism, mainly under:
Posse Comitatus Act (limits federal troops in domestic law enforcement),
Title 10 / Insurrection Act provisions, and
Tenth Amendment (state sovereignty). (Wikipedia)
As of now:
Some deployments (LA, Portland) have been explicitly found unlawful by district courts, as above.
Other deployments or threatened deployments are contested but not yet definitively ruled illegal nationwide; courts and commentators are still wrestling with how far a president can go in using the Guard without state consent.
4. Lethal military action against alleged Venezuelan drug traffickers
This is not National Guard but orders to U.S. military forces, so it’s relevant to your question.
What happened
Reports in August–September 2025 describe a secret presidential decree in which Trump designated some Latin American drug cartels as “terrorist” organizations and authorized the Pentagon to use military force against them. (The Guardian)
Under this policy, U.S. forces killed 11 alleged Venezuelan drug traffickers in international waters, with media and human-rights accounts indicating there was no attempt to interdict or arrest, but rather a direct lethal strike. (The Guardian)
Legal status
Human-rights groups and legal experts argue this amounts to extrajudicial execution and violates international human rights law and the law of armed conflict (because mere designation as “terrorists” does not create a lawful armed-conflict context, and lethal force is only justified against an imminent threat). (The Guardian)
However, as of now, no U.S. court has formally ruled that this specific order or operation was unlawful, and no U.S. service member has (publicly) been prosecuted for carrying it out. The claims of illegality are therefore legal critiques, not judicial findings—at least yet.
5. Things often discussed but not clearly “unlawful orders” (in a narrow legal sense)
A few related points that sometimes get mixed in, but don’t (yet) amount to formally recognized unlawful orders:
Rhetoric about “illegal orders” and the troops:
In November 2025, Trump condemned Democrats who released a video reminding troops they must refuse illegal orders, calling the video “seditious” and saying those lawmakers “deserve death,” though the White House later walked that back. (Reuters)
That episode is about rhetoric and political conflict, not a specific adjudicated unlawful order by Trump himself.
“Shoot them in the legs” remarks:
Reporting from former Defense Secretary Mark Esper recounts Trump (during his first term) asking whether protesters could be shot “in the legs.” That was rejected by officials and never issued as a formal order, and it predates his current tenure. (The Guardian)
Pulling it together
If we stick to a strict legal standard—orders that courts have already found unlawful during Trump’s current term, we mainly have:
The order federalizing and deploying the California National Guard in Los Angeles in June 2025, which a federal district court found violated the Tenth Amendment and exceeded statutory authority (though the ruling has been stayed on appeal). (Brennan Center for Justice)
The attempted federalization and deployment of Oregon (and California) National Guard troops to Portland in September–October 2025, which another federal district court permanently enjoined, holding Trump lacked lawful authority and exceeded his powers. (opb)
Beyond those, there are serious, ongoing legal and human-rights challenges to:
his broader pattern of domestic Guard deployments, and
his secret decree authorizing military killings of alleged traffickers,
but those have not yet produced definitive, final judicial determinations that the underlying orders to military personnel are unlawful.