Friday Round Up! 10/17/25

Why the Trump administration is using the CIA to do an end-run around Congress.

I know the big news this week is the indictment which dropped on Thursday against former national security adviser John Bolton, but since Renato and I will likely dissect that in next week’s pod, I want to turn instead to a topic I wrote about earlier this week: The drone strikes being carried out in the Caribbean.

As I wrote in my piece, the legal justification for these strikes rests on highly dubious grounds — unless I am missing something, they are actually outright illegal under both domestic and international law. Indeed, also on Thursday, the head of the U.S. military’s Southern Command, Adm. Alvin Hosley, is stepping down, reportedly after expressing concerns about the military strikes on the alleged drug boats (which are now up to five). This came one day after the New York Times reported that the Trump administration has authorized CIA covert actions against Venezuela.

This is bad. (As in, worse than what the military was doing before.)

To explain, let’s go back to the beginning. The CIA, as you probably know, is our primary peacetime intelligence gathering agency. “Intelligence gathering” is the operative term here — about 85% of the agency’s work involves using human, and to a lesser extent, technical, sources to gather information that can be analyzed and used by “consumers,” i.e., U.S. policymakers, to inform their political, diplomatic, and military decisions.

A small part of its mission, though, involves “covert action,” which is a term used to describe secret operations used to affect the political, economic, or military conditions in a target country. The legal basis for covert actions come from a provision of the National Security Act of 1947 known as “the fifth function” (so named because of its place on the list of things that the CIA was authorized to do in the original act), which says that in addition to gathering intelligence and doing a few other things, the CIA can perform “other such functions as the president may direct.” The reason it’s not spelled out, and why it’s “covert,” is because the U.S. wants its hand in these operations to remain concealed — the idea is to have plausible deniability.

Beginning with the Truman administration, the “fifth function” was interpreted to allow the CIA to do a bunch of crazy #@^&$, many of which are likely familiar with from our history. (See, e.g., Italy, Iran, Cuba, and Chile, to name a few countries where the CIA conducted covert ops.) When I teach covert action in my National Security Law class, I teach the “covert action ladder,” which is the theoretical model of the kinds of things undertaken in this capacity (and how plausible deniability becomes harder to maintain the more violent the operation):

(A good history of CIA covert ops, if you are interested, is Tim Weiner’s Legacy of Ashes — Weiner was also a speaker for my Substack class and has a new book out, The Mission, which looks at covert ops since 9/11).

In the wake of Watergate, the CIA released a 700-page report to Congress which detailed its covert ops over the previous decades. The revelations led to increased oversight and some prohibitions, such as the one on assassinations which was included in Executive Order 12,333 by President Reagan (which also explicitly authorized covert actions approved by the president).

But the real guardrails on covert action didn’t come until after Iran-Contra, when it became clear that President Reagan’s NSC was evading appropriations prohibitions on providing arms to the Contras in Nicaragua. Without going down the whole rabbit hole of the scandal, the upshot was that Congress increased oversight of covert actions through the Intelligence Oversight Act of 1991, which prohibited the use of appropriated funds for covert actions unless the following requirements were met:

1. A contemporaneous written finding by the President that it is “necessary to support an identifiable foreign policy objective” and

2. Specifies all the agencies involved and

3. Reported to the House and Senate Intelligence Committees “as soon as possible” or, in “extraordinary circumstances,” it only needs to be reported to the chair and ranking members of these committees “in a timely fashion”

Importantly, covert actions can’t be used to influence U.S. political processes (i.e., no covert propaganda against Americans) and cannot violate the laws of the U.S. or the Constitution. More on that in a minute.

All of this provides some background for why, just a couple of weeks ago, Michael Ellis, the Deputy Director of the CIA, mysteriously (and somewhat unethically) installed himself as the general counsel of the CIA. Ellis’ name might sound familiar because he is the “Where’s Waldo” of the Trump administration, often surfacing when something sketchy has happened (I explained more in this Round Up). I surmised at the time that Ellis was replacing the career lawyer in the agency in order to ensure that the intelligence to support the required presidential finding for covert actions got though.

It looks like I was right, and here’s why this matters: Military actions implicate congressional war powers and could be subject to limitations under the War Powers Act. At the very least, introducing the armed forces into “hostilities” — which is the word the Trump administration itself has used to describe the strikes — triggers ongoing reporting requirements and the so-called “60-day clock” within which congressional approval is required. Senate Democrats have already tried to use congressional war powers to stop the strikes, with Republicans Rand Paul and Lisa Murkowski joining them. (The measure failed, 48-51, with Ted Cruz missing…of course.)

Using the CIA essentially allows the Trump administration to end-run these requirements. Although the Intelligence Authorization Act of 1991 prohibits the CIA from using its covert action authority to conduct “traditional military activities,” it’s not clear what that means and frankly, any distinction between covert action and military action was blurred by the CIA’s conducting of drone strikes, along with the military, in the war on terror. So now the chickens are coming home to roost from the failure to cabin or put any meaningful oversight or guardrails on that.

Apart from evading the War Powers Resolution and congressional oversight, using the CIA also gives the administration a more pliable foot soldiers, as it were. CIA officers aren’t constrained by — to use Defense Secretary' Hegseth’s words — “stupid rules of engagement” or the Geneva Conventions or a clear professional obligation not to follow unlawful orders. In a prescient Washington Post op-ed written after the Supreme Court’s immunity ruling in 2024, a former NSA lawyer and former CIA clandestine officer wrote that the danger of putting a president above the law was not him giving illegal orders to the military, but rather turning to the CIA to accomplish its objectives:

Because of the inherent difficulties involved in ordering the military, with its separate judicial system under the Uniform Code of Military Justice, to engage in illegal activities, it is far more likely that a president would turn to the CIA or engage with private paramilitary groups to carry out any questionable ‘official acts.’ The CIA has the authority to provide the kind of clandestine support necessary to fund a private paramilitary organization (e.g., offshore bank accounts, corporate structures) for both domestic and foreign operations. With approval from the attorney general, such operations could fall under the National Security Act as ‘other functions and duties related to intelligence affecting the national security as the President . . . may direct,’ which would place them outside the existing laws dealing with covert action.

On that last point, it’s worth highlighting that the National Security Act of 1947 states that the CIA may not engage in “internal security functions” inside of the geographical United States. However, Executive Order 12,333 (the same one signed by Reagan that prohibits assassinations) allows for such activity with the attorney general’s permission. You think Pam Bondi is going to say no?

The big tell in this whole CIA thing is…the administration isn’t denying it! Remember the part about “plausible deniability”? The ENTIRE POINT of using the CIA to conduct covert operations is so that as the President, you can say “it’s not us.” Obviously, by openly providing reporters this information, plausible deniability is not the point — in fact, the administration seems eager for it to be known. That leaves trying to end-run Congress as the only reason to use this route.

One heartening sign is that Congress is not giving up — well, at least not the Democrats, and Senator Rand Paul. They are teaming up to pass a resolution to prevent Trump from using the CIA for military strikes without a congressional declaration. Unfortunately, the time to clarify the CIA’s role in military actions was probably a decade and a half ago — let’s hope it’s not too late now.

This week, Renato and I discussed the holes in the Letitia James indictment and the implications of NPSM-7, which purports to designate “domestic terrorist organizations”:

Join me and Renato in Alaska!

It’s Complicated is cruisin’! Come join me and Renato as we explore the stunning beauty of Alaska and discuss how we can work together to protect our democracy! It’s a small ship, and there will be lots of opportunities to talk to us both, plus we will have an opening and closing reception and dedicated democracy discussion tables throughout the cruise. You can find out more at this link, and fill out your info here to have an agent call you with more information. Stay tuned for our next happy hour/info session!

Upcoming events:

• THIS WEEK! Zoom Office Hours, Thursday, October 23, 5 p.m. EDT with special guest Molly Jong-Fast! I am so excited to have Molly join us to discuss the latest. Zoom link will be sent to paid subscribers three hours before the event. Office hours are not recorded.

• The Freedom Academy Book Club with David S. Abraham, author of Elements of Power: Gadgets, Guns, and the Struggle for a Sustainable Future in the Rare Metals Age, Tuesday, October 28, 8 p.m. (sorry for the late timing but David is in Jakarta!) If you’re trying to follow the debate about critical and rare earth minerals (or want to know the difference between the two), you won’t want to miss this talk! Zoom link will be sent to paid subscribers three hours before event. The talk will be recorded and posted for paid subscribers.

• Class Guest Speaker Professor John Witt, author of the forthcoming The Radical Fund: How a Band of Visionaries and a Million Dollars Upended America, Wednesday, November 5, 7 p.m. EST. Our current moment has many parallels to the Gilded Age. The Progressive Era, which followed, generated many grassroots movements and jumpstarted our democracy towards what Scholar Robert Putnam calls an “upswing.” Professor Witt’s book is about one of those movements, which may hold lessons for us today. Please join! Zoom link will be sent to paid subscribers three hours before event. The talk will be recorded and posted for those who cannot make it live.

• NEW! Time/Date TBA (likely late November/early December). Class Guest Speaker David Pepper, author of the Pepperspectives Substack, on Local Affairs and the Habits of Democracy. So excited to have my friend, law school classmate, and colleague David — who has been a previous guest speaker for my Substack class on the role of state politics in facilitating autocracy — come and talk to us about how we can effect change at the local level. Zoom link will be sent to paid subscribers three hours before event. The talk will be recorded and post for those who cannot make it live.

WHAT CAN YOU DO?

I am getting a lot of questions from friends and colleagues asking what they can do in this urgent political moment. I have three potential actions steps you can take now:

1. Pro bono lawyers are on the front lines to stop Trump’s breakdown, takedown, and shakedown of the federal government. You can contribute to this effort on the donation page of State Democracy Defenders Action

2. Get out to the No Kings march today!! Find the one near you here.

3. Self care tip of the week: Phone a(n old) friend. This weekend is my 25th law school reunion and it is so nice to connect with someone who knew you in the Before Times. It’s a great reminder that there was life before this time of chaos and there will (most likely) be life after. Plus, some of the people I am connecting with actually worked in Trump 1.0 and it’s a good meditative practice to be able to try to set that aside for a little while to reminisce about old times and talk about our kids. (Hey, we all need to practice for Thanksgiving, amirite?)

‘Rise like Lions after slumber
In unvanquishable number—
Shake your chains to earth like dew
Which in sleep had fallen on you—
Ye are many—they are few.’

— The Masque of Anarchy by Percy Bysshe Shelley, stanza XXXVIII