The Lawfare Podcast — Lawfare Daily: Grand Conspiracy with Molly Roberts

Date: January 20, 2026
Host: Benjamin Wittes (Editor in Chief, Lawfare)
Guest: Molly Roberts (Senior Editor, Lawfare)

Episode Overview

This episode delves into the so-called “grand conspiracy” theory currently facing scrutiny by a grand jury in the Southern District of Florida, presided over by Judge Eileen Cannon. Host Ben Wittes and guest Molly Roberts parse the origins, substance (or lack thereof), and legal mechanics of a sprawling conspiracy narrative, allegedly connecting Donald Trump’s political and legal troubles across years and government agencies. The conversation is at once sober and incredulous, exposing the legal incoherence of the grand conspiracy claims while taking seriously the fact that they are under active federal investigation.

Main Discussion Points & Insights

What Is the “Grand Conspiracy”?

• Definition and Origins

  • Roberts jokingly describes it as “really, really, really super extra big” (02:20) and explains it's an unprecedentedly broad, time-spanning alleged plot.
  • The claim encompasses multiple elections, top officials (including Hillary Clinton, Barack Obama, CIA Director John Brennan, DNI James Clapper, FBI Director Jim Comey), and various investigations from Russian collusion to Mar-a-Lago and January 6th.
  • “The grand conspiracy in this case is a plot so large scale that it spans multiple elections, it ties together officials you'd never think would be tied together.” — Molly Roberts, (02:45)

• Allegations

  • At its core, it alleges a unified “deep state” plot, starting with Clinton’s 2016 campaign, to sabotage Trump through manipulated intelligence and subsequent prosecutions.
  • Central to the narrative are “document dumps” including the discredited “Durham Annex,” said to be forged and potentially Russian sourced, purporting to show Obama and officials framing Trump. (06:20–07:20)

• Mar-a-Lago’s Role

  • The Mar-a-Lago classified documents case is used as a device to bring the sprawling theory into the jurisdiction of Florida, specifically under a Trump-friendly judge.
  • “Mar A Lago kind of gets you to Florida, right?” — Ben Wittes, (13:29)

How Did This Turn into a Criminal Investigation?

• Grand Jury Mechanics

  • Despite the theory’s incoherence, a grand jury has been convened in Fort Pierce, FL, with a pattern of forum-shopping to get a receptive Judge (Eileen Cannon).
  • Subpoenas—mostly for classified documents these officials can’t access—have been issued to various former intelligence officials. (12:12; 41:32)

• Protagonists Behind the Scenes

  • Mike Davis, head of the Article 3 Project and close ally of U.S. Attorney Jason Redding Quinones in Florida, is identified as a “shadow prosecutor,” consistently privy to otherwise secret proceedings.
  • Davis is cited as “the animating spirit” behind the investigation, pressing for it publicly and leveraging connections to inject loyalists into key positions. (20:42–22:09)

• Jurisdictional Engineering

  • The podcast explores how Mar-a-Lago was tenuously used to justify venue in Florida. Even that stretch is further strained by moving proceedings from West Palm to Fort Pierce, aiming for Judge Cannon. (13:33–15:23)
  • “Eileen Cannon is the only sitting judge in Fort Pierce. As it turns out, this does not 100% guarantee that she would ultimately be presiding over the case... but she will be doing so every alternating month.” — Molly Roberts, (14:29)

Legal and Factual Incoherence

• Lack of Clear Statutory Offense

  • The only hinted statute is “conspiracy against rights” (paralleling a January 6th charge), but this doesn't logically bind all the implicated acts or people.
  • “They'll have to identify the statute which Mike Davis has hinted is this conspiracy against rights statute... but they have not, to the targets of any of the subpoenas, articulated any particular crime.” — Molly Roberts, (34:05)

• No Evidence of an Actual Agreement

  • Both Wittes and Roberts return to the legal requirements for conspiracy: an actual agreement to break the law. Here, there is no plausible evidence of such.
  • “Is there any... suggestion about when who formed such an agreement?” — Wittes (18:00)
  • “Only in kind of the earliest stages... a lot of this is in the discredited Durham annex.” — Roberts (18:37)

• Practical Obstacles

  • Any real investigation would quickly falter: witnesses can't testify to what never happened, subpoenaed evidence doesn’t exist, and documents cited are discredited or unauthenticated.
  • “I don't know who your witness would be, right?... None of them is going to testify that this was a corrupt process.” — Ben Wittes, (47:01)

The Role of Trump and Loyalists

• Trump’s Perspective

  • Trump’s own role is less tactical than narrative—he tends to collapse all investigations into a single persecutory “hoax,” while lower-tier loyalists tie it into actionable legal theory.
  • “I think Trump is content as long as everyone gets prosecuted... for whatever is most convenient.” — Molly Roberts, (26:18)

• The MAGA Legal Tactic

  • The strategy seems less about actual prosecution than performative grievance; moving cases to friendlier jurisdictions, targeting perceived enemies, and perpetuating the “witch hunt” narrative.
  • Wittes: “One way to expect is like February 1st, you get a slew of motions to quash... another possibility is that it's easier to talk about a grand conspiracy and tweet about it than it is to investigate it.” (40:16)

Courtroom Realities and Prognosis

• Obstacles for Prosecutors

  • Successfully sustaining such a case, even with favorable judicial conditions, remains extremely unlikely: the facts, legal standards, and evidentiary requirements are insurmountable obstacles.
  • “You shouldn't want, if you're these prosecutors, to have to end up in a courtroom explaining this case... I can't really identify an agreement, and I can't really show intent...” — Molly Roberts, (42:54)

• Potential Outcomes

  • Despite the jaw-dropping implausibility, Wittes and Roberts admit that—given recent political-legal history—it’s possible some litigation and noise emerges.
  • “Every time I have predicted that something is gonna peter out cause it's too dumb, somebody ends up getting indicted.” — Ben Wittes, (50:49)
  • Roberts bets some subpoenas will spark procedural litigation, “if only because then it will make me sound slightly less crazy for having explained this whole grand conspiracy.” (50:28)

Notable Quotes and Moments

• On the Circular Nature of the Claims:

  • Wittes: “You sound like a kind of parody of Jim Jordan.” (08:48)
  • Roberts: “Yeah, I feel crazy.” (08:50)

• On the Legal Flimsy-ness:

  • Wittes: “In a conspiracy, there has to be an agreement... is there any suggestion about when, who formed such an agreement?” (18:00)
  • Roberts: “Only in kind of the earliest stages... a lot of this is in the discredited Durham annex.” (18:37)

• On the Reality of Grand Jury Tactics:

  • Wittes: “If a prosecutor just doesn't give a shit... you can, actually... get anybody to indict anybody for anything.” (44:28)
  • Roberts: “If, again, you're nihilistic enough about it, if you're willing to lie, if you're willing to yolo it, I can imagine getting somewhere on some sort of conspiracy related to the interference and collusion investigations, even though, again, there's no there there.” (46:11)

Key Timestamps

• 01:19–03:16 – Introduction and scope of the “grand conspiracy”
• 05:08–08:43 – Allegations and how the theory is constructed from document dumps
• 10:36–14:13 – Mar-a-Lago as jurisdictional bridge; targeting Eileen Cannon's court
• 20:42–22:35 – Mike Davis and the placement of Jason Redding Quinones as U.S. Attorney
• 34:05–36:10 – Likely statutes to be cited and potential judicial responses
• 39:56–41:48 – Subpoenas, obstacles, and possible next steps for the grand jury
• 44:28–47:01 – Conspiracy law as a tool, limits of the evidence, and legal realities
• 50:28–51:32 – Predictions about litigation and lasting impact of the grand conspiracy story

Tone & Style

Wittes and Roberts blend legal expertise and measured incredulity, anchoring every jarring detail in careful skepticism, often with dry or sardonic humor to underscore the implausibility of the whole affair.

Summary for Non-Listeners

• The episode investigates a sprawling, evidence-thin conspiracy theory tying Trump’s adversaries from 2016 onward into a single “grand conspiracy,” now under grand jury review in Florida.
• The narrative is buoyed by a few determined ideologues and legal activists eager to place it before a favorable judge—despite deep skepticism about its legal and factual basis.
• Host and guest are candid about the ludicrousness of the underlying claims, but serious about the legal process and the possibility that such cases, no matter how wild, can produce real-world headaches and consequences.
• The core takeaway: Even the most fantastical theories can acquire legal legs with the right mix of political incentive, judicial engineering, and “YOLO” prosecutorial culture—but their time in court, if it comes, will likely be short and chaotic.