Mar 8, 2024 · 38m · american-optimist
Ep 80: Leonard Leo Knows How to Win and How to Save Our Country · Joe Lonsdale
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In this episode of American Optimist, host Joe Lonsdale interviews legal strategist Leonard Leo to discuss strategies for dismantling the administrative state, promoting constitutional Originalism, and cultivating leaders across American civil society.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Joe holds 34.1% of the talking time here. How this is scored →
Joe as informed peer 5.5 Guest teaching 3.0 Guest disagreement 0.3 Joe pushing back 0.3
speaking balance: gold is Joe, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 10:25 Leo dismisses Eighth Amendment remedy
In a very collegial interview, Leo's most direct disagreement occurs when he politely rejects Lonsdale's suggestion that the Eighth Amendment's excessive fines clause could be used by the Supreme Court to strike down politicized state civil judgments.
Hardest push from Joe ▶ 10:25 Lonsdale probes constitutional checks on state court finesLonsdale pushes for a direct legal remedy against what he views as rogue state court judgments targeting political adversaries, questioning whether federal constitutional provisions on excessive fines can intervene.
Biggest teaching moment ▶ 4:14 Leo clarifies original public meaning vs. framer intentLeo provides a crisp pedagogical explanation clarifying that originalism depends on the original public meaning understood by the electorate at ratification, rather than the subjective intent of individual framers like Madison or Hamilton.
Joe holds their own ▶ 23:28 Lonsdale details FTC legal theories and Axon precedentLonsdale displays sharp legal and regulatory knowledge, citing Lina Khan's New Brandeis school, biotech acquisition blocks, and the specific Supreme Court precedent Axon v. FTC.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Joe as informed peer | Guest teaching | Guest disagreement | Joe pushing back | Why |
|---|---|---|---|---|---|---|
| Leonard Leo's Current Work and Philanthropy | 4 | 3 | 0 | 0 | Lonsdale opens by asking about the origins of conservative legal reform and originalism, noting historical figures like Robert Bork. Leo defines originalism as original public meaning rather than subjective framer intent in a collaborative educational tone. | |
| Building Movements & Playbook for Cultivating Talent | 4 | 2 | 0 | 0 | Lonsdale draws parallels between legal talent cultivation and mission-driven venture building. Leo outlines the Federalist Society playbook of establishing clear principles, recruiting core talent, and building transmission belts to shift culture. | |
| Judicial Nominations, Criteria for Good Judges, and Court Weaponization | 5 | 4 | 1 | 1 | Lonsdale references his Wall Street Journal op-ed with Jeb Bush regarding politicized litigation against Donald Trump and Elon Musk, probing whether the Eighth Amendment's excessive fines clause could intervene. Leo gently demurs, noting the clause likely does not apply to that context and reaffirming that personnel is policy. | |
| The Administrative State & Dismantling Chevron Deference | 6 | 3 | 0 | 0 | Lonsdale criticizes the administrative state using historical analogies like the Star Chamber and cites rogue SEC disclosure mandates. Leo details the legal mechanics for dismantling Chevron deference, non-delegation doctrine, and federalism constraints. | |
| Tech Accelerationism, Strategic Litigation, and Talent Pipelines | 6 | 2 | 0 | 0 | Lonsdale articulates the tech sector's effective accelerationist (e/acc) philosophy and asks how donors can deploy capital strategically. Leo maps accelerationist goals to constitutional principles and proposes funding strategic litigation and institutional talent pipelines. | |
| FTC Overreach and Antitrust Abuses | 7 | 3 | 0 | 0 | Lonsdale demonstrates high subject mastery by citing Lina Khan, the New Brandeis school of antitrust, and the Axon v. FTC precedent. Leo expands on the critique by outlining the 'iron triangle' between FTC enforcement, plaintiffs' bar, and progressive state attorneys general. | |
| CFPB Funding Case, EPA Rulings, and Regulator Accountability | 6 | 3 | 0 | 0 | Lonsdale introduces the constitutional defect in CFPB's independent Federal Reserve funding and the West Virginia v. EPA ruling on power plant emissions. Leo details the separation of powers and the congressional power of the purse as essential bulwarks against administrative overreach. | |
| Electorate Accountability, Civic Education, and Civil Society Reform | 6 | 4 | 1 | 1 | Lonsdale asks whether administrative regulators should be easier to fire directly, but Leo reframes the solution around civic education and holding the electorate accountable. Lonsdale extends this with Thomas Jefferson's writings on natural aristocracy and civil society capture. |
Statements from this episode (14)
Lonsdale: Leonard Leo Put Judges in Place to Fight Regulatory State
“He's put the judges in place to go to war against the broken parts of our regulatory state to fix our government.”
Leonard Leo manages Marble Freedom Trust to drive legal and social change
“I now manage a trust called Marble Freedom Trust, so we're trying to really institute a lot of legal and social change through philanthropy.”
Leo: The Warren Court Used the Law as a Political Tool
“The left began to use the law as a really serious driver for social change. And you know, the Warren court played right into that and began to use law as a political tool.”
Leo: Scalia Said Good Judges Need Smarts, Originalism, and Moral Courage
“Oh, I think it's really just three ingredients. One is smarts. And I learned this actually from Justice Scalia, who told me once, you always want a really smart judge, and the reason why you want a really smart judge is because they can't get snookered by the …”
Lonsdale: Court rulings against Trump and Musk are weaponized persecution
“And we talked about the use of the state's judicial systems to persecute political enemies both of course with Donald Trump and Elon Musk recently with rulings that, you know, even though I looked into them in a lot of detail, they both seem to be BS and to be…”
Leo: No rules can constrain a rogue judge, only appointment vetting
“Look, personnel is policy. You just have to pick the right judges. There's no rule that you can put in place That's going to contain or constrain a rogue.”
Leo: The Supreme Court is seriously considering overturning Chevron deference
“And so now we're, what we're faced with is a world where the Supreme Court's very seriously considering getting rid of this doctrine because it's been abused and it's violating the separation of powers.”
Leo: Chevron deference enabled politically motivated judges to expand government
“Frankly, if you ask me, Joe, Chevron was also giving a lot of judges who are more politically motivated the ability to just kind of rubber stamp lawlessness by bureaucrats. And usher in an era of much bigger government.”
Leo: Many constitutional cases will challenge administrative state in 3-5 years
“There are many more of those cases that are going to be brought over the next three to five years.”
Leo: An 'Unholy Alliance' of FTC, Lawyers, and AGs Targets Innovators
“There's this unholy alliance between the FTC enforcement arm and plaintiff's lawyers and leftist state attorneys general. You know, they all feed off of each other and they create this iron triangle of authority and risk, right? Because if you're an innovator,…”
Leo: Beating Back Chevron Doctrine Will Increasingly Restrain the FTC
“I think if we continue to be successful with beating back the Chevron doctrine, And if we continue to be successful in enforcing rules that require Congress to be clearer about what standards agencies need to operate under, yes, I think you can click the wings…”
Leo: CFPB is probably the worst federal agency in US history
“The CFPB, I think is probably the worst federal agency we've ever seen. It violates every single principle of the separation of powers and checks and balances. And this one in particular, not only violates all of that, but it violates the spending power of Con…”
Leo: Entertainment Insiders Seek to Form Alternative Pro-Free-Market Media Ventures
“And I'll tell you, Joe, there are a lot of people in the entertainment world who really understand limited government and free society. And they're not happy with the entertainment world, and they're looking for opportunities to band together and to be a part …”