An Open Letter to Leonard Leo, Concerning the Trump/Musk Lawlessness

Are you okay with this?

Mr. Leonard A. Leo, Esq.
c/o Catholic Information Center
The Investment Building
1501 K St NW, Washington, DC 20005

c/o The Federalist Society
1776 Eye Street, NW
Suite 300
Washington, DC 20006

c/o Marble Freedom Trust
331 W Parrish Lane
Suite 106 315
Centerville, UT 84014

Re: The Eradication of the U.S. Legal System

Dear Mr. Leo:

If you know my name at all, it is from the handful of pieces I’ve written about you, none of which are particularly kind. For that I offer no apologies. I don’t particularly like you. As a Catholic (lapsed) Italian Gen Xer from New Jersey, I especially resent that a Catholic (extremist) Italian Gen Xer from New Jersey has done so much harm to our fellow Americans—women and the LGBT community in particular.

But I’m not here to argue about policy. Indeed, arguing about policy is a luxury that is rapidly being taken away from us, thanks in no small part to you—or, rather, to your chum Clarence Thomas and the five Justices you have wilily placed on Supreme Court: Sam Alito, John Roberts, and the three Trump nominees.

No, I’m writing you today because I have questions—honest, sincere questions—that I’d very much like you to answer. Given your complicity in the country’s free-fall into despotism, I feel like you owe me, and my 340 million fellow citizens, an explanation.

Back around Thanksgiving—after the election but before inauguration—you did an interview with NPR in which you were asked this question: “The President-Elect [Trump] has appointed judges and justices whose view of the law you very much like, but also tends to decide for himself what he thinks is illegal or proper and also wants to punish his critics. Are you concerned about the rule of law in this moment?”

To that timely, prescient question you gave this condescending response: “Well, fortunately, we have a constitutional system that protects against any rash or hasty action by presidents or by other public leaders. The separation of powers helps a lot in that regard and an independent judiciary, and so do the checks and balances between Congress and the executive. So there’s always that risk in any system of government. But it’s the best system of government I think we’ve ever seen in the world in terms of really making it hard for those things to happen.”

We are nine weeks into the second Trump term—what I call the Redux—and Donald has already mooted your answer. In this short time, the President and his Co-President, Elon Musk, have acted so rashly, brazenly, and hastily, with their firehose of executive orders; with DOGE playing life-and-death Jenga with the federal government; and with fatally incompetent if not outright treasonous appointments to key Cabinet positions, that they have broken through the guardrails—overwhelming, by Bannonian design, our fragile system of checks and balances.

Congress has failed to provide an adequate check on power, owing to the preponderance of pusillanimous Republicans in the two chambers; the Senate, with its GOP majority and sclerotic Dem minority leadership, voted to confirm all of Trump’s nominees, however unqualified, however aligned with Putin, however ignorant, however openly vengeful. To its credit, the judiciary has held so far, true—but to what end? The administration is already openly defying court orders, a constitutional crisis that will get worse before (if?) it gets better. Trump, a lifelong criminal, has nothing but contempt for the rule of law. He has called for the impeachment of judges who disagree with him. Lower level judges, suddenly thrust in the spotlight, rightly feel threatened by well-armed stochastic terrorists in MAGA hats. The Chief Justice—your dude—was concerned enough about Trump’s tirades against the judiciary to issue a public statement. Meanwhile, prominent white-shoe law firms have capitulated to Trump’s mafioso-like demands. No doubt you are aware of Paul, Weiss essentially paying protection money to get POTUS off its back.

It gets worse. Although the legacy media is reluctant to say so, Musk has outed himself as a Nazi. I know you have some connection to VP Vance through the Catholic networks, but he is, and has long been, an open fascist. Trump, a yooge fan of Hitler, promised to be a dictator on Day One and is doing his level best to keep that promise.

All of these things are objectively true, and are really taking place. In fact, your old fellow-traveler Ed Whelan has been tweeting his displeasure about the goings-on, leading me to the uncomfortable realization that I sometimes agree with Ed Whelan. Strange bedfellows, indeed.

But I digress. I’m writing today to ask one simple question:

Are you okay with this?

As I have pointed out many times, the only way the United States of America, currently constituted, will ever criminalize abortion, contraception, and homosexuality—as I understand it, the three tenets of your core belief system—is by authoritarian fiat. The American people overwhelmingly want those rights preserved and protected. Are you so laser-focused on these (harmful, hateful, and ignorant) objectives that—like Vance, his whoremaster Peter Thiel, and the “thought leaders” of the Dark Enlightenment—you are willing to shitcan a government of the people, by the people, and for the people?

As you are fond of pointing out, you have spent over four decades working, quite successfully, to make the legal system more to your liking. But you have always done so within the framework of the law. I don’t agree with most of the Roberts Court’s decisions, especially Dobbs and the immunity case.¹ But those rulings were determined by interpretations of existing law. The interpretations were shit, in my opinion, but there was still an earnest (if, in Alito’s case, an insultingly half-ass) attempt to make use of precedent. Your black-robed buddies didn’t just, like, make shit up willy-nilly to please a volatile would-be dictator. Which is what they will spend the rest of their careers doing, if Donald wins the current constitutional crisis—as it appears that he will. Are you good with Trump tossing 249 years of legal precedent out the window? Is the Federalist Society, headquartered as it is on 1776 Eye Street?

I am under the impression that you have reverence for the law. You know, originalism and all that. I’m no constitutional scholar, but if there’s one thing I know for sure, it’s that the Founders damn well didn’t want an American king. Will you sit back and smile as we essentially coronate Donald the Short-Fingered?

Dictators consolidate their power by attacking the press, their political opponents, and judges. This is clearly Trump’s playbook. Once he defies one court order with no repercussions—which has already happened—he will keep doing it, until the entire judicial system becomes a meaningless joke. What your comrades on the Supreme Court don’t seem to grok is that the additional power they gave the President with their idiotic immunity case ruling was effectively created by taking it away from the Justices. Did you really spend your entire adult life laboring to create a Supreme Court full of like-minded Catholic conservatives, only to watch Donald Trump—a godless idiot who called you a “fat fuck”—neuter the Nine?

Maybe you think you can control him? I know you cannot. During the last days of the first Trump term, his Administration was staffed with four kinds of people: 1) crooks, 2) inept buffoons, 3) lunatics, and 4) competent “Opus Dei-adjacent” professionals.² Members of this last group, as you well know, included Pat Cipollone, Eugene Scalia, Bill Barr, and Kellyanne Conway. It was pretty obvious to me that the “Opus Dei wing”—familiar faces in your Catholic Information Center orbit—were trying to exploit Trump’s incompetence to get what they wanted. How’d that turn out? Donald’s MAGA horde besieged the Capitol, like the Doge of Venice’s holy warriors sacking Constantinople in the Fourth Crusade. (I’m going to give you the benefit of the doubt and assume you were not cheering on the insurrectionists, like your old crony and dark money beneficiary Ginni Thomas.) If you could not constrain Trump in 2021, when he was the lamest of lame ducks, what makes you think you can do so now?

Do you think the Barre Seid money will save you? It won’t. The thing about an oligarchy is that no one is safe from the arbitrary caprices of the dictator. Look at what Putin did to Mikhail Khodorkovsky—and Khodorkovsky had a lot more coin than you do. Trump is vengeful and stupid and sadistic, and he holds grudges forever—and he didn’t call you a “fat fuck” because he thrills to your personality. You think he won’t have his lawless lackeys Kash Patel and Pam Bondi investigate your byzantine financials and find some excuse to ship you to El Salvador—without due process, because there will be no more due process by then—once he decides he’s had enough of you?

Finally, think of the children! That sounds flip, but I mean it sincerely. Already children in other countries are starving to death because of DOGE’s cruel cut of funds to USAID programs. You cool with that? As for here in the US of A: Putting aside my extreme abhorrence of your ignorant and harmful stance on abortion—because we are not here to talk policy—you do realize what a Trump/Musk dictatorship means for all the “unborn” you’re protecting, right? Drastic cuts to CPS and SNAP, school lunch programs and welfare. No more vaccines. (Make Diphtheria Great Again!) No more gay couples around to adopt, because you don’t want that, so: orphanages that are underfunded and overflowing, like in some Dickens novel. Those kids who don’t go hungry on our climate change-ravaged planet will grow up to be cannon fodder for the needless wars we’ll be waging with Iran and, I guess, the EU (because of Greenland?). And some of these kids may even be shipped off-world, to toil on a cold red planet and make Mars inhabitable for Elon Musk and his brood. That’s why you’re “saving” the blastocysts? For that brave new world? Is that really what you want? Because make no mistake: that’s what’s going to happen, if we continue along this path.

And so I ask again: Are you okay with this?

If you are, I’d love to know why. Is it because Josemaría Escrivá was down with Franco? Because Pope Pius XII worked with Hitler? Pray tell.

And if you’re not, I beseech you to do something about it. Although most Americans have no idea who you are, we both know that you have had more of an impact on the legal system of this country—and, therefore, its current political climate—than almost any other single individual in my lifetime. You have power, Leonard. Real power. You have resources: billions of dollars at your disposal, via Marble Freedom Trust and your deep-pocketed benefactors like Harlan Crow—not to mention a godly Rolodex. And more than that, you have a preternatural ability to marshal forces, covertly, to achieve desired outcomes. That’s what you do. And that skillset happens to be exactly what the country needs right now. You are one of precious few Americans who could actually stop the looming Trump/Musk dictatorship. Will you try?

If you intend to fight back against tyranny, as both Jesus and George Washington would have done, I am here to help in any way I can. Once the strongmen are removed, we can go back to arguing about policy, law, Catholicism, and how Ruth’s Chris is better than Morton’s.

The ball’s in your—pun very much intended—court.

Thank you for considering these thoughts.

Your fellow New Jerseyan,

Greg Olear

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Photo credit: RDNE Stock Project.

1. Did you enjoy yourself at your celebratory fête after the Dobbs decision dropped, or did certain Washington-Nationals-season-ticket-holding guests get so hammered that they ruined the party?

2. I have always taken great care in not saying that you are a member of Opus Dei. I don’t know if you are and I don’t much care. Let us say you’re “Opus Dei-adjacent,” and leave it at that. (Note: given DOGE’s war on “DEI” and its arbitrary carelessness in enforcing its hateful vendetta, perhaps a name change is indicated?)