Trump’s Split with Leonard Leo Is No Victory for the Rule of Law

The enemy of your enemy is not always your friend.

Note from Mike: This is a guest post by Alex Aronson, co-founder and executive director of Court Accountability. Subscribe to their newsletter, Tilted Scales, and follow Alex on BlueSky. I also weighed in on this subject this weekend on Slate’s Amicus podcast with Dahlia Lithwick. Click here for highlights of my coverage at Weekend Reading of the Roberts Court’s constitutional coup.

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The circus of the Trump-Musk split has already buried a MAGA fracture of arguably equal significance: Trump’s recent broadside against the Federalist Society and Leonard Leo, Trump’s first‑term judicial gatekeeper. Incensed by a Court of International Trade panel—including a judge he appointed—that temporarily blocked his tariff program, Trump ripped Leo, calling him a “sleazebag” and a “bad person” who “probably hates America.” Trump adviser Stephen Miller piled on, accusing the Federalist Society of creating “a broken system,” and vowing not to use the “Federalist Society to make judicial nominations at all going forward.”

After two years of uncomfortable headlines about Leo’s Machiavellian efforts to “weaponize” conservative ideas and remake the nation in his hardline image, Leo couldn’t have asked for a better way to refurbish the persona he’s long projected: that of a principled, mild-mannered thinker who thrives on polite disagreements and healthy constitutional debate. Like the disarming “umpire” he installed as Chief Justice, Leo has cultivated this image with remarkable success, beginning with his introduction to mainstream audiences in Jeffrey Toobin’s glossy 2017 New Yorker profile (which reportedly sits framed in Leo’s office).

Following Trump’s outburst, anti‑Trump voices across the ideological spectrum have fallen back on this flattering narrative about Leo, casting Trump’s feud with the Federalist Society as the latest assault on the rule of law. In The New York Times, columnist David French lauded the Federalist Society as “stubbornly independent.” Cherry‑picking cases to portray the Society’s justices as hostile to Trump’s agenda, French argued that “when there is a conflict between conservative legal principles and Trump’s demands, conservative judges almost always adhere to their principles.” Even liberals, like Cornell Law professor Michael Dorf, have urged progressives to “make common cause with Federalist Society members, leaders, and fellow travelers who, while embracing a very different vision of law and justice than we liberals and progressives embrace, nonetheless believe in law.”

But after decades of precedent‑busting judicial activism, to what “principles” can Leo or his judges truthfully be said to have adhered? Much more than any consistent commitment to jurisprudential principle, the prevailing theme of the Roberts era has been power entrenchment and ideological advance. Like Trump, Leo’s judges believe in “law” only insofar as it means what they say it means. As Chief Justice John Roberts bluntly remarked in 2009, “if [the people] don’t like what we are doing, it’s more or less just too bad.”

From their marble perch on First Street, Leo’s Federalist Society justices—several now tainted by unprecedented corruption scandals, with Leo at the center—have fundamentally reordered our constitutional system, rigging the game for their billionaire patrons and Republican political allies, Trump emphatically included.

In a series of party-line decisions, the Roberts Court burst open the corporate floodgates in Citizens United, gutted the Voting Rights Act in Shelby County, and refused to police partisan gerrymanders. The result: unprecedented influence by billionaires like Elon Musk, while Republican legislatures have revived Jim Crow‑era voter‑suppression tactics and seized an iron grip over half the state governments.

Last summer, Leo’s bloc on the Roberts Court continued to set the stage for Trump’s rise as a populist strongman, including intervening to shield Trump from accountability for his attempt to overturn the 2020 election. Its sweeping expansion of executive power has now emboldened Trump to act with unprecedented lawlessness and impunity, such as was on display this past weekend when he purported to federalize the National Guard to quell mostly peaceful protests in Los Angeles.

While the Trump-Musk feud was dominating headlines late last week, Roberts & Co. closed out the week by quietly handing over Americans’ personal Social Security data over to DOGE by staying a lower court ruling that had blocked the data grab. (One can only guess which of Musk or Trump will get our sensitive data in their divorce, but “both” is a good bet.)

So even as Trump lashes out over conservative challenges to his market‑destabilizing tariffs—policies that threaten Leo’s industrialist donors—the broader record hardly depicts an apolitical Federalist Society judiciary independent from Trump. What emerges instead is a Roberts Court tightly aligned with the structural and ideological aims of Trump’s “post‑Constitutional” Project 2025 agenda. This should come as little surprise seeing as Leo’s dark money has funded some two-thirds of the organizations behind the Heritage Foundation’s Trump 2.0 blueprint.

Viewed through this lens, Project 2025 has been underway in Leo’s courts for years. Under the threadbare banner of “originalism,” partisan Roberts Court majorities have dismantled landmark protections forged through democratic struggle: labor rights, consumer safeguards, environmental regulations, civil‑rights guarantees, and bipartisan gun‑safety laws. With each stroke, the Court has aggrandized its power at Congress’s—and the people’s—expense.

Leo’s judicial culture war agenda has marched just as aggressively, and just as much in lockstep with MAGA’s. After Dobbs toppled Roe v. Wade, red‑state lawmakers sprinted to impose near‑total abortion bans. Likewise, the Roberts Court’s Students for Fair Admissions decision not only outlawed affirmative action in higher education but has served as a springboard for Trump’s assault on diversity, equity, and inclusion programs across the board. The Roberts Court has steadily bulldozed the wall between church and state—green‑lighting open prayer at public‑school football games, forcing taxpayers to subsidize religious schools, and more—all in service of the white‑Christian‑nationalist base that anchors Trump’s coalition. And none of this appears to be slowing.

Facing Trump’s increasingly undeniable fascist designs, the impulse to forge cross‑ideological alliances to defend what remains of the rule of law is understandable—indeed, essential. But the enemy of your enemy is not always your friend. As Virgil warned, beware of Greeks bearing gifts. Acceding to Leo’s version of “rule of law” — or, more accurately, “rule by law” — is accepting the wooden horse.