Few organizations have profited as handsomely off of President Donald Trump’s rise to power as the Federalist Society, a kind of bar association for right-wing lawyers.

“We’re going to have great judges, conservative, all picked by the Federalist Society,” Trump announced during his first campaign for president — and boy did he deliver. Trump spent his first term filling the bench, including three seats on the Supreme Court, with the society’s luminaries.

And yet, at a Federalist Society gathering last Wednesday, which focused on the executive branch of the federal government, both the speakers and attendees seemed far more ambivalent about their president’s second term than one might expect after such a fruitful partnership.

To be sure, few speakers criticized Trump’s policies — except for his tariffs, which several attacked quite directly. But many were quite troubled by what speaker Susan Dudley, an expert on regulatory policy at George Washington University, labeled “the chaos.”

That chaos, the society’s speakers warned, could lead to Trump’s second term becoming a missed opportunity, with a once in a generation chance for deregulation squandered through sheer ineptitude. “They are going to have the same level of success they had in the last administration” with getting rid of long-standing rules and regulations, George Washington University law professor Richard Pierce told the conference, “which is virtually none.”

Implicit in this critique is a belief that the web of procedural barriers, bureaucratic trap doors, and paperwork burdens that prevent any presidential administration from changing too much, too fast will survive the second Trump administration more or less unscathed. Pierce predicted that many of Trump’s deregulatory efforts would simply be struck down in court.

Under current law, he explained, changing regulations “requires really hard work by a whole bunch of people who know what they are doing.” But it’s hard for that work to get done when the bureaucrats who know how to do it have just been fired by Elon Musk’s Department of Government Efficiency.

Indeed, some of the conferences’ speakers didn’t just appear to view DOGE as an obstacle to making lasting progress on conservative deregulatory goals, they also seemed to want to roll back Trump’s power. Some appeared just as eager to strip power from Trump as you might find at a conference of Democratic lawyers, albeit for reasons Democrats would likely find distasteful.

For more than a decade, the Federalist Society has elevated arguments that the judiciary (especially if that judiciary is controlled, as it is currently, by Society allies) should wield powers typically enjoyed by the executive branch. Based on Wednesday’s conference, the society appears just as committed to judicial supremacy as it was when the White House was controlled by Presidents Joe Biden and Barack Obama.

Nowhere was this argument made more forcefully than in discussions over Trump’s tariffs. Broadly speaking, there are three ways that the courts could strike down Trump’s tariffs. They could issue a narrow decision holding that the statute Trump relied on to impose them does not permit him to do so. They could strike them down under the “major questions doctrine,” a new legal framework that the Supreme Court used to sabotage some Biden era policies. Or they could strike them down under the “nondelegation” doctrine, a largely defunct legal concept that would give the judiciary sweeping veto power........

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