The Federalist Society is surprisingly ambivalent about Trump

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 over any policy created by the executive branch.

So it’s notable that the panel on whether the tariffs are legal fixated on the nondelegation theory, with the two other arguments only coming up as afterthoughts. Rather than pushing a modest legal argument against the one Trump policy many society members appear to find objectionable, the panel largely discussed whether to use the tariffs as a vehicle to advance the broader fight to take power from the executive and reallocate it to a judiciary full of the Federalist Society’s friends and allies.

To be clear, nothing that happened at the Wednesday conference suggests that the Federalist Society is ready to join the #resistance — it’s only been a few months, after all, since the justices most closely affiliated with the society voted as a bloc to allow Trump to use the powers of the presidency to commit crimes. But the event did suggest that there is some daylight between Trump’s vision for the executive branch and that of the sort of people he placed on the bench. And that might present real problems for Trump, especially when his goals do not align with the conservative movement’s traditional free market views.

Kristine Simmons is a former Republican Senate staffer and domestic policy adviser to President George W. Bush, but she opened the Federalist Society’s panel on “DOGE and the Future of the Federal Workforce” with a line that could easily have been uttered by the president of a federal workers’ union: “The American people are truly blessed to have a professional civil service that provides stability in times of transition.”

She said this to introduce a fairly comprehensive critique of how the federal government hires and manages its workforce. Federal employees are “too old,” she said. It is too hard to hire them, too hard to reward good employees, too hard to “deal with poor performers,” and many federal supervisors lack the management skills they need to get the best work out of their workers.

Her primary message to the Federalist Society, however, was that DOGE — the Musk-driven initiative that was supposed to make the government more effective and efficient — has only made these problems with the federal workforce worse.

By targeting probationary employees, new hires who can more easily be terminated before civil service protections kick in, Simmons warned that DOGE severed far too many young workers with “needed technology skills.”

DOGE rescinded job offers for federal employees who agreed to enter into public service in return for a government-funded graduate degree — after the government had already paid for that education. Meanwhile, she asserted, many of the workers choosing to accept DOGE’s efforts to push them out of the federal workforce are “top performers,” an unsurprising outcome since the best employees will have more job prospects elsewhere.

The Trump administration has, at times, stated directly that moving the best workers out of government is one of their goals — shortly after Trump took office, the White House sent an email to federal employees telling them “the way to greater American prosperity is encouraging people to move from lower productivity jobs in the public sector to higher productivity jobs in the private sector.” But many Federalist Society speakers warned that this approach would sabotage conservative policy objectives.

While the executive branch has considerable power to make policy, it typically can only do so after an extraordinary amount of work. To change or repeal a federal regulation, for example, the government normally must solicit input from outside stakeholders, respond to that input, and explain why it decided to shift course. And the courts can scrap major policy initiatives over bureaucratic errors.

In the first Trump administration, for example, the Supreme Court struck down Trump’s attempt to end the Deferred Action for Childhood Arrivals program, which allows hundreds of thousands of immigrants to live and work in the United States, over a paperwork error.

If it’s willing to do the hard work of policy analysis and exposition, a presidential administration can achieve a great deal of change over time, but it can’t do that without a workforce that is ready and able to do this labor. As Bridget Dooling, a former White House lawyer and law professor, told the society, “laying off, demoralizing, and immiserating the civil servants who work in the federal agencies reduces the capacity to write these reasoned explanations.” And that means that current policy remains locked in place.

Trump’s efforts to “drain the swamp” by eliminating federal employees who may not share the administration’s policy goals risks doing more to undermine those goals than simply leaving civil servants, even those who are left-leaning views, in place. A civil servant might drag their feet if ordered to help repeal a federal regulation, but the least productive government workers are the ones who no longer have their jobs at all.

Meanwhile, several speakers described a mismanaged, directionless workforce. Pierce relayed a message from his daughter, a civil servant: “Nobody’s doing nothing because we can’t figure out what the hell we’re supposed to do.” In the second Trump administration, federal workers “don’t know who is still an employee,” they “don’t know what the mission is,” and, in the case of Pierce’s daughter, “she’s on her fourth boss in three months.”

Pro-DOGE voices were present at the conference, though they faced sharp critique. Rather than attempting to remake the civil service through executive action, the critiques ran, Trump would be wise to attempt to work with Congress to make lasting changes to the administrative state.

So, while the Federalist Society’s voices appeared very sympathetic to the broader projects of weakening civil service protections and redirecting government workers toward conservative movement goals, they described an administration that was ill-suited to this task. DOGE, they warned, is firing or disabling the very workers who are needed to shift policy. And, if Trump won’t work with Congress, any marginal organizational or ideological reforms achieved by his White House could evaporate the minute he leaves office. Trump, in other words, should focus more on lasting, effective policymaking and less on performative changes.

Despite these concerns that this administration will be a missed opportunity for conservatives, there’s little reason to doubt that the Federalist Society’s partnership with Trump will continue to bear fruit.

The conference closed, for example, with a keynote speech by Harmeet Dhillon, a longtime Federalist Society member who Trump recently appointed to lead the Justice Department’s Civil Rights Division. Dhillon spoke with pride about her efforts to shift that office away from traditional civil rights work and toward Republican goals such as ending affirmative action and barring transgender women from school-sponsored sports. She also described DOJ as the “biggest law firm in America,” and is undoubtedly correct that the federal government can play a huge role in shifting the law to the right simply because it has so many resources at its disposal.

But the society also seemed to want far more than Dhillon could offer them. Many of its members were clearly keen to seize even more power for themselves and their judges — even if that means severely weakening the Trump presidency.

The one Trump policy that many Federalist Society speakers expressed deep concerns about on the merits is his trade war — Pierce labeled the tariffs “madness” because businesses cannot make investment decisions when “the tariff’s 120 percent today, might be 200 percent tomorrow, might be zero tomorrow.” At a panel focused on the tariffs, two speakers opposed them and only one attempted to defend their legality. Meanwhile Elizabeth Slattery, the panel’s moderator, identified herself as a lawyer with an conservative legal shop that is suing Trump over the tariffs.

But the bulk of this panel’s discussion of the tariffs was an extraordinarily baroque debate between two lawyers about whether the tariffs violate the “nondelegation” doctrine, a long-defunct legal theory that the Supreme Court has only relied upon twice in its history (both times in 1935). The strongest legal arguments against the tariffs — the claim that Trump lacks the statutory authority to implement them, and the claim that it violates the Supreme Court’s recently created “major questions doctrine” — only came up as afterthoughts.

If you’ve followed the politics surrounding separation of powers closely, this focus isn’t surprising. Since the Obama administration, the Federalist Society has touted numerous proposals to weaken the executive branch’s ability to set policy, and to shift power away from the executive and towards the judiciary — the branch that the Federalist Society most firmly controls.

The nondelegation doctrine claims that judges have sweeping authority to veto executive branch actions that those judges do not like. So, if the tariffs are struck down on nondelegation grounds, that wouldn’t just eliminate a single policy that many Federalist Society members appear to regard as unwise, it would give the society’s judges and justices broad and lasting authority to sabotage future presidential administrations.

While many businesses look at the tariffs and see a president out of control, in other words, the Federalist Society appears to see an opportunity to consolidate its own power at President Trump’s expense -- and at the expense of Trump’s successors.

Similarly, the conference’s lunch panel featured an evenly matched debate about nationwide injunctions, lower court orders which put a federal policy on hold throughout the entire country. The Justice Department, under both the Biden and Trump administrations, staunchly opposes these broad orders, which sometimes permit a single outlier judge to determine national policy for months at a time. And the Supreme Court will hear a case on May 15 that could potentially limit or even eliminate these nationwide orders.

But the panel featured a serious conversation over whether judges should have this power, rather than statements of fealty to Trump’s position. Many audience members also seemed troubled by Trump’s anti-injunction stance — at lunch, I sat between two lawyers who often challenge federal laws in court, and who don’t want to lose the ability to obtain nationwide injunctions against those laws.

There’s no doubt that the Federalist Society’s leading lights are thrilled to have a Republican back in the White House, and the society is likely to spend the next three-and-a-half-years watching Trump turn many of its most MAGA-aligned members into judges. But it was often hard to escape the impression that they would be happier if a more methodical Republican — perhaps a Nikki Haley — occupied the Oval Office. As several speakers argued, the sheer goonishness of Trump’s approach to governance may leave movement conservatives with few lasting victories after he’s no longer president.

Nor is the Society likely to be content as mere coalition partners in a MAGA movement led by figures like Trump. It wants to shape major policy decisions, and perhaps to move in a more market-oriented direction than Trump would prefer, and so is working to consolidate power within the judiciary it dominates.