Some of the most prominent minds behind the conservative legal movement are fighting a Republican president and his administration in court and it’s putting these elite attorneys, many champions of the Right for their past efforts to combat the administrative state, on President Donald Trump‘s bad side.
In a series of lawsuits spanning trade, higher education, and legal ethics, historically conservative-leaning lawyers and libertarian public-interest groups are testing the limits of Trump’s executive authority during his second term. They argue that constitutional guardrails must apply regardless of who holds power.
This spring, former Solicitor General Paul Clement joined one of the highest-profile challenges: defending WilmerHale, a major law firm blacklisted by the Trump administration under an executive order targeting firms that represented disfavored clients. The administration accused WilmerHale of undermining national interests due to its past legal work and personnel ties to Robert Mueller’s special counsel investigation.
“There’s just no way to practice law under those circumstances,” Clement, solicitor general from 2004 to 2008 during former President George W. Bush’s administration, said during a March court hearing. A federal judge who heard the case swiftly issued a temporary injunction to halt enforcement of the order.
Clement’s conservative credentials are impeccable. He argued cases opposing gun control and against the Affordable Care Act, among others.
However, Clement is a vocal advocate of the principle that all legal clients, even those who are unpopular, deserve representation. Now, representing multiple clients who are challenging Trump administration actions, Clement is not alone. A growing list of conservative and libertarian-aligned attorneys are arguing that fidelity to the Constitution doesn’t evaporate when a Republican sits in the White House.
“We’re not just picking political sides,” Clement told a Federalist Society panel last year. “What we’re doing as lawyers is something different.”
One of the sharpest legal rebukes to Trump’s claimed authority comes from the New Civil Liberties Alliance, which has received donations from organizations tied to Federalist Society Co-Chairman Leonard Leo and Koch-affiliated networks.
With the help of Clement arguing before the Supreme Court, NCLA represented two clients last year that succeeded in overturning the 1984 Chevron doctrine, a precedent that for decades told courts to defer to agency interpretations of vague or ambiguous federal statutes so long as that interpretation was deemed “reasonable” by the judge overseeing the case. A 6-3 ruling last summer in Loper Bright v. Raimondo told lower courts to no longer defer to that practice, and instead interpret the law independently in a means to better balance the three independent branches of government.
Now, NCLA is fighting the Trump administration over what it sees as stretching the bounds of what Congress wrote under the International Emergency Economic Powers Act. The group also has sued in Pensacola, Florida, against Trump’s imposition of new tariffs on Chinese imports.
“This statute authorizes specific emergency actions like imposing sanctions or freezing assets to protect the United States from foreign threats,” NCLA wrote in an April 3 press release. “It does not authorize the president to impose tariffs.”
NCLA President Mark Chenoweth told the Washington Examiner that the administration’s legal justification is flawed from several angles.
“The statute doesn’t cover tariffs. It simply doesn’t mention tariffs,” he said.
Chenoweth argued that IEEPA was never intended to authorize taxation and that its use in this case would create a dangerous precedent.
“The pattern and practice under this statute is to treat it as though it doesn’t allow the president to use it for tariffs,” he said.
He also pointed to constitutional concerns and warned that allowing tariffs under IEEPA would “transfer core legislative power” without the necessary guardrails.
Chenoweth predicted the case would eventually reach the Supreme Court.
“It is of massive significance if the president has the power to unilaterally raise taxes on Americans — that would be news,” Chenoweth said.
The challenge to Trump’s executive power isn’t limited to trade. At Harvard University, officials have filed suit against the Trump administration’s efforts to restrict enrollment of international students and impose significant funding cuts to its research programs.
After refusing to comply with administration demands to fire faculty, restrict foreign students, and police campus speech, Harvard found itself in the crosshairs. Federal funding was frozen, and a threat to revoke the school’s tax-exempt status soon followed — a move defense attorneys said would violate the Administrative Procedure Act.
In response, Harvard assembled a cross-ideological legal team, including former clerks to Justice Clarence Thomas and a former Texas solicitor general who defended abortion restrictions.
But whether or not this lawsuit gets resolved from the bench is an open question as settlement talks linger, raising into focus that much of Trump’s disputes with college campuses have been forms of strong-arming these institutions into final agreements.
Trump recently said negotiations between his administration and Harvard are active.
“I think we’re probably going to settle with Harvard,” Trump recently told reporters at Joint Base Andrews. “They want to settle very badly.”
Raheem Williams, a researcher and policy analyst, said many conservative-aligned lawsuits reflect deep concerns over how executive power is being wielded. Not necessarily opposition to Trump’s policy goals, but disagreement over how to achieve them.
“Trump is pushing the bounds of executive authority in ways I agree with and ways I don’t,” Williams told the Washington Examiner. “In government, the means matter.”
He noted that conservative lawyers are thinking in “second- and third-order effects.”
“Let’s say Trump wins all these cases,” he said. “Now you’ve created a precedent for a very strong executive … So what happens when a Democrat has those powers?”
Trump’s crackdown on law firms has rippled across the legal profession. Executive orders targeting WilmerHale, Perkins Coie, Jenner & Block, and Covington & Burling have drawn scrutiny and criticism that they would inspire a culture in the legal practice that is fearful of speaking out against any potential imbalance of power.
In court filings representing these firms, Clement cited the tradition of John Adams defending British soldiers after the Boston Massacre.
“The rule of law cannot long endure in the climate of fear that such actions create,” he wrote.
But Williams disagreed that Trump’s executive orders are interfering with lawyers’ work or making them fearful to do their jobs.
“In a true environment of fear and retaliation, you would see almost none of this,” he said. “And when you do see it, it’ll always be anonymous — and that’s not where you’re at, thankfully.”
While some law firms with a history of avoiding conservative-backed causes or clients might prefer to capitulate to the Trump administration’s demands, such as pledging to contribute hours of work pro bono for conservative causes and clients, groups such as NCLA have shown no shyness when it comes to holding this administration accountable.
“We have heard through the grapevine [that] folks who have been on our side of this issue are unwelcome to apply for positions with the administration, but I’m not planning to do that anytime soon,” Chenoweth said of his firm’s challenge to Trump’s tariffs.
Some conservative legal groups are advancing cases that go further than the Trump administration itself, using lawsuits to pressure federal agencies into faster or more sweeping rollbacks of policies pursued by former President Joe Biden’s administration, particularly on diversity, equity, and inclusion.
For example, the Wisconsin Institute for Law & Liberty recently sued Agriculture Secretary Brooke Rollins over racially discriminatory loan guarantees and conservation subsidies, which it says still exist in USDA programs, despite Trump’s Day One directive to eliminate DEI. The group’s lawsuit followed months of warnings and support from Wisconsin’s Republican delegation.
Meanwhile, America First Legal sued the Department of Health and Human Services and its subagencies for refusing to release internal Biden-era records on race-based transplant policies. The group said such programs replaced need-based standards with race-conscious preferences and that transparency is essential to fully uproot them.
Williams contended these types of lawsuits are “doing the Trump administration a favor,” adding, “You’re not going to be able to just do it alone.”
In the case of NCLA’s tariffs challenge, Chenoweth said his firm is “looking to put constitutional guardrails in place, regardless of who is in charge of the administrative apparatus at any point in time.”
Though these lawsuits vary from issue to issue, each case carries far-reaching legal consequences. A ruling that IEEPA does not authorize tariffs could rein in the emergency economic powers Trump currently believes are at his disposal. A win for Harvard could reaffirm APA limitations. A judgment in favor of WilmerHale could clarify First Amendment protections for attorneys representing controversial clients.
Whether these challenges ultimately succeed remains to be seen. But the lawyers bringing them, such as Chenoweth, say the stakes go beyond party or policy.
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“We don’t have a position that he can’t do this as a matter of policy,” Chenoweth said, referring to the lawsuit on Trump’s China tariffs.
“I think he’s just gotten bad advice is how I would describe it,” Chenoweth added. “And I think we will try to make sure that [the administration] understands what the lawful way is to do, and hopefully they will course-correct.”
