Through executive actions targeting lawsuits and law firms, President Donald Trump is attempting to undermine legal challenges to his authority while retaliating against those who stand in his way.
President Donald Trump has issued a new executive order that seeks to limit legal challenges to his administration’s actions by leveraging Federal Rule of Civil Procedure 65(c)—a little-known law that allows judges to require plaintiffs to place financial securities upfront if they seek an injunction against government actions.
Trump’s order directs federal agencies to aggressively request these financial securities when lawsuits challenge his executive actions. Under this rule, if a plaintiff secures an injunction against an executive order and the injunction is later overturned, the plaintiff could be required to pay the federal government’s legal fees upfront.
The administration justifies the order by arguing that it protects taxpayer dollars from “activist organizations” that pursue lawsuits only to lose them in higher courts. However, the measure functions as a deterrent against lawsuits, creating financial risk for those seeking to block executive actions.
In the order, Trump falsely describes these legal challenges as an “anti-democratic takeover” by “forum-shopping organizations that repeatedly bring meritless suits, used for fundraising and political grandstanding, without any repercussions when they fail.”
While the executive order directs agencies to seek security payments, it does not guarantee that courts will impose them. Judges retain full discretion under Rule 65(c), and many have declined to require bonds from plaintiffs challenging government actions.
One example is a recent case involving Trump’s executive order restricting gender-affirming care for transgender youth. When the administration sought to impose financial security on the plaintiffs, U.S. District Judge Brendan Hurson refused, writing:
“Because the Court has found that Plaintiffs are likely to succeed on their claim…the Court again declines to require a bond.”
Legal experts believe courts will likely continue rejecting these financial security requests, making the executive order more symbolic than effective. Jeff Overley, editor-at-large for Law360, stated that while small advocacy groups may hesitate to sue due to the financial risk, it is unlikely that courts will broadly impose large financial securities on lawsuits.
“It’s entirely possible the memo could give pause to small groups interested in suing the Trump administration…Generally speaking, however, there are reasons to doubt that Thursday’s memo will be a big deterrent.”
Despite this, the intent of the order is clear: it signals that the administration will aggressively push back against legal challenges, regardless of their merit.
In a separate but related move, Trump issued executive orders targeting two major law firms, Perkins Coie and Covington & Burling, which have represented opponents of his administration.
• Perkins Coie represented Hillary Clinton’s 2016 presidential campaign and has been involved in election-related litigation.
• Covington & Burling currently represents Special Counsel Jack Smith, who brought criminal charges against Trump in two federal cases.
The executive orders:
✅ Revoked security clearances for attorneys at these firms.
✅ Restricted the firms’ access to federal buildings.
✅ Ordered a review to terminate their federal contracts.
Trump’s order accused Perkins Coie of “dishonest and dangerous activity” and claimed the firm “racially discriminates” in its hiring due to its diversity initiatives. Trump’s allies have repeatedly portrayed corporate diversity efforts as discriminatory against white people.
Covington & Burling responded by emphasizing their long history of legal representation:
“For more than 100 years, Covington has represented clients facing government investigations, consistent with the best traditions of the legal profession.”
Perkins Coie called Trump’s actions “patently unlawful” and pledged to challenge them in court.
Legal scholars warn that Trump’s targeting of law firms may be unconstitutional, violating both the First and Fifth Amendments.
• First Amendment Violation: By targeting law firms based on the clients they represent, Trump’s order could be a case of government retaliation against protected speech.
• Fifth Amendment Violation: University of Toledo law professor Evan Zoldan notes that Trump’s order lacks due process, as Perkins Coie was not given notice or an opportunity to challenge the allegations before losing security clearances and federal contracts.
University of Pennsylvania law professor Claire Finkelstein emphasized that the security clearances in question are critical to the firms’ ability to represent certain clients:
“By removing these security clearances, they have removed a piece of their livelihood, and they’ve done that without due process of law.”
Mark Lemley, a professor at Stanford Law School, called Trump’s actions a “blatant example of viewpoint discrimination”, arguing that the executive order punishes law firms for representing clients that Trump politically opposes.
The American Bar Association (ABA) also condemned the move, warning that it could have a chilling effect on legal advocacy. ABA President William Bay stated:
“The government has decided to punish two prominent law firms because they represent parties that the administration does not like.”
Trump’s executive orders are part of a broader pattern of using government power to attack opponents and shield himself from legal accountability.
• Weaponizing federal agencies: Trump has repeatedly used government power to retaliate against perceived enemies, including prosecutors, judges, and intelligence officials.
• Eroding legal protections: By making legal challenges financially risky, Trump is attempting to limit opposition to his executive power.
• Authoritarian precedents: If these tactics go unchallenged, future presidents—Republican or Democrat—could expand executive power to punish legal opponents.
UCLA law professor Jon Michaels highlighted the dangerous precedent:
“Trump swore up and down that he’d seek ‘retribution’ against his political opponents.”
What comes next?
• Judicial response: Courts may rule on the constitutionality of these orders, particularly in cases where security clearances or federal contracts are revoked without due process.
• Legal firm reactions: Firms like Perkins Coie and Covington & Burling are expected to challenge Trump’s actions in court.
• Congressional oversight? Democrats and some legal advocacy groups may push for investigations into Trump’s use of executive orders.
Trump’s latest executive orders go beyond typical political maneuvering—they represent an effort to intimidate and punish those who challenge his authority.
While courts may ultimately reject his financial security directive, the threat of retribution against law firms is a serious escalation in Trump’s pattern of attacking the legal system.
If legal opposition to government overreach is financially and professionally risky, who will hold the executive branch accountable in the future?
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