Donald Trump shares important traits with one of his famous predecessors, Theodore Roosevelt. Like Teddy, Trump is thin-skinned and inclined to use the power of the presidency to punish political enemies.
In March 1906, when his political rival and Socialist Party standard bearer Eugene V. Debs wrote a scathing piece about Roosevelt in the socialist newspaper Appeal to Reason, Roosevelt asked his then-Attorney General William Moody, “Is it possible to proceed against Debs and the proprietor of this paper criminally?”
Moody had Assistant Attorney General Charles Robb determine whether Roosevelt’s request for legal action against Debs and the newspaper on libel grounds was feasible. It was not, Robb reported, but he suggested that it might be possible to criminalize “use of the mails in disseminating a criminal libel as this article undoubtedly is.”
Debs’ piece was an attack on Roosevelt’s policies and thus not remotely libelous, but the readiness with which Moody and Robb sought to find a facially legal way for Roosevelt to use governmental power to go after a political rival is just one of the chilling stories I recount in my new book, The Triumph of Fear: Domestic Surveillance and Political Repression from McKinley through Eisenhower.
During the balance of his presidency, Roosevelt used Secret Service agents to spy on his political opponents, both Democrats and Republicans. But it would be his administration’s misuse of those agents that ultimately triggered a bipartisan congressional backlash, resulting in the passage of a law in 1908 restricting the Secret Service to only protecting the chief executive and going after counterfeiters.
Undeterred, Roosevelt ordered his new Attorney General, Charles Bonaparte, to create a cadre of Justice Department agents out of whole cloth to continue the kinds of investigations Roosevelt sought. That new unit, established without congressional authorization, was known as the Bureau of Investigation – what we call today the Federal Bureau of Investigation.
Like Roosevelt, Trump is showing not only contempt for long-standing political norms, but for constitutional and legal constraints as well – often in service of his self-described “revenge tour.” The difference between the two men is that Trump is doing so on a scale never attempted by Roosevelt or any of his successors.
As Tom Dreisbach recently noted in a major NPR investigation of Trump’s actions in his first 100 days, “The list of targets now exceeds 100, according to NPR’s review, ranging from some of the United States’ most prominent Democratic politicians to international students who were unknown to the general public.”
Late on the evening of April 28, Trump issued several new executive orders, including one directing Attorney General Pam Bondi to publish within 30 days “…a list of States and local jurisdictions that obstruct the enforcement of Federal immigration laws (sanctuary jurisdictions). After this initial publication, the Attorney General and the Secretary of Homeland Security shall update this list as necessary.” Jurisdictions so designated will then be targeted with “suspension or termination” of federal funds.
Most ominously, those jurisdictions that, in the Administration’s view, “remain in defiance of Federal law” are to be targeted by the Justice Department with “all necessary legal remedies and enforcement measures to end these violations and bring such jurisdictions into compliance with the laws of the United States.”
These tactics hearkens back to the infamous Cold War-era “Attorney General’s List of Subversive Organizations” (AGLOSO), a due process-free mechanism used by the Truman and Eisenhower administrations against groups with alleged or actual ties to communist or socialist organizations. But unlike Truman or Eisenhower, Trump’s de facto “enemies list” goes beyond targeting of civil society elements like law firms and universities. Trump is now going after other governmental elements within the American federal system and asserting unilateral power to do so.
But presidents and their chief law enforcement officers do not determine what the law is or is not, or who is violating federal laws or the Constitution itself. In our system of government, that role is reserved exclusively for federal courts, and in the final instance, the Supreme Court. Some term Trump’s defiance of federal court rulings a “constitutional crisis.” It is not.
When the federal chief executive is openly defying courts and federal law enforcement agents are carrying out his policies in defiance of those same courts, it represents “constitutional breakdown,” particularly when Trump’s party controls Congress and precludes any legislative action to stop his lawlessness.
In just 100 days into his second term, Trump has easily eclipsed the constitutionally dubious antics of Teddy Roosevelt. He has, in fact, created the most dangerous domestic political powder keg since April 1861. One thing is certain. The America that emerges from this growing constitutional and political calamity Trump has created will not be the same as the America that entered it.
Former CIA analyst and ex-House senior policy advisor Patrick G. Eddington is a senior fellow at the Cato Institute and the author of The Triumph of Fear: Domestic Surveillance and Political Repression from McKinley Through Eisenhower (GU Press, 2025).
