How Trump Keeps Exploiting America’s Legal Loopholes
· Time
In his first term, legal experts reassured us about the invincible sanctity of our democratic and legal processes that President Donald Trump regularly attempts to exploit. But in his second term, Trump has been much savvier about the guardrails that stopped him in the past by exploiting legal loopholes. Many CEOs say they believe in investing where there is the rule of law, not the law of rulers, but what if they become one and the same because of a president’s underestimated, if devious, cleverness?
Relying on the Constitution as a meaningful guardrail demands an underlying, almost pious belief in the good faith of political actors adhering to a shared set of values and processes enshrined in the Constitution. America’s Founding Fathers believed in checks and balances, but they also believed that the people who would hold public office would demonstrate both private and public virtue.
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But when it comes to shared sets of values and processes, Trump is a nonbeliever. He worships only himself. Where constitutional scholars see a rigid procedural process of checks and balances, Trump sees a catalog of vulnerabilities, loopholes, and acceptable penalties to be gamed for personal advantage, as Sonnenfeld and Tian write about in the bestselling book, Trump’s Ten Commandments.
In his 1835 treatise Democracy in America, Alexis de Tocqueville observed that the U.S. legal system was designed for adaptability, but anchored by an underlying expectation of moral restraint. He noted that "in the formation of the laws, it has been given the means to follow the natural instability of its inclinations." For roughly 240 years, the Constitution has held strong because political leaders have generally colored within its lines in good faith, keeping faith in the process, as described by Yale Law professor John Witt.
Even rogue actors ultimately respected institutional boundaries and were constrained by the system; for example, Richard Nixon resigned when confronted with the likelihood of impeachment by the Senate. But Trump views that as a pathetic weakness, frequently contending that Nixon’s biggest mistake was that “he didn’t fight” and that foolishly “he left.”
Instead, Trump channels the spirit of Andrew Jackson, whose painting Trump brought into the Oval Office during his first term. Following the 1832 Supreme Court decision in Worcester v. Georgia, in which Chief Justice John Marshall ruled that states had no legal authority over sovereign Cherokee territory, Jackson apocryphally scoffed, “John Marshall has made his decision; now let him enforce it.”
And indeed, the history of that episode is a chilling illumination of what happens when political leaders color outside the lines drawn by the Constitution. Because Jackson refused to use executive power to enforce the Court’s protections, Cherokee sovereignty was violated with impunity, ultimately paving the way for the brutal, infamous Trail of Tears. All the legal experts who swear by the inviolability of Constitutional procedures should perhaps ask the Cherokee people how they’re enjoying their indigenous lands, which have been taken from them.
Perhaps the most alarming truth of all is that many of Trump's biggest offenses against democracy are not technically illegal. They are legal exploitations of systemic loopholes. Indeed, aside from whatever laws some believe Trump has broken, he has astoundingly found and exploited huge loopholes in existing laws and processes for his own advantage, with huge consequences for democracy.
While some believe that Trump is merely the conduit for devious legal advisors, his legal advisors say otherwise, giving Trump the credit for pushing them to try unorthodox angles. Thus, when we watch his legal maneuverings in various courtrooms, we see his various personal lawyers simply doing exactly what they are told. In truth, the best attorney Donald Trump has ever known is himself.
Trump’s legal loopholes
Consider some startling examples of how Trump has legally exploited structural vulnerabilities and statutory loopholes to consolidate executive power as president.
Take how Trump has gained greater war powers. There is probably no authority in the Constitution that has been as expansively interpreted, and employed, as the Commander in Chief Clause of Article II. Although the trend of accreting power to the executive branch began well before Trump became president, his current administration has taken it to the next level, claiming unilateral war powers even in the absence of congressional approval.
Then, there is how Trump delegates congressional authority. Many of the most controversial powers Trump has used this term do not even fall directly under his Article II authority. Rather, they are powers assigned to Congress that have been delegated to the president so he can respond quickly to real threats such as terrorist attacks, foreign invasions, or internal rebellions. But by creatively defining these terms like “terrorism,” “invasion,” and “rebellion,” Trump has deployed these delegated powers more broadly than ever before. These include the power to revoke visas for international students and remove foreign nationals under the Alien Enemies Act, or to deploy the National Guard and the military in D.C. and in several states.
Relatedly, there is the way Trump directs law enforcement. Critics argue that Trump has turned the Justice Department and the FBI into his personal law firm, doing his bidding. The Supreme Court has interpreted this power almost as expansively as his war powers: In its immunity decision, it held that the president was “absolutely immune” from criminal liability for official acts. He has clearly taken that to heart.
This power is evident in how Trump maintains control over all executive branch employees. The so-called “unitary executive” theory vests “all the executive power” in the singular person of the President. That means that Trump sees everyone who is subordinate to him, from cabinet officials to civil servants, as just little mini-mes whom he can hire and fire at will. Trump has wielded this theory to fire inspectors general, prosecutors, FBI agents, among many others.
Meanwhile, Trump has leveraged a carousel of acting cabinet members to his own benefit. Trump has always relied upon interim appointments as much as possible, given their filial piety of the office holder to Trump, as their legitimacy is anchored only by his authority and not Congressional confirmation. The Constitution explicitly mandates that the Senate must "advise and consent" on high-level cabinet appointments, but Trump effectively neutralized this requirement by exploiting the Federal Vacancies Reform Act (FVRA). The law allows the president to appoint "acting" officials for a temporary period (typically 210 days). By continually rotating a cast of unconfirmed loyalists through the highest levels of government, Trump’s interim appointees are able to enact highly controversial policies without ever subjecting them to Senate hearings, public scrutiny, or congressional oversight. When an acting secretary's time limit expired, or if they pushed back on his demands, he simply fires them, endlessly resetting the clock and effectively centralizing all power in his own hands.
Similarly, Trump initially exploited the International Emergency Economic Powers Act (IEEPA) to impose sweeping, unilateral tariffs. But after the Supreme Court invalidated IEEPA, Trump pivoted to a legal game of whack-a-mole. Almost immediately after the ruling, he simply rotated his legal justifications, announcing new universal tariffs under alternative authorities and citing different sections of the Trade Act to achieve the exact same goal, burying the courts and Congress in an endless cycle of new litigation, proving that when the judicial system finally closes one loophole, he simply bypasses the ruling by exploiting another.
Another loophole Trump leverages to achieve his all-encompassing power grab is the National Emergencies Act. The Constitution explicitly grants the "power of the purse" to Congress. When Congress repeatedly refused to fund Trump's border wall, he bypassed the legislative branch entirely by exploiting the National Emergencies Act of 1976. Because the Act provides incredibly broad definitions of what constitutes an "emergency," he legally redirected billions of dollars in military construction funds to his domestic political project. The National Emergencies Act can also trigger other “standby” authorities, like IEEPA, allowing him a one-two punch.
He has also used the ambiguity of the 1887 Electoral Count Act to his own advantage. Following the 2020 election, Trump and his legal team exploited poorly drafted, 19th-century language in the Electoral Count Act. As prominent Harvard Law professor Laurence Tribe and conservative jurist Michael Luttig argued, the archaic law was dangerously flawed and fundamentally ripe for partisan exploitation. Because the original statute did not explicitly define the Vice President's role during the certification of electoral votes as strictly administrative, Trump's allies were able to build a pseudo-legal theory that former Vice President Mike Pence had the unilateral authority to reject state electors. Luttig publicly warned that unless lawmakers stepped in to fix the text, bad-faith political actors would simply use the exact same ambiguous framework to subvert future presidential elections—a genuine constitutional loophole Congress was finally forced to close with the Electoral Count Reform Act of 2022.
This is the same style in which Trump has taken advantage of the lack of limits on pardon power. The U.S. Constitution grants the president virtually unchecked authority to issue pardons, with no built-in limits. Trump used this loophole to bypass traditional Department of Justice vetting processes, granting unprecedented clemency to political allies, campaign associates, and potential witnesses (such as Roger Stone and Paul Manafort), in ways critics argue effectively neutralize the pressure on them to cooperate with federal investigators, which the Constitutional framers surely never imagined.
This takes us to Trump’s “run out the clock" subpoena strategy. Congressional oversight relies on the ability to subpoena documents and testimony. However, Trump realized that Congress has no independent enforcement arm; it must rely on the Department of Justice or the slow-moving federal courts. By asserting incredibly broad "absolute executive privilege" over virtually every administration official, Trump exploited the sluggish pace of the judicial system, tying up congressional subpoenas in court for years until the legislative term ended and the investigations expired.
Trump has likewise exploited gerrymandered redistricting, primaries drawing small turnout or most of the extreme party members, combined with presidential endorsement of loyalists, and Congressional passivity. Faced with these grotesque imperial extensions of Article II of the Constitution, Trump’s many critics contend that Article I and Article III of the Constitution need to work together quickly to fortify each other before further Constitutional atrophy.
So long as the aforementioned legal loopholes exist, Trump is likely to continue exploiting them.
Bankruptcy, tax evasion, and legal ambiguity
To be sure, none of this is new behavior for Trump. He has long leveraged the same loophole-driven approach in his personal and business life, far before his initial descent down the golden escalator of Trump Tower in 2015. As Trump proudly bragged when confronted by journalists about his bankruptcies, “What I’ve done is I’ve used, brilliantly, the laws of the country.” Consider how he systemically and legally exploited legal loopholes to his personal advantage in his business affairs.
Strategic Chapter 11 corporate bankruptcies: Between 1991 and 2009, Trump's companies filed for Chapter 11 bankruptcy protection six times (mostly involving Atlantic City casinos). By exploiting loopholes in corporate restructuring laws, he largely protected his personal wealth while shifting large losses to banks, bondholders, and contractors, all while keeping his name on the buildings.
The net operating loss tax loophole: As revealed by his own tax disclosures, Trump reported a staggering $916 million loss on his 1995 tax returns. Exploiting tax codes regarding net operating losses (NOL), this massive single-year business loss allowed him to legally avoid paying any federal income taxes for up to 18 subsequent years. Similarly, those tax returns reveal that Trump and his family minimized their estate taxes by transferring wealth through various legal structures, such as setting up a family-controlled contracting firm to divert profits from the Trump Organization.
Emoluments Clause ambiguity: During his presidency, Trump retained ownership of his many businesses. While the Constitution’s Emoluments Clauses forbid a president from taking gifts or profits from foreign or domestic states, the lack of a clear statutory definition or enforcement mechanism allows his businesses to legally do business with foreign governments in spades.
When it comes to finding legal loopholes, Trump has an uncanny ability to weaponize time itself, exploiting every procedural mechanism available—filing endless interlocutory appeals, demanding venue changes, and launching collateral attacks—to effectively paralyze the courts. In Florida, he successfully leveraged endless procedural hearings to indefinitely delay and ultimately derail the classified documents case. And in New York, he repeatedly outmaneuvered prosecutors to delay sentencing in his criminal hush-money case and freeze massive civil fraud penalties, until he was ultimately let off the hook entirely.
In his 1707 piece, A Critical Essay upon the Faculties of the Mind, Jonathan Swift remarked, “Laws are like cobwebs, which may catch small flies, but let wasps and hornets break through.”
It is time for Trump’s many critics to wake up and realize that, despite his public buffoonery, they are not dealing with a bumbling village idiot tripping over rules through ignorance. Rather, he is a wasp who pushes the law’s limits. As long as some experts, political pundits, and congressional leaders maintain their antiquated faith in the cobwebs of process, relying on the good faith and shared values, Trump will continue to burst through America’s democratic safeguards.