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.

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........

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