Rex Tillerson, James Mattis, and Kirstjen Nielsen watch Donald Trump speak in 2018.Andrew Harnik / AP

Donald Trump has cut through old norms like a combine through wheat at harvest. Courts have sometimes restrained him, though they’ve more often just slowed him down. Congress, now under Democratic management, has begun to bark, but hasn’t yet shown any bite.

But the president’s frustrations over recent border stories show that the law remains the one persistent barrier to the president’s ability to put his desires into practice. When government officials have concluded that they’re receiving unlawful orders, they’ve generally refused them. Both Kirstjen Nielsen, who was subsequently forced out as secretary of homeland security, and Kevin McAleenan, her acting replacement, blocked a plan to prevent migrants from seeking asylum on the basis that it violated laws passed by Congress. Another plan, to bus unauthorized immigrants to so-called sanctuary cities that don’t cooperate with federal immigration authorities, met a similar end. Officials at Immigration and Customs Enforcement determined that the retributive plan wouldn’t be a justified use of funds and could create new liabilities, according to The Washington Post and The New York Times.

The big difference between Trump and his aides, especially on immigration, isn’t ideological. His lieutenants tend to agree with him on outcomes. But they at least have some commitment to following the law in trying to achieve those outcomes, whereas he does not.

In his desire to circumvent rules he doesn’t like, Trump is hardly alone. Presidents have long found ways to get around laws they don’t agree with. They’ve had the Office of Legal Counsel concoct some sort of justification for how they are really following the law; they’ve argued that the law they don’t like is actually unconstitutional. Barack Obama’s administration contorted itself to justify the killing of an American without due process; George W. Bush’s administration did the same to allow torture. (The old-school approach survives in Treasury Secretary Steven Mnuchin’s handling of a congressional request for Trump’s tax returns. Mnuchin seems to be slow-walking the request while seeking legal analysis.)

As with most such niceties, Trump has no interest. Consider the attempt to bar asylum seekers. Rather than claiming that doing so was actually justified, Trump reportedly told McAleenan that if McAleenan were jailed for breaking the law, he’d receive a presidential pardon. Even if the statement was made in jest, it was a remarkable acknowledgment that Trump assumed what he was ordering was illegal.

It would be nearly as remarkable that McAleenan and Nielsen refused to go through with the order, if not for the fact that so many of their colleagues have done the same. For example, former White House Counsel Don McGahn said he would resign rather than fire Special Counsel Robert Mueller, a move he thought might constitute obstruction of justice. Often officials end up instituting a much more limited, and more legally defensible, version of what Trump demands. Former Defense Secretary James Mattis balked at an initial order to ban transgender troops from the military, which might have had no rational basis under law, but he eventually put in a place a more limited ban. When Trump wanted to send thousands of troops to the border to counter an illusory “invasion” just before the 2018 election, Mattis complied. But he made sure that troops were not actually apprehending migrants, as Trump seemed to want, but were instead acting in a legally sanctioned support role.

The Trump Organization makes for a useful contrast, both today and historically. While government officials have flinched at implementing orders they think might violate the law, the company has not—showing no compunctions, for example, about taking money from foreign or state governments, at the risk of violating the Constitution’s emoluments clause.

Moreover, the company’s history of doing business may help explain Trump’s cavalier attitude toward potential violations of the law. The Trump Organization under Donald Trump’s leadership was a legendarily litigious entity. It broke rules, regulations, and contracts, then fought claims against it in court. Sometimes that meant settling a lawsuit, either with the government or a contractor; other times it meant plaintiffs deciding that suits were too expensive to pursue.

In 1973, for example, the Department of Justice sued Trump Management—for which Donald Trump then served as president—for violating the Civil Rights Act by discriminating against blacks. A New York Times investigation in 2016 alleged a long history of racial discrimination at the Trump family’s properties. But Trump vigorously fought the suit, and ultimately settled it without admitting wrongdoing.

But what works well for a private business with a multimillionaire or billionaire boss, which can afford big legal bills, doesn’t work as well for a government official, who faces the end of a career, financial ruin, or even jail if he or she behaves the same way. The president welcomes litigation, but his deputies fear it.

There’s a counterintuitive argument to be made that Trump’s way of flouting the law is healthier than the previous method. Whereas presidents have historically done what they wanted while hiding behind flimsy legalistic fictions, Trump is being considerably more straightforward. He lies repeatedly, but there’s a greater truth about how he’s operating. (I am reminded of a certain 2016 New Yorker cartoon.) And when his directives push beyond the boundaries of the law, he’s more easily constrained than his predecessors, who armored such directives with legal memos and counsel’s opinions.

But of the officials cited here, only McAleenan remains, with Nielsen, McGahn, and Mattis out the door. The question now is whether administration officials will continue to refuse to execute illegal orders, or whether Trump will eventually manage to surround himself with aides prepared to act without regard for the law.

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