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.

Quinta Jurecic: Trump’s unpardonable challenge to the Constitution

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.