Christopher Lasch, a law professor at the University of Denver, says the president's legal tactics reveal his underlying approach to the law -- more as a businessman conducting a cost-benefit analysis than as a constitutional officer sworn to uphold it.
"He very much understands the law in this instrumental way -- how much do I have to gain, how much do I stand to lose," Lasch said.
"The view there seems to be that there is going to be a push for policy and agenda regardless of what the law says," Lasch added. It's a win-win, the professor argued, because even if the president loses a legal round, his willingness to blaze ahead continues to energize his base.
Nunez pushed back on the notion that Trump is pandering to those who voted him into office.
"What he's doing is trying to fulfill promises he made to the American public on these issues, in spite of courts that have been generally hostile to anything and everything he's done and a Congress that's refused to do a single thing to alleviate any part of this problem," Nunez said.
Here is a look back at some of Trump's major immigration policies, and how they've fared.
Remain in Mexico
The Trump administration's latest legal loss came last week when a San Francisco federal judge blocked a program that sent hundreds of asylum-seekers back to Mexico to await their immigration court hearings in the United States.
The program, called Migrant Protection Protocols but known widely as "Remain in Mexico," was designed to prevent the surge of Central American asylum-seekers from waiting out their immigration cases in the U.S. -- either in detention or while released into the community. The government has argued that detention facilities are overcrowded, and many migrants who are released melt into the interior and fail to show up for court.
The program was piloted in January at the San Ysidro Port of Entry and has since expanded to other parts of the southwest border.