Trump took specific actions that will be very popular. Sure, law professors can fight over the separation of powers issues. But the people who benefit from these policies will gladly, or perhaps begrudgingly, accept the money. The optics for legal challenges are bad. Will the House of Representatives go to court to ensure that people have to pay taxes? Will states go to court to block people from receiving unemployment benefits? Will landlords go to court to make it easier to evict people? Will lenders go to courts to ensure that student loans are paid? Trump’s strategy is diabolical.

Trump also put Vice President Biden in a tough spot. All of these orders expire in December 2020. Trump said if he is re-elected, he would continue the policies, and forgive some of the loans. What is Biden going to do? He favors the policy, opposes the executive actions, and prefers legislation? Again, law professors love those sorts of arguments. I have been repeating that line for years with respect to DACA. But average people will not be happy with it. Biden is stuck between a rock and a hard basement.

One final note. The biggest losers today are employers. Will corporations actually stop withholding payroll taxes? Sure, Trump approved that action. But federal law remains in place. Will any compliance department actually stop withholding payroll taxes on the promise of an executive action? A Biden administration could prosecute these companies. Thus, employers will now be at odds with their employees who demand their full salary. Perhaps an employer would be a good litigant to challenge this executive action, as there is no regulatory uncertainty.