Trump’s 'try again' legal strategy has experts sounding the alarm

President Donald Trump outside in the White House Rose Garden on April 2, 2025 (Official White House Photo by Daniel Torok/Flickr)

Former FBI General Counsel Andrew Weissmann and former Acting Assistant Attorney General for National Security Mary McCord spoke out about what they see as a recurring strategy of the Donald Trump administration.

Speaking on Tuesday for their podcast, the two legal eagles note that Trump continues to pursue contested policies despite legal losses.

"I call this episode, 'If at first you don't succeed, try, try again,'" McCord said about Trump's legal strategy.

A recent Supreme Court decision lifted one of two lower-court orders blocking Trump’s executive action aimed at restricting mail voting. Weissmann emphasizes that the Court’s ruling was procedural, based on ripeness, meaning the justices concluded the challenge was brought too early, not a decision on whether Trump’s order is lawful. Weissmann said that he expects the dispute to return to the Supreme Court for a ruling on the merits.

Weissmann argues that Trump's executive order could have a disproportionate effect on specific voters through restrictions involving the the Postal Service. To illustrate his concern, he offers a hypothetical similarity: What would happen if a president barred the Postal Service from distributing ballots to people perceived as Democrats, or, alternatively, Republicans? In his view, the current order operates as a proxy for a similarly discriminatory outcome, and he worries that language in the Court’s recent decision signals the justices may eventually permit it.

Weissmann recalled Trump's big announcement that they found "all of this illegal voting and ... And then, when you actually looked under the hood, or, in this case, looked at exactly what they were saying, it wasn't there. I mean it was — it was literally — there was no support for it."

The lawyers explained that so much of that case has ended in litigation.

McCord agreed, saying that Section 2A, "directed the Department of Homeland Security to put together a list of citizens in each state who would be 18 years old at the time of the next election and send these out to the states so that they would have this state citizenship list, supposedly just so that states would have them to do whatever they wish."

"Yet, when in section 2B, it says they're prioritizing investigation and, as appropriate, the prosecution of state and local officials who might allow someone who is a non-citizen to vote. And the rhetoric that came with this executive order was very much, we're going to tell you who's a citizen, and if you, state election officials, let somebody vote who's not on that list, we're going to investigate you," McCord characterized.

The "overlay," they described, is that the administration likes to report a "spectre of illegal voting" breaking out all over the U.S.

Trump's other battle is his new order to eliminate birthright citizenship for a second time. That EO has already been shot down by the U.S. Supreme Court. So, "If at first you don't succeed..."

The lawyers explained that the plaintiffs have filed a new motion asking a district court to reject the revised orders. He argues that the new restrictions should fail under the reasoning of the Court’s prior ruling.

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