'That's a lot of losses': Expert breaks down ways Trump has been 'the biggest loser'

06 September

U.S. President Donald Trump speaks during a dinner for lawmakers on the newly renovated Rose Garden patio, at the White House in Washington, D.C., U.S., September 5, 2025. REUTERS/Brian Snyder

President Donald Trump and his appointees — including Vice President JD Vance, U.S. Attorney General Pam Bondi and Homeland Security Kristi Noem — are having an intense battle with many legal scholars over the executive powers that presidents have under the U.S. Constitution. Trump, Bondi and Vance are claiming that lower federal courts have no business issuing injunctions against so many of his executive orders, but many legal experts — including former federal prosecutors Joyce White-Vance, Barbara McQuade and Kimberly Wehle — counter that scrutinizing Trump's executive orders is exactly what federal courts are supposed to do under the United States' system of checks and balances.

In a September 5 newsletter for The Nation, progressive legal expert Elie Mystal praises lower federal court judges for blocking Trump orders they consider unconstitutional. And he notes that Trump has recently been — to borrow Gavin Newsom's words — "the biggest loser" in federal court rulings.

"The Trump Administration repeatedly lost in court this week," Mystal observes. "A federal judge in California ruled that Trump violated the Posse Comitatus Act when he deployed federal troops to Los Angeles. A federal judge in Massachusetts ruled that Trump violated the law when he attempted to cut off federal funding to Harvard. The Court of Appeals for the Federal Circuit ruled that most of Trump's tariffs are illegal. And a panel of judges from the Fifth Circuit Court of Appeals — the most conservative and reactionary appellate court in the country — ruled that Trump’s targeting of Venezuelans was an illegal use of the Alien Enemies Act."

Mystal continues, "That's a lot of losses. Donald Trump continues to be the losingest president in court in American history. He is the biggest loser."

But according to Mystal, there is a huge caveat.

These recent losses, Mystal stresses, are in the lower federal courts — whereas the U.S. Supreme Court has been quite favorable to Trump.

In their controversial decision in Trump v. the United States, the U.S. Supreme Court ruled that presidents enjoy absolute immunity from prosecution for "official" but not "unofficial" acts committed in office. Justice Sonia Sotomayor, a Barack Obama appointee and one of the dissenters in that case, warned that Trump could order the assassination of a political rival and get away with it by claiming it was an "official" act.

"None of these losses are final," Mystal says of the recent lower federal court rulings against Trump. "Every single one of these cases will be appealed to the Supreme Court, and we all expect the Supreme Court to reverse these decisions to further the president's MAGA agenda. Trump also expects that. He's not even pretending to be chastened by his losses. He's not firing his lawyers and demanding better service. He's going to go to the Supreme Court and expecting them to do his bidding, which they almost certainly will."

The attorney continues, "The president lost four court cases in a week, and none of it matters. That is the evidence that we're living in an autocratic dystopia."

Elie Mystal's full newsletter is available at this link (subscription required).

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