Conservatives explain why Trump's judicial losing streak won't stop

U.S. President Donald Trump looks on as he speaks to members of the media aboard Air Force One en route to Joint Base Andrews, Maryland, U.S., March 29, 2026. REUTERS Elizabeth Frantz

President Donald Trump has lost legal battles, even with courts dominated by his judges, on issues from his tariffs and attempts to control mail-in ballots to his attempt to overturn a civil verdict which found he sexually abused journalist E. Jean Carroll. According to a pair of conservative commentators at The Bulwark, these failures can be explained by a simple fact:

Trump and his advisers keep bungling American law.

“The government has always had the legal authority to subpoena journalists when there's classified national security information that gets leaked,” The Bulwark’s Ben Parker said on Thursday. “And traditionally, they don't. There are a few reasons for this. One of them is, it's got some First Amendment implications. The other one is the government would, honestly, most of the time, rather have a good relationship with the press than constantly be hounding them with subpoenas and maybe criminal investigations and stuff. And so usually it's the people who are leaking the information, rather than the journalists, who are at the end of the criminal investigation process.”

Parker added, “The Trump administration decided, ‘Nope, we're gonna subpoena not only these journalists, but also apparently their family members.’ And so the court said, like, ‘Hey, why don't you slow down, take a beat, and try saying please first?’ It's not illegal for them to bring these subpoenas. They could try again after they go through some other process, but it is like, ‘Hey, guys, slow your roll here a little bit.’”

The Bulwark’s Sam Stein added that Trump was “supposed to exhaust other processes to try to investigate the leak of that information before going to the subpoena. They did not.” Parker added that the Trump administration could have done more damage if they had merely been a little more careful. As another example, they turned to the Trump administration’s failed attempt to get information about Jewish students at the University of Pennsylvania.

“The other one was — again, another thing the administration was forced, after a long legal battle, to quietly retract,” Parker told Stein. “You may remember this from the deluge of 2025 Trump administration craziness. They had asked the University of Pennsylvania for a list of all of its Jews, basically. They said — ‘I'm not gonna do the voice. I'm not gonna do a German accent, I promise’ — they said, ‘We're investigating antisemitism. Would you please give us a list of all of your Jewish faculty in the Jewish studies program, all of your Jewish cultural, religious, whatever organizations, and all of the people who belong to those organizations? Please give the government a list of your Jews.’ And the school, to its credit, said, ‘No.’”

After both men laughed, Parker continued that “after a long fight, the administration has said, ‘Okay, we are no longer requesting a list of your Jews. Thank you very much.’”

Stein commented that "it's a remarkable string of losses" and Parker added that Trump’s administration would have anticipated this if they understood how conservatives — even those he appointed — tend to view the law.

“A lot of these Trump-appointed judges from his first term are the ones smacking down what he's doing now, because they're sort of pre-Trump ... Federalist Society types,” Parker explained. “And they're saying, ‘No, you can't just take a state's voter rolls. What the hell are you talking about?’”

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