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Donald Trump is learning that appointing judges doesn't always guarantee wins

It’s hard to rate which legal news was worse for Trump last week.
Photo illustration: Image of Donald Trump between red and blue paper pieces and the backs of two judges.
Last week brought a seemingly relentless deluge of legal news for former President Donald J. Trump.MSNBC / Getty Images

Last week brought a relentless deluge of legal news for former President Donald J. Trump. All of it was bad, and some of it came courtesy of judges he or former Republican President Ronald Reagan had appointed.

Judge Raymond J. Dearie, a Reagan appointee who is serving as a special master to review documents the FBI seized during its August search of Trump’s Florida home, has been appropriately skeptical of the Trump team’s legal tactics and demanded Tuesday that Trump’s attorneys back up some of Trump’s claims with evidence. Then, the next day, a three-judge appellate court panel with two Trump appointees rolled back a previous ruling that had wrongly gone Trump’s way.

Last week brought a relentless deluge of legal news for former President Donald J. Trump. All of it was bad.

The above doesn’t even include the lawsuit New York Attorney General Letitia James filed accusing Trump and the Trump Organization of civil fraud. That civil case threatens to undermine the fairy tale that Trump is a successful businessman worthy of our trust as the leader of the free world. The criminal investigation into how documents the Department of Justice says are sensitive ended up at Trump’s Florida home could threaten the freedom of whoever is implicated. And Americans aren’t wrong to worry about how Trump stacking the judiciary might come into play.

But the rulings related to the FBI’s search of Mar-a-Lago show that there’s something to Chief Justice John Roberts’ statement: “We do not have Obama judges or Trump judges, Bush judges or Clinton judges. What we have is an extraordinary group of dedicated judges doing their level best to do equal right to those appearing before them.” Roberts made that statement in 2018, in response to an angry Trump dismissing a ruling against his administration as having come from an “Obama judge.”

Reader, I can hear you from here. You’re yelling at me that my argument is hogwash (only you won’t use that word) and that all we need to do is look at the Supreme Court to see just how much Republican-appointed federal judges have shaped, often for the worse, our country. Remember, you’re saying, when women had a constitutionally protected right to obtain an abortion? I do remember, and I agree that thanks in part to the three Supreme Court justices Trump appointed that right no longer exists.

But it’s also true that federal judges appointed by Republicans don’t always rule in ways that hand Republican politicians political wins. In the aftermath of the 2020 election, Trump and his boosters brought baseless lawsuits throughout the country. They were uniformly rejected by judges of both political stripes.

On Wednesday, at the 11th U.S. Circuit Court of Appeals, a three-judge panel, made up of two Trump appointees and one Obama appointee, handed Trump a significant legal setback. The three judges unanimously clapped back at an egregiously wrongheaded opinion written by U.S. District Judge Aileen Cannon, who had ruled that the Justice Department had to pause its examination of classified documents found at Mar-a-Lago. The three appellate judges concluded that, contrary to Cannon’s ruling, the DOJ could continue using the documents marked as classified that were found at Trump’s home and that the special master did not need to review those documents.

Trump’s legal team had fared no better Tuesday, the day before, during the first hearing Dearie held as special master. It was Trump, of course, who had asked for a special master to review the documents for attorney-client privilege issues (which the Justice Department’s filter team had already done) and executive privilege issues (which can’t legally exist in this scenario). Trump put forward two names of people to serve in the role of special master, and the DOJ agreed to Dearie. But given Dearie’s evenhandedness thus far, Trump and his team may regret asking for a special master.

Again, Dearie held his hearing the day before the 11th Circuit denied Trump access to documents the FBI obtained at Mar-a-Lago that were marked as classified and allowed the DOJ to continue to use those documents in its investigation.

Out of court, Trump has claimed that he properly had possession of many of the documents the FBI found because he had declassified them. But in court filings, Trump’s team has been careful to only say Trump had the power to declassify documents, not that he actually did declassify the documents. In Dearie’s court Tuesday, Trump’s legal team refused to provide any evidence that Trump declassified any of these documents. This prompted Dearie’s now-viral comment, “You can’t have your cake and eat it too.”

Of course, even if Trump did declassify these documents, that would not necessarily save him from criminal liability if the Justice Department pursued charges against him. Some documents must be properly stored and handled, even if they have been declassified.

Dearie’s order can best be described as a “put up or shut up” moment for Trump and his team.

Out of court, meaning not under oath, Trump has claimed the FBI might have planted the documents left at his house. Dearie ordered Trump’s legal team to state in a court filing, meaning under penalty of perjury, whether the legal team thinks FBI agents lied about the documents that were obtained at Mar-a-Lago. Dearie’s order can best be described as a “put up or shut up” moment for Trump and his team.

It’s hard to rate which legal news was worse for Trump last week. But one big takeaway is that contrary to how Trump might have expected them to behave, judges he or other Republicans appointed aren’t leaping to take his side. Instead, in two different courtrooms, Republican-appointed judges handed Trump big legal setbacks. The 11th Circuit corrected part of Cannon’s erroneous legal ruling and allowed the DOJ to use the documents marked as classified in its investigation. Dearie sharply questioned Trump’s legal team and fairly handled the case. These are judges following the rule of law. Given Trump’s frivolous claims, this is bad for him.

Let’s not kid ourselves. Sometimes it matters whether or not a judge was appointed by a Republican president or a Democratic president. And our suspicions of judges as partisan actors is validated. But not always, and not in every case. Last week was a good reminder of that fact.