Trump’s Court Victory Is More Dangerous Than It Looks

Trump’s Court Victory Is More Dangerous Than It Looks

Ankush Khardori — Read time: 12 minutes

On Monday, Donald Trump got a significant legal victory in the wake of the search of his Mar-a-Lago home last month as part of the Justice Department’s investigation concerning his potentially unlawful retention of sensitive government documents. Federal district court judge Aileen Cannon, a Trump appointee who was confirmed by the Senate shortly after Trump lost the 2020 election, issued a decision granting Trump’s request for an independent third party known as a special master to review the evidence taken and temporarily prohibiting the department from “using the seized materials for investigative purposes.”

The decision is not exactly surprising, since Cannon had explicitly said more than a week before her ruling — before she had even heard the Justice Department’s position — that she was inclined to grant Trump’s request. The ruling may have been expected, but it was still largely specious. I say “largely” because some of the arguments that the government advanced — that Trump had no standing even to go to court or perhaps had waited too long to do so — were in fact very dubious. Still, the ruling likely came as a shock to many people, since quite a few legal observers have been claiming that a criminal case against Trump is a slam dunk — that it would be “relatively easy” for prosecutors to charge Trump; in fact, so easy that pleading guilty “may be the best move Trump has left.” Cannon’s decision is yet another reminder that confidently predicting the trajectory of a Trump investigation can be a perilous business.

On the core issues, however, the judge adopted the most Trump-friendly reading of the law and the facts. Most notably, the ruling provides for a special-master review that would include Trump’s claims of “executive privilege,” but as many people have noted by now, it is far from clear how a special master should adjudicate a dispute between the current and former presidents on this subject, which happens to be a notoriously murky and unsettled area of the law. Cannon largely ignored these legal and practical difficulties, which are likely to be a major source of contention between the parties if the special-master process goes forward and even if the Justice Department decides not to immediately appeal Monday’s decision.

The quality of the opinion’s analysis on narrower and more discrete points is extremely questionable. Cannon placed great weight, for instance, on the fact that the government apparently obtained some “medical documents, correspondence related to taxes, and accounting information” in the course of the search, but by itself, that fact is not particularly surprising. After all, the investigation concerns whether Trump improperly retained government documents by unlawfully treating them like his personal effects and whether he lied to cover it up. Under the circumstances, any competent prosecutor — for what it’s worth, Cannon is a former prosecutor — would have to at least wonder whether Trump and his team deliberately intermingled the government documents among his personal belongings in order to make them harder for the Justice Department to locate and recover in a search.

The judge found that Trump would incur a “risk of irreparable injury” without a special master, but if you took Trump’s status as a former president out of the equation, none of the judge’s conclusions on this point make much sense. She concluded that Trump would be “deprived of potentially significant personal documents,” but there was no showing by Trump’s lawyers of any real risk on this front; it’s not even clear that these were the only copies of the relevant documents. Cannon expressed concern over an “unquantifiable potential harm” that might result from leaks to the media about those “potentially significant personal documents” even though there do not appear to have been any such leaks in the weeks since the search. She argued that Trump might suffer “from the threat of future prosecution and the serious, often indelible stigma associated therewith” if he’s ultimately charged but not convicted — a risk faced by literally every person whose conduct is under criminal investigation but one that Cannon put “in a league of its own” for Trump given his status as a former president.

The ruling may seem modest in effect, and depending on how things unfold, it may turn out to be, but it introduces a bunch of avenues for Trump and his lawyers to exploit for delay or to otherwise complicate the government’s investigation. They include lobbying the court for a favorable special-master-review protocol (one, for instance, that might give the Trump lawyers access to everything that was taken), going to the court to complain that the investigation team has been improperly “tainted” by inadvertently reviewing potentially privileged materials and that lawyers on the case should therefore be removed (the judge alluded to this possibility in a footnote in her ruling), and advancing an aggressive position on executive privilege with the special master that could result in a dispute that needs to be resolved by appeals courts — including the Supreme Court.

The opinion seems oblivious (intentionally or otherwise) to how the Justice Department typically conducts “filter reviews,” which are common when the government believes that it may have come into possession of material that is subject to attorney-client privilege. Generally speaking, a separate team of prosecutors reviews what was seized and filters out potentially privileged material so that this information is not available to the prosecutors and agents working on the investigation. The ruling suggests, for instance, that the government’s filter team might be systematically biased in favor of the government, but in fact, everyone’s rational incentive is for the government’s team to be extremely conservative in making privilege determinations, because the risk of a so-called taint, even accidentally, can become a huge problem if the subject of the search is later charged.

I had the misfortune as a prosecutor of being on both sides of this process, and it was not pleasant. When I had to serve as a filter attorney, I used a very generous standard for withholding potentially privileged material from members of the investigative team, because I did not want them to incur even the remote risk of a taint. I was also the lead prosecutor in a case that had a real taint issue due to the inadvertent error of a colleague, and it was miserable. I lived in fear that the whole case might be dismissed.

The point here is not that the government’s internal processes in a criminal investigation are infallible. They can and do occasionally fail, and the concept of a government-run filter review is something that many defense lawyers see as close to an oxymoron. These risks, however, are present in every investigation, and in the vast majority of cases, the subjects and potential targets are powerless to do anything about them unless and until someone is actually charged — at which point there is a well developed body of law concerning the suppression of evidence and other legal remedies for significant missteps by the government.

Much of Cannon’s opinion has this problem: treating commonplace features of federal criminal investigations as somehow unusual or questionable simply because they concern Trump. The decision tries to put the best face on the result by arguing that a special master will bolster public confidence in the investigation, but even if that’s true, it is hard to believe that any other subject of a criminal investigation would’ve been treated with as much solicitude and deference as Trump was.

Of course, one near-term question for the Justice Department is whether to appeal the ruling. There is a good case to be made that it should, simply because the ruling is so bad on the merits of the key legal questions, but it would go to the relatively conservative 11th Circuit Court of Appeals. This is the same court that just stepped in to help Lindsey Graham in his effort to avoid testifying in the criminal investigation concerning Trump conducted by Atlanta’s District Attorney, so the government’s odds of success on appeal are far from certain.

Even if the government did manage to prevail on appeal, Trump’s lawyers would presumably try to take it to the Supreme Court, where a conservative majority that includes three Trump appointees could make things even worse for the Justice Department in ways that cannot be fully predicted. As a result, there is a plausible case for the Justice Department to simply stay the course and hope for the best with a special master as it navigates an unprecedented process before a Trump-friendly judge. It’s a predicament with no self-evidently correct answer.

Since the release of Cannon’s opinion on Monday, there has already been some commentary about how the ruling could be used as precedent by defendants in other criminal cases in order to get the same sort of preferential treatment and relief that Trump just obtained. The concern is not entirely misplaced, because if Monday’s ruling actually became the norm in other cases, it would wreak considerable havoc on the Justice Department’s work by providing the subjects and potential targets of criminal investigations with the ability to temporarily stop the government’s work any time they can come up with some claim that the government has obtained potentially privileged information.

In a perverse way, however, these worries might turn out to be overly optimistic. That is because they assume that the opinion is now “law” in a conventional sense — a ruling that is available to any other litigant, regardless of who they are and what they may have done, to try to leverage in their favor in order to change the course of a legal proceeding.

We may instead be seeing the development of a new body of Trump-specific law in this strange nether region between “law” and “politics.” Indeed, the ruling on Monday has the hallmarks of some of the country’s most controversial legal fights — like the Supreme Court’s decision in Bush v. Gore or the Guantanamo detainee cases. These decisions are on the books as “law” even though the identities of the litigants were inextricably tied to the results — in the former case, because a conservative majority of the Supreme Court wanted George W. Bush to be president instead of Al Gore, and in the latter case, because the detainees were accused terrorists.

You might agree or disagree with the specific results, but in practice, the decisions do not operate like generally applicable rulings from which judges and litigants can extract principles that might be relevant to their cases. They exist as widely recognized, extremely context-specific rulings that are pretty much useless in any other setting.

The decision on Monday is a significant victory for Trump that creates real risks and land mines for the Justice Department that are impossible to fully game out. There is no way to predict how this will all end, but for the first time since the search of Mar-a-Lago, Trump and his lawyers should be feeling pretty good.