Judge Cannon adds new wrinkle to Trump’s classified docs case

When we last looked at Donald Trump’s classified documents case, I noted that the plot was thickening in Florida, with special counsel Jack Smith raising a conflict-of-interest issue for Trump co-defendant Walt Nauta’s lawyer. On Monday, Judge Aileen Cannon’s response to Smith’s request for a hearing on the conflict issue thickened the plot even further, with the Trump-appointed judge raising questions about the case itself.

In doing so, Cannon added a wrinkle that could lay the groundwork for an outlandish ruling that throws a wrench into one of Trump’s two federal prosecutions — or she could just be putting the government through its paces, in making the Justice Department explain why its investigative actions have been appropriate to date.

Here’s what happened and what it could mean — the short answer is it could amount to nothing besides additional litigation on an unnecessary issue, which, given the delay theme animating all of Trump’s current cases, is more than nothing.

But first, a quick refresher on how we got here. In filing the conflict motion last week, Smith’s team raised concerns about Nauta lawyer Stanley Woodward having represented — both currently and previously — possible trial witnesses against Nauta.

Among the people Woodward represented was Yuscil Taveras; according to the government’s motion, when Woodward still represented Taveras before Trump and Nauta were first indicted on June 8, Woodward said he was unaware of testimony Taveras could give against Nauta. But after Trump and Nauta’s initial indictment, Taveras obtained new counsel in early July and, later that month, a superseding indictment charged Trump, Nauta and new defendant Carlos De Oliveira with, among other things, asking Taveras to delete security footage at Trump’s Mar-a-Lago property to prevent the grand jury from seeing it.

Now prosecutors want Cannon to hold a hearing on the potential conflict posed by Woodward’s representation of both Nauta and possible witnesses against him, including Taveras. In support of their motion, prosecutors noted that after the initial June 8 indictment, grand juries in both Florida and Washington, D.C., continued to investigate “further obstructive activity,” leading to the July 27 superseding indictment. In support of their requested hearing, prosecutors also filed information under seal with Cannon, opting not to submit it publicly in order to comply with what they deemed grand jury secrecy.

But on Monday, Cannon didn’t just strike the government’s sealed filings for failing, in her view, to provide sufficient basis for secrecy. In a move that raises additional questions, the judge’s order also said Nauta’s response to the conflict-of-interest hearing motion “shall address the legal propriety of using an out-of-district grand jury proceeding to continue to investigate and/or to seek post-indictment hearings on matters pertinent to the instant indicted matter in this district.”

So, what does that mean and what are its implications for the case?

While it’s not 100% clear what Cannon has in mind, she might be referring to the notion that prosecutors can’t just use grand juries to keep building their case against a defendant who has already been indicted. Though that doesn’t seem to be what happened here, necessarily — federal prosecutors obtained a superseding indictment that also included a new defendant — Cannon could be probing the limits of how prosecutors can use grand juries after an indictment.

Of course, that opens a range of possibilities once she effectively starts calling the current indictment into question — none of them great for the special counsel.

But if Cannon uses the grand jury issue to render an outlandish ruling like the ones of hers that were reversed during the search warrant litigation before Trump was charged, then that could finally raise a real prospect for the Justice Department to try and kick her off the case. At this point, such an attempt would still be premature, but it’s reasonable — especially given Cannon’s history — to keep a watchful eye on this latest litigation.

Whatever the judge has in mind, the likely function of her order for now will be to serve as a defense invitation to broadly attack the case. Nauta’s motion is due by Aug. 17. Cannon invited the other defendants — Trump and De Oliveira — to weigh in as well, also by Aug. 17, whether jointly or separately, on “the grand jury issue.”   

With the special counsel’s reply due by Aug. 22, we should hopefully have a better idea of what Cannon has in mind later this month — and what it means for the classified documents case.