This image contained in a court filing by the Department of Justice on Aug. 30, 2022, and redacted by in part by the FBI, shows a photo of documents seized during the Aug. 8 search by the FBI of former President Donald Trump's Mar-a-Lago estate in Florida.
CNN  — 

A federal judge in Florida dealt the Justice Department another setback in its investigation into the handling of documents from former President Donald Trump’s White House with a trio of orders Thursday night.

US District Judge Aileen Cannon appointed Raymond Dearie, a Brooklyn based senior federal judge, to be the special master to review the materials that were seized. In an order setting the parameters of the review, she mostly sided with Trump’s proposals for the shape it could take, creating a much slower and extensive process than what the prosecutors had recommended.

In what was perhaps the biggest shot at the Justice Department, she also denied its request that the documents it seized that were marked as classified be carved out from the review, keeping in place her order blocking the criminal investigation from using them.

That move by Cannon sets the stage for the Justice Department to quickly put the dispute over the materials in front of an appeals court and perhaps even the Supreme Court in the coming days.

Here’s what happens next:

An appeal could come instantly, and this could eventually reach the Supreme Court

When the Justice Department asked Cannon to resume the criminal probe’s review of the classified documents, it told her that, if she didn’t act by Thursday, the prosecutors would seek the intervention of an appeals court.

She met their deadline, but not with the answers they wanted. Her denial of the request all but guarantees the department will file an emergency request with the 11th US Circuit Court of Appeals as soon as Friday.

Though the government had already filed a separate notice of appeal of her previous order granting Trump’s request for special master, that appeal will move at a much slower pace than the expected higher court litigation over the Mar-a-Lago documents identified as classified.

Trump appointees make up six of the 11 active judges on the 11th Circuit, where the case will head next. If the Justice Department asks the circuit court to quickly step in, it will go to a panel of three randomly selected judges from the court. It’s worth noting that Cannon, also a Trump nominee, has shown skepticism toward some of the Justice Department’s arguments. That’s outside the norm for even many fellow Republican-appointees, so a panel with GOP-picked judges doesn’t necessarily mean the Justice Department’s case is doomed.

From the 11th Circuit, the next stop would be the US Supreme Court, which previously rejected Trump’s arguments for why documents from his White House should be withheld from House January 6, 2021, investigators.

The criminal probe, for now, has major limits on what it can do

For as long as the special master process is ongoing, the Justice Department criminal investigation will not be able to use the documents it seized at Mar-a-Lago last month. Cannon’s order Thursday made clear that that also meant that the seized materials could not be presented to a grand jury or used in witness interviews.

She did specify, however, that aspects of the criminal probe that do not rely on the seized documents can continue and that investigators can gather information about how the documents were generally stored and moved.

Special master review stretches into the holidays

The special master review, if it continues forward uninterrupted, will likely stretch past the midterm elections and into the holidays.

By September 25, the special master will have to advise Cannon of the timelines for DOJ and Trump’s lawyers to work through the documents.

Cannon ordered the special master to aim to finish by November 30. That’s about a month and a half longer than what the DOJ had hoped for, but slightly quicker than Trump’s team suggested.

Trump however, will have to cover the costs of the entire special master review, Cannon ruled.

A blurry outlook for how the intelligence community’s assessment is to proceed

Cannon roundly rejected the Justice Department’s arguments that her order blocking the use of the classified documents in the criminal probe was hindering an intelligence community assessment of the documents – which she said could continue – to the point that the intelligence assessment was now on pause.

The Justice Department had argued the intelligence community review and criminal investigations cannot be separated.

But, confusingly, Cannon also said that the government could take the sort of criminal investigatory steps she had barred if those steps were necessary and inextricable from the intelligence community assessment.

Cannon didn’t explain scenarios where such investigative moves would be acceptable, saying only in a footnote that she was “confident that the Government will faithfully adhere to a proper understanding of the term ‘inextricable’ and, where possible, minimize the use and disclosure of the seized materials in accordance with the Court’s orders.”

The lack of clarity could be one of the issues the Justice Department raises to the 11th Circuit if and when it asks the appeals court to step in.

Trump gets ability to try to block and tackle

Trump’s lawyers will also be able to look at all the documents – including ones marked as classified – that are currently in the hands of prosecutors.

Those defense lawyers will then get to work, classifying documents as personal or presidential records, and deciding which in each category they want to try to keep from investigators by claiming executive privilege.

The special master comes in next, asking the Justice Department for its say on each document. Dearie will take in the DOJ’s and the Trump team’s respective decisions if the two sides disagree, then make his own calls, to be signed off or rejected by Cannon.

Dearie will also be reconciling what to do with documents the Justice Department’s own filter team has separated as potentially needing to stay private.

The document-by-document approach will pick through all the evidence seized from Mar-a-Lago before it can be used in the DOJ’s criminal investigation. And that could take months.

While the special counsel will aim to wrap his reporting to the judge by December, the process could go on longer if Cannon has to settle prolonged standoffs. Trump’s lawyers and the Justice Department will have opportunities to object to what Dearie decides on each document, potentially putting some decisions privilege ultimately in the judge’s hands.