Jack Smith, left, and Donald Trump
CNN  — 

Special counsel Jack Smith is locked in at least eight secret court battles that aim to unearth some of the most closely held details about Donald Trump’s actions after the 2020 election and handling of classified material, according to sources and court records reviewed by CNN.

The outcome of these disputes could have far-reaching implications, as they revolve around a 2024 presidential candidate and could lead courts to shape the law around the presidency, separation of powers and attorney-client confidentiality in ways they’ve never done before.

Yet almost all of the proceedings are sealed, and filings and decisions aren’t public.

The sheer number of grand jury challenges from potential witnesses is both a reflection of the scope of the special counsel’s investigation and a hallmark of Trump’s ultra-combative style in the face of investigations.

By comparison, Robert Mueller’s grand jury investigation into Trump had a smattering of sealed proceedings where investigators used the court to pry for more answers, and independent counsel Kenneth Starr’s Whitewater investigation ultimately totaled seven similar sealed cases.

A key sealed case revealed Wednesday is an attempt to force more answers about direct conversations between Trump and his defense attorney Evan Corcoran, where the Justice Department is arguing the investigation found evidence the conversations may be part of furthering or covering up a crime related to the Mar-a-Lago document boxes.

A spokesman for Smith’s office declined to comment.

About half a dozen cases are still ongoing in court, either before Chief Judge Beryl Howell or in the appeals court above her, the DC Circuit. Most appear to follow the typical arc of miscellaneous cases that arise during grand jury investigations, where prosecutors sometimes use the court to enforce their subpoenas.

More challenges from subpoenaed witnesses – including former Vice President Mike Pence – are expected to be filed in the coming days, likely under seal as well. Pence may raise novel questions about the protections around the vice presidency.

Investigations that implicate government officials often beget sealed court proceedings, because confidential grand jury witnesses become more likely to assert privileges that prompt prosecutors to ask judges to compel more answers, criminal law experts say.

“I think we are in extraordinary times. Part of it is I think President Trump continues to assert these theories long after they’ve been batted away by the court,” Neil Eggleston, a former White House counsel who argued for executive privilege during the Clinton administration and the Whitewater investigation.

In Whitewater, after the court in DC ruled that privilege claims wouldn’t hold up when a federal grand jury needed information, other witnesses shied away from trying to refuse to testify, Eggleston recalled. But in the Trump investigations, witnesses aligned continue to test whether he still may have special confidentiality protections.

Still, the number of cases is out of the ordinary.

The other known cases are:

The Justice Department’s long-running effort to enforce a May 2022 subpoena for all classified records in Trump’s possession. After a sealed December hearing, Howell gave Smith’s investigators an avenue to ask more questions of two people hired to search Trump’s properties in December and found more documents with classified markings. Those two people testified to the grand jury late last month. Sixteen national media outlets, including CNN, have asked Howell to make public transcripts of hearings and other records in the case.

An appeal over whether former Pence chief counsel Greg Jacob and chief of staff Marc Short should have been forced to answer questions about Trump interactions around January 6. Both went to the grand jury in DC on the same Friday last July and refused to give some answers because of Trump’s attempted claims of confidentiality around the presidency. Court orders prompted them to testify a second time, seeking out more testimony from them in October last year, CNN previously confirmed. They both appeared a second time at the grand jury. The Trump team still has filed an appeal of Howell’s decisions.

An appeal over whether former Trump White House counsel Pat Cipollone and deputy White House counsel Patrick Philbin could decline to answer questions about direct conversations with Trump from the end of his presidency. Both men cited various privileges when they testified to the grand jury in September, but were forced to appear a second time and give more answers after court rulings in November and December, CNN previously confirmed. Though they have already testified twice, Trump’s team filed an appeal.

Following the seizure of Pennsylvania GOP Rep. Scott Perry’s cell phone in August in the January 6 investigation, lawyers for the congressman challenged the Justice Department’s ability to access data taken from the phone, citing protection around Congress under the Constitution’s Speech or Debate Clause. Howell refused to keep the records from investigators, but an appeals court panel has blocked the DOJ from seeing the records so far, according to indications in the court record. The case is set for oral arguments on February 23 at the appeals court in Washington. The circuit court also has a request from the Reporters Committee for Freedom of the Press to unseal documents in the case.

Both Republican and Democratic leadership in the US House have wanted a part in the case because of the implications for Congress, CNN has confirmed.

Howell has released redacted versions of two attorney confidentiality decisions she made last year giving prosecutors access to emails between Perry and three lawyers – John Eastman, Jeffrey Clark and Ken Klukowski – before January 6, 2021.

Howell separately denied Clark’s attempt to keep from investigators a draft of his autobiography that discussed his efforts at the Justice Department on behalf of Trump before January 6. Clark had tried to mark the draft outline about his life as an attorney work product.

The Justice Department secured a court order for Trump adviser Kash Patel to answer questions under oath in the Mar-a-Lago investigation. Patel initially declined to answer questions before the grand jury in October, citing his Fifth Amendment protection against self-incrimination. Then prosecutors fought for more answers by immunizing his testimony from prosecution, CNN previously reported.

Transparency is lacking

The suite of special counsel’s office grand jury cases raises questions how transparent the courts will be regarding these cases, and how soon documents filed in court could become available.

The New York Times and Politico are trying to convince Howell to release redacted versions of any sealed court fights related to the grand jury where Trump or others in his administration have tried to limit the investigation with claims of executive privilege, according to court filings.

The media organizations argue there’s a “profound national interest” in those legal papers.

But the Justice Department is against making disclosures related to the grand jury investigations – and won’t even admit the proceedings are taking place.

On Monday, they argued to Howell that with the intense public interest around the cases, there should be even more secrecy than when the court releases other records.

“To advance the policy goals underlying grand jury secrecy, it may well be necessary for a court to more frequently decline to release judicial opinions ancillary to grand jury investigations that are the subject of intense press attention as opposed to matters that have attracted little public attention,” lawyers from the DOJ’s civil division wrote.

Howell is still deciding what to do.