On Jan. 20, Trump will lose a major perk. Here's what legal challenges await him.

Tom Winter
·8 min read

It looks increasingly certain that on Jan. 20, 2021, around noon, Joe Biden will take the oath of office as president, and Donald Trump will lose both his job and one of its most important perks.

Trump has faced investigations involving his campaign, his business, and his personal behavior since he took the oath of office himself four years ago. As soon as he becomes a private citizen, however, he will be stripped of the legal armor that has protected him from a host of pending court cases both civil and criminal.

He will no longer be able to argue in court that his position as the nation’s chief executive makes him immune to prosecution or protects him from turning over documents and other evidence. He will also lose the help of the Department of Justice in making those arguments.

While it is possible he could go to jail as a result of some of the probes of his business affairs, the soon-to-be-former president is more likely to face financial punishment in the form of civil fines, law enforcement observers believe. He may also be embarrassed by financial and other secrets that will be exposed in court. Nearly all his legal troubles are in his hometown of New York, where he once basked in the tabloid limelight as a young mogul and where he rode a golden escalator into an unlikely political career.—

Here are some of the most perilous cases that await President Trump when he’s no longer president — and here’s how he could yet use the powers of the nation’s highest office to escape punishment:

The Manhattan district attorney’s case

Former Trump lawyer Michael Cohen pleaded guilty in 2018 to campaign finance violations for paying porn star Stormy Daniels to keep silent about her alleged affair with Trump. The indictment alleged Cohen had paid Daniels $130,000 prior to the 2016 election for the benefit of “Individual-1,” an unindicted coconspirator described as an “ultimately successful candidate for president.” But federal prosecutors in the Southern District of New York didn't seek charges against Trump, who would have been immune from prosecution regardless while president.

Image: Donald Trump, Michael Cohen, Trump appears with Cohen during campaign stop at the New Spirit Revival Center church in Cleveland Heights, Ohio (Jonathan Ernst / Reuters file)
Image: Donald Trump, Michael Cohen, Trump appears with Cohen during campaign stop at the New Spirit Revival Center church in Cleveland Heights, Ohio (Jonathan Ernst / Reuters file)

Two prosecutors in New York seem to have picked up where federal prosecutors left off in examining Trump finances.

Manhattan District Attorney Cy Vance is probing a variety of alleged financial improprieties. Court documents show that the DA is investigating “possibly extensive and protracted criminal conduct at the Trump Organization,” the president’s family business, which could include falsifying business records, insurance fraud and tax fraud.

While the campaign finance violation of Individual-1 is not a federal case, New York state law says that falsifying business records in furtherance of an illegal act is a felony. Cohen has also alleged that Trump effectively uses two sets of numbers in his business, one with higher values to secure loans, and a second with lower values to minimize taxes, according to his congressional testimony and published interviews. While Trump has declined to release his tax returns, saying he is under audit, the New York Times has obtained many years of his tax records, and determined that he had paid no federal income tax for 10 of the years and $750 in each of two other years.

Image: Stormy Daniels speaks to members of the media outside U.S. Federal Court (Hector Retamal / AFP - Getty Images file)
Image: Stormy Daniels speaks to members of the media outside U.S. Federal Court (Hector Retamal / AFP - Getty Images file)

Vance’s office has subpoenaed eight years of the president’s tax documents from his tax preparer, Mazars USA LLC, a subpoena the president fought all the way to the highest court in the land. The Supreme Court ruled in October 2019 that Trump was not immune from having to provide those documents while president and could only fight the subpoena along the same grounds that any other person could, on the merits.

Since that ruling, the president’s legal team has fought the subpoena on its merits, but has lost in the district and appellate courts. The Supreme Court must now decide whether to accept the president’s emergency request for a stay of the lower courts’ rulings and possibly hear the case again, or deny that stay. It's unknown when the Supreme Court could announce a decision, which would be made by a high court that now includes three Trump appointees.

If the stay request is denied, Vance gets the documents as soon as Mazars can transfer the files. This is the only known criminal investigation involving Trump, and if convicted the penalties could be solely or largely financial.

NBC News legal analyst Danny Cevallos said he expects Vance to pick the “lowest hanging fruit” of crimes to charge, which would likely be tax evasion or falsifying business records.

The penalty for falsifying business records can be up to a year in prison with fines or probation with fines.

Cevallos said a person can be found guilty of falsifying business records in the second degree in New York “when he has the specific intent to defraud. That means that he intends to cheat or deprive another person of property or a thing of value.”

He said a lower level employee could claim he or she didn’t personally benefit from the crime or merely executed orders on someone’s behalf. That affirmative defense likely wouldn’t apply to Trump.

The New York attorney general’s case

The office of New York Attorney General Letitia James, meanwhile, is investigating four different Trump Organization real estate projects and the failed attempt to purchase the NFL’s Buffalo Bills. In March 2019, the office subpoenaed records from Deutsche Bank and Investors Bank. The fraud probe was reportedly prompted by Cohen’s testimony before Congress that he had inflated his financial assets.

The attorney general’s investigation is civil, not criminal, but the office would be allowed to refer any allegedly criminal elements to local prosecutors like Vance.

The Trump properties that James's office is investigating, according to court filings, include the Seven Springs Estate, a 212-acre property just north of New York City that the company is seeking to develop; 40 Wall Street, a heavily leveraged building owned by the company in Lower Manhattan; Trump International Hotel and Tower Chicago; and Trump National Golf Club Los Angeles.

Trump has blasted both the Vance and James probes as politically motivated.

The women

Multiple women have accused Trump of inappropriate sexual behavior in alleged incidents that date as far back as the 1970s. Trump has denied the allegations. A few of the women have taken legal action, and in the case with the most serious potential implications, Trump enlisted the Department of Justice as his attorney to prevent submitting evidence.

Advice columnist E. Jean Carroll alleged in a 2019 book that more than 20 years earlier, Trump raped her in a department store dressing room. Trump denied the allegation, saying she was not his type, and that the claim was meant to spur publicity for her book of “fiction.” Carroll sued saying the president had defamed her by accusing her of lying.

The Justice Department moved the case from state to federal court, and also filed a motion to act as the president’s defense attorney, saying that his denial of her rape allegation was a presidential act.

A judge denied the Justice Department’s motion in late October. As a private citizen and a defendant in a civil suit, Trump may now be compelled to provide evidence in the case — meaning testimony and, potentially, a DNA sample.

Summer Zervos, a former contestant on The Apprentice, has also filed a defamation suit against Trump for denying her accusations of sexual assault. In a suit filed in early 2017, Zervos said he grabbed her breast and kissed her without permission. Trump agreed to testify, but his lawyers were able to postpone that testimony pending a decision from the New York State Court of Appeals that is not expected until next year.

E. Jean Carroll at her home in Warwick, N.Y. (Eva Deitch / The Washington Post/Getty Images)
E. Jean Carroll at her home in Warwick, N.Y. (Eva Deitch / The Washington Post/Getty Images)

Could Trump pardon himself before Jan. 20?

Legal experts said the president could pardon himself before leaving office, but it's unlikely such an action would survive a challenge in court.

“Could I say that I’m the starting center fielder for the Washington Nationals? You bet I can,” said NBC News legal analyst Chuck Rosenberg, a former FBI official and U.S. attorney. “Does it make a damn bit of difference to the Washington Nationals? No.”

The Justice Department tackled this very issue on Aug. 5, 1974 — four days before Richard Nixon resigned as president.

In a memo written by an acting assistant attorney general, the Justice Department determined that “under the fundamental rule that no one may be a judge in his own case, the President cannot pardon himself.”

The Justice Department opinion has never been tested in court. After succeeding Nixon as president, Gerald Ford gave him a "full, free, and absolute pardon" for any crimes he may have committed.

The 1974 memo does lay out one scenario for a self-pardon that experts have described as far-fetched and worthy of Hollywood. Says the memo, “If under the Twenty-Fifth Amendment the president declared that he was temporarily unable to perform the duties of the office, the vice president would become acting president and as such could pardon the president.

“Thereafter the president could either resign or resume the duties of his office.”

Any presidential pardon, whether bestowed by Acting President Mike Pence or by Trump himself, would only cover federal crimes, which would not help Trump in his New York state cases.