Donald Trump Has a Fresh Legal Headache and It May Be His Worst Yet

White House chief of staff Mark Meadows listens as Donald Trump speaks to the press outside the White House on Oct. 30, 2020. Sarah Silbiger/Getty Images

Former President Donald Trump once promised that under him, his supporters would “get tired of winning.” He must not have been talking about in the courtroom. On Friday it was reported that Trump has suffered yet another devastating judicial defeat in his campaign to thwart the various criminal investigations targeting him. D.C. District Court Judge Beryl Howell rejected his claim of executive privilege to stop his former chief of staff Mark Meadows and other top aides from testifying in Special Counsel Jack Smith’s Jan. 6 probe.

Indeed, it may be the costliest moment yet in Trump’s long losing streak against Smith, greatly increasing the odds of federal charges against the former president.

Meadows’ testimony matters enormously. He was one of the few staffers in continuous contact with Trump on Jan. 6 as the siege occurred. And in the weeks leading up to Jan. 6, according to NPR, Meadows was also “at the very center of Trump’s plans to overturn his presidential election” loss.

For example, Meadows traveled to Georgia seemingly on Trump’s behalf on December 22, 2020, and was apparently involved in setting up Trump’s call the following day to the state’s chief elections investigator, Francis Watson. That call was tape recorded, as was Trump’s infamous January 2, 2021 phone call to Brad Raffensperger, Georgia’s secretary of state, in which Meadows participated. (Fulton County, Georgia, District Attorney Fani Willis is also investigating those events.)

Meadows also has vital testimony about Jan. 6 itself. Evidence the House Jan. 6 committee gathered showed that he had advance intelligence about the coming violence. If so, Smith will want to know about any discussion with Trump about those early warnings.

Likewise, Smith will surely seek Meadows’ testimony about a damning conversation to which Cassidy Hutchinson, Meadows’ aide, testified in Congress. She said Meadows told her that Trump, upon hearing that the insurrectionists were screaming “Hang Mike Pence!,” replied that Pence “deserved it.”

In addition, Meadows withheld about 1,000 text messages subpoenaed by the Jan. 6 committee, after providing more than 2,300 others. The committee has shared the documents it received with the special counsel, and he will certainly want those additional withheld messages, along with Meadows’s testimony about them. (Meadows refused to testify before the Jan. 6 committee, making an executive privilege claim similar to the one that has now been rejected in court.)

As for Judge Howell’s ruling that Meadows and the others must testify, we don’t know her exact reasoning because her ruling is under seal. But we do know its foundations.

In a 1977 case involving former President Richard Nixon after he’d left the White House, the Supreme Court said the incumbent president who succeeded him was “in the best position to assess the present and future needs of the Executive Branch” in deciding whether the privilege applies. Trump’s successor, President Joe Biden, has consistently declined to support Trump’s privilege claims around Jan. 6.

In January 2022, the Supreme Court rejected those claims when Trump unsuccessfully sought to block release of White House documents to the Jan. 6 committee.

In another Supreme Court decision involving Nixon, 1974’s celebrated “White House tapes” case, the court held that “the President’s generalized assertion of privilege must yield to the demonstrated, specific need for evidence in a pending criminal trial.”

Although this criminal trial isn’t yet “pending,” we have that specific need here in spades. Indeed, another federal judge found Trump “more likely than not” conspired to defraud the United States in connection with the effort to persuade then-Vice President Mike Pence to reject certain states’ electoral votes, and also conspired to obstruct Congress on Jan. 6. Then there are the crimes for which the Jan. 6 committee issued criminal referrals to the Justice Department, such as inciting, assisting, and giving aid or comfort to insurrectionists.

Trump is expected to appeal, as usual. Though his prospects are dismal given the precedents, appeals can take time.

Then again, it took less than a day for the U.S. Court of Appeals for the District of Columbia Circuit this month to reject another Trump appeal to keep his lawyer, Evan Corcoran, from providing evidence about Smith’s Mar-a-Lago documents investigation. It seems clear that judges are losing patience with the former president’s dilatory litigation tactics.

At any rate, Smith’s focus on Meadows suggests the special counsel is preparing his endgame. In conspiracy cases, prosecutors proceed first to gather evidence from the least culpable witnesses and last to gather evidence from those who are most culpable and closest to the investigation’s target.

As for Meadows’s endgame, with executive privilege off the table, his most likely recourse to block questioning will be the Fifth Amendment. Based on what we know from the Jan. 6 committee’s extensive public record, Meadows has serious criminal exposure of his own.

If Meadows invokes his right to remain silent, the Justice Department will decide whether to compel his testimony by granting him immunity. Such grants eliminate a witness’s criminal exposure and therefore his right to remain silent.

Whatever Smith decides, he now has the upper hand. He has shown that he picks his battles smartly, starting only the fights in which he is confident he can prevail. The special counsel has apparently not gotten tired of winning in his relentless investigations of Donald J. Trump.