Trump Scoreboard: Toting Up the Legal Jeopardy


Image by Ray Shrewsberry from Pixabay

Will they finally nail him?  Ex-President Trump, that is.  He for whom an election is valid only if he wins.  He for whom taking the 5th indicates guilt unless he’s the one taking it.  

For those of us who don’t own MAGA hats, one of the additional good things about Donald Trump’s loss in the 2020 election was the sense that we no longer had to read about him, his rants, his shamelessness every day.  Wrong!  Our news was largely Trumpless for a while, but as the various investigations and perhaps prosecutions of him, his henchmen, and his company drag on, he’s seldom out of the headlines.

It’s hard to track the legal action without a scorecard.  And the scorecard changes almost daily.  The New York Times took a stab at it recently.  Here’s another attempt (mine) to make some sense of it all.


First and fundamentally, most of the allegations against Trump, his business, and his cronies, involve fraud:  financial fraud, which has caught the attention of New York’s attorney general and Manhattan’s district attorney; and political fraud – the pressure on state officials to falsify the vote, the recruitment of fake electors, or his telling the January 6 mob that the election had been stolen and encouraging the members to believe that Mike Pence (or someone else) had the legal power to toss out the popular vote. 

In addition to the frauds, you have what may or may not turn out to be an act of mindless kleptomania: taking a trove of official documents, some of them classified, down to Mar-a-Lago. 

The Insurrection of January 6

The Capitol attack on January 6 and the events leading up to it have starred in the main public spectacle, the House Select Committee’s hearings to Investigate the January 6 Attack on the United States. The committee has been laying out a quasi-legal case against Trump for the attack and the efforts – including that attack – to interfere with the certification of the election won by Joe Biden.  The Department of Justice (DOJ) has been gathering evidence – slowly, slowly, although the pace may be picking up now that it has issued roughly 40 subpoenas in a single week – and may or may not try to indict Trump, as it already has indicted lesser participants.


There seems little doubt that the Fulton County, Georgia, district attorney, Fani Willis, will try to indict him for his efforts to interfere with the election in Georgia.  Trump’s recorded pressuring of Georgia’s secretary of state, Brad Raffensperger, to “find” 11,780 votes, just enough to throw the election his way, certainly seems like a smoking gun.  It and the broader attempts there and elsewhere to create slates of fake electors, may eventually lead to federal charges. The action made public so far is Willis’ investigation and the closed-door testimony to a Fulton County grand jury.

Cooking the Books

Then, there are the strictly financial crimes: New York State attorney general, Letitia James, has just filed a $250 million civil suit against Trump, the Trump Organization, other business entities, his children Donald Jr., Ivanka and Eric, the Trump Organization’s former chief financial officer, Allen Weissellberg, and its controller, Jeffrey McConney. Both James and the Manhattan district attorney have been looking into the Trump Organization’s alleged practice of inflating property values to make the company’s assets look better when trying to borrow money or buy insurance, and deflating them when it’s time to pay taxes. Recall the Creedence Clearwater Revival verse in Fortunate Son:

   “Some folks are born silver spoon in hand
    Lord, don’t they help themselves, oh
   But when the taxman come to the door
   Lord, the house lookin’ like a rummage sale, yeah.”  

The Manhattan DA is pursuing a criminal case. 

Tax Scams

In addition to allegedly cooking the books on property values, the Trump Organization may face criminal charges for making non-cash payments to employees in order to lower their tax rates.  This and other alleged tax scams are more than plausible.  Let’s not forget that during a debate with Hillary Clinton during the 2016 election campaign, when Clinton said he hadn’t paid federal income taxes some years, Trump replied – in front of a national TV audience – that not paying taxes “makes me smart.”  

Purloined Documents

The most recent legal headline grabber has been Trump’s unauthorized removal to his Mar-a-Lago resort of government documents, some highly classified, and of empty folders that evidently once held highly classified documents.  A federal judge appointed by Trump, Aileen Cannon, has granted Trump’s request to appoint a special master to review all the documents.  FBI investigations were put on hold until the master finished his review. But now the 11th Circuit has   said the feds can go ahead and look at the roughly 100 classified documents found at the resort.


Trump has dismissed all of this as a political witch hunt.  It would be naive to assume and disingenuous to pretend that politics played no part.  With the notable exceptions of Liz Cheney and Adam Kinzinger the House committee looking into the Capitol attack is all Democrats.  The New York attorney general and Manhattan D.A. are Democrats.  So is the Fulton County prosecutor.  Would they be pursuing Trump and his enterprises so vigorously if they themselves were Republicans?  Of course not.  Which doesn’t mean they’re wrong.  And ultimately what happens may depend on judges and juries.

And, initially, it depends on U.S. Attorney General Merrick Garland.  Garland is, of course, part of a Democratic administration.  But he evidently: a)  wants to be impartial; b)  wants to look impartial; c)  wants to avoid any procedural missteps that could undercut a prosecution; d)  may or may not feel that the political damage done by prosecuting a former and perhaps future President would outweigh the political good.

Trump would not be the first ex-President to get a free ride.  President Gerald Ford famously pardoned Richard Nixon of Watergate and any other crimes committed during his term in office.  (Virtually no one realized that he should probably have been prosecuted for treason committed during his campaign for office.)  This pardon was controversial.  Ford wanted the country to move on.  It did, kinda.  But Nixon’s publicly-known crimes at the time pale beside Trump’s.  Prosecuting Trump would certainly inflame the enmity between his backers and detractors. Trump has said that if he’s indicted over the Mar-a-Lago papers, “I think you’d have problems in this country the likes of which perhaps we’ve never seen before.” But – let’s face it — not prosecuting him wouldn’t make the enmity go away.

Inciting a Riot

Despite the House committee’s piles of evidence, convicting Trump for inciting the riot may be a tough one.  The First Amendment protects most speech, even speech that advocates violence, unless there’s an immediate cause and effect.  The target must be right there.  The call to attack must be clear.  The Supreme Court said in Brandenberg that “the constitutional guarantees of free speech and free press do not permit a State to forbid or proscribe advocacy of the use of force or of law violation except where such advocacy is directed to inciting or producing imminent lawless action and is likely to incite or produce such action.” Trump clearly sent an armed mob to the Capitol to disrupt the counting of votes.  Did he intend what happened?  Well, he was in no hurry to stop it.  Is that enough to convict?  Probably not.

Firing up the mob that marched to and invaded the Capitol was clearly outrageous.  But did Trump incite the MAGA crazies to commit violence?  That’s a very high bar to clear.  On the other hand, did he conspire to interfere with a government function?  He probably did.  But then, he was the head of the executive branch of government at the time. Can he be charged with that particular crime?

One could argue it was perfectly OK – just an exercise of First Amendment rights to encourage a raucous demonstration at the Capitol. But perhaps one should draw a distinction between a legitimate effort to influence a political decision and an illegitimate effort to intimidate people carrying out a “ministerial” process – a prescribed process over which they have no discretion. Of course, part of the stop-the-steal shtick was the pretense that they did have discretion, but no even mildly objective authority thinks that was the case.

Justice Brandeis famously wrote in Schenck that “[t]he most stringent protection of free speech would not protect a man in falsely shouting fire in a theatre and causing a panic.” How about falsely telling an armed mob that an election had been stolen and partisans could make things right by marching right down the street to the nation’s Capitol?  And the mob did in fact march down the street to the Capitol?


Sending an armed mob down the street to influence a ministerial process isn’t politics.  It may be insurrection.  It almost certainly is conspiring to defraud the American government.  It no doubt is a lot of other things.  Is “insurrection” a stretch?  MAGA loyalists would certainly think so, but one could make a good case for insurrection. Some people who would like to see Trump barred from seeking office ever again hope someone will make that case.  U.S. law says anyone who “sets on foot, assists, or engages in any rebellion or insurrection against the authority of the United States or the laws thereof, or gives aid or comfort thereto” will not only face a fine or prison but “shall be incapable of holding any office under the United States.”  Charging Trump with that would be politically explosive, and the Justice Department probably won’t go that far. 

And yet, a judge in New Mexico has taken the leap:  New Mexico District Court Judge Francis J. Mathew unseated a county commissioner who had taken part in the Capitol attack, calling it an insurrection and saying that the insurrection included the “planning, mobilization and incitement” that led to the attack.  Mathew’s decision isn’t a precedent for anyone else, and it may not even survive an appeal, but it means that a charge of “insurrection” is no longer unthinkable.


Apart from insurrection or “solicitation to commit a crime of violence” (which targets anyone who “solicits, commands, induces, or otherwise endeavors to persuade such other person to engage in” a violent felony), what could Trump – and his cronies – be charged with?  One possibility might be conspiracy to defraud the United States. 

As the Department of Justice explains, “Section 371 [of title 18 of the U.S. Criminal code] reaches ‘any conspiracy for the purpose of impairing, obstructing or defeating the lawful function of any department of Government.’” The law “criminalizes any willful impairment of a legitimate function of government, whether or not the improper acts or objectives are criminal under another statute.”

DOJ also explains that key court “cases rely heavily on the definition of “defraud” provided by the Supreme Court in two early cases, Hass v. Henkel, 216 U.S. 462 (1910), and Hammerschmidt v. United States, 265 U.S. 182 (1924). In Hass the Court stated:

“‘The statute is broad enough in its terms to include any conspiracy for the purpose of impairing, obstructing or defeating the lawful function of any department of government . . . (A)ny conspiracy which is calculated to obstruct or impair its efficiency and destroy the value of its operation and reports as fair, impartial and reasonably accurate, would be to defraud the United States.’  

“In Hammerschmidt, Chief Justice Taft, defined ‘defraud’ as follows: ‘To conspire to defraud the United States . . . means to interfere with or obstruct one of its lawful governmental functions by deceit, craft or trickery, or at least by means that are dishonest.’”  All that’s needed is that the government’s “legitimate official action and purpose shall be defeated by misrepresentation, chicane or the overreaching of those charged with carrying out the governmental intention.”

Someone could certainly face charges for violating the prohibition against “Interference by administrative employees of Federal, State, or Territorial Governments.”  This section of the U.S. criminal code makes it a crime when anyone employed by the national government or any state “uses his official authority for the purpose of interfering with, or affecting, the nomination or the election of any candidate for the office of President, Vice President, Presidential elector, Member of the Senate, Member of the House of Representatives. . .”

Georgia, again

There are other possibilities: How about obstruction of justice?  And state law?  The Fulton County grand jury looking into Trump’s effort to flip Georgia’s election results can’t indict Trump.  But it can gather evidence that gives Prosecuting Attorney Fani Willis reason to indict him.  And possibly to indict Rudy Giuliani – who has been identified as a target – and other Trump cronies.  Willis has said publicly that those guys may go to jail. This won’t happen overnight.  The grand jury can meet until next spring.

Future Pardons

If Rudy and any other Trump cronies are charged with federal, as opposed to state, crimes, they can pray for Trump’s re-election. Trump served in Washington as the pardoner-in-chief and has said that if he’s re-elected, he may do it again, suggesting pardons for everyone convicted of crimes for their roles in the January 6 assault on the Capitol.

On the verge of leaving the White House, Trump pardoned his former strategist Steve Bannon who had faced federal charges of defrauding donors who had sent money to help build a border wall.  Now, Bannon faces New York State charges of money laundering, conspiracy, and scheming to defraud.  Trump had already pardoned his former campaign manager, Paul Manafort, his former adviser Roger Stone, and his son-in-law’s father, Charles Kushner.  Manafort had gone to prison for financial fraud and for conspiring to obstruct justice in the federal investigation of his acts.  Stone, whose prison sentence Trump had already commuted, had been convicted of lying to Congress about his approaches to Wikileaks, which released Hillary Clinton emails during the 2016 campaign.  Kushner had been convicted years earlier of charges that included tax evasion, campaign finance law violations, and witness tampering.

Pardons in New York State may be harder to come by – and there may be a market for them as Trump’s business, his colleagues including Donald Jr., Eric and Ivanka may all wind up facing criminal charges.

New York Case

New York AG Letitia James’ $250-million suit alleges multiple instances of fraud and misrepresentation. It alleges that Trump personally signed off on some of the false financial statements. (She had already argued in an earlier court filing that “[t]he knowledge and actions of Mr. Trump’s agents and attorneys can be imputed to Mr. Trump himself.”) Some of the allegations in the suit are complicated. Others are not. There’s nothing arcane about Trump claiming that his own apartment in Trump Tower measures 30,000 square feet when it actually measures 11,000. The document fills 280 pages. In addition to the money, James wants an order forbidding Trump and the Trump Organization from buying commercial real estate in New York or getting a loan from a New York-chartered company for five years, and permanently forbidding Donald Trump, Ivanka Trump, Donald Jr. and Eric Trump from serving as a director or trustee of any New York corporation. Weissellberg and McConney, would be barred from controlling the finances of any New York corporation.

Subpoenaed to testify, Trump took the Fifth Amendment 440 times.  His organization offered to settle. James rejected the offer. Then she sued. And she referred some of her findings to the U.S. Attorney for the Southern District of New York and the IRS, which could bring criminal charges.

New York City

The Manhattan DA’s office has been looking into the same alleged scams.  When a new D.A. stopped presenting evidence about Trump’s possible criminal conduct to a grand jury, two senior prosecutors quit in protest.  Reportedly, some people in the D.A.’s office feared they’d have trouble getting a conviction because it would be hard to prove intent. The Manhattan DA has gotten a guilty plea from Weissellberg, who has agreed to pay roughly $2 million in back taxes and to testify against the company — but not against Trump personally.

And yet, if Trump is prosecuted for his part in the tax-avoidance scheme, what will his story be? What do the facts really prove?  The chief financial officer pleads guilty to violating tax laws by accepting non-cash perks instead of on-the-books cash compensation.  Could this have happened without at least the acquiescence of other top executives?  Did they include Trump himself?  If Trump claims, as he surely will, that he knew nothing about the highly-irregular compensation of his chief financial guy is he saying that his whole brilliant-businessman routine is just a farce, that really he’s just an innocent doofus who doesn’t even know what’s going on in his own company?  If anyone does try to prosecute him personally, it will be interesting to see how he explains it all.

Both the alleged efforts to subvert the electoral process and the alleged financial sleaze would be very much in character; they’re part of what has become Trump’s de facto brand.  But hauling all those papers down to Florida just looks . . . kind of odd.  

Mar-a-Lago Papers

Those Mar-a-Lago papers seem to be – but may not turn out to be – another legal slam-dunk.  He had the papers.  He shouldn’t have had the papers.  His lawyers said he had given the papers back. He hadn’t. The papers contained sensitive information.  How can he not be guilty?  

It’s hard to know what the former President’s intent really was.  “Here’s my hunch,” conservative columnist Bret Stephens suggested recently in The New York Times: “Donald Trump has only a vague idea of what’s in all of these documents. The notion that he read through boxes and boxes containing hundreds of documents with classification markings and chose to take these particular items strikes me as … unlikely.”  Maybe it was a bit like scooping up all the unused mini-bottles of shampoo before you leave the hotel room.  Which doesn’t mean it was legal.

It is, in fact, illegal to remove either Presidential or agency documents.  And what about those documents that were classified?  Trump claims he declassified them. That isn’t plausible. He may have thought it – he recently said he could in fact declassify documents by “thinking about it” — although he probably didn’t, but the thoughts of the Great Leader aren’t enough; there presumably has to be some documentation.  No one has offered any.  And a number of former high-ranking White House officials have publicly said the claim is nonsense. 

The Special Master

U.S. District Judge Aileen Cannon, a Trump appointee, has granted Trump’s request to have the Mar-a-Lago papers reviewed by a special master.  (A cynic might say Cannon already seemed to have a special master: the guy who appointed her.)  The special master’s review is meant to identify documents that may be subject to executive or attorney-client privilege. While this review goes on, the FBI must pause its investigation.  A national security review can continue.  This process may delay the FBI investigation of the papers for months.  

At his very first hearing on the Mar-a-Lago documents, the special master, Raymond J. Dearie – chosen by Trump – made it clear that he’d seen no evidence and that in the absence of any such evidence, he’d take the government’s word that the documents were indeed classified. Federal law says it’s a crime when anyone “knowingly and willfully communicates, furnishes, transmits, or otherwise makes available to an unauthorized person, or publishes, or uses in any manner prejudicial to the safety or interest of the United States.”

Cannon rationalized her decision to appoint a special master by saying, in part, that “[a]s a function of plaintiff’s former position as president of the United States, the stigma associated with the subject seizure is in a league of its own,” Cannon wrote in her order. “A future indictment, based to any degree on property that ought to be returned, would result in reputational harm of a decidedly different order of magnitude.”

In the real world, this is simply nonsense.  Reputational harm?  Really? To Trump?  What about the  Access Hollywood” tape on which he said that as a celebrity, one could do anything to women, even “grab them by the pussy?”  Telling Georgia’s secretary of state Brad Raffensperger that he requested to “I just want to find 11,780 votes?”  The $130,000 payoff to former porn star “Stormy Daniels?”  The many allegations of sexual misconduct, including harassment and assault?  The $25 million payment to settle a fraud suit against Trump University.  

Executive privilege?  

Wait: he’s no longer the executive.  The guy named Biden who is the executive hasn’t asked for it.  Last year, Trump failed to keep the National Archives from giving records to the House committee investigating the January 6 attack on the Capitol. 

And yet . . . can a non-executive claim executive privilege?  Well, yes, in certain circumstances, SCOTUS said in 1977, largely invalidating a deal that ex-President Richard Nixon had cut with the General Services Administration.  A former President might be able to keep some communications about policy development secret . . . BUT the range of communication would have to be narrow. (Nixon could “legitimately assert the Presidential privilege, of course, only as to those materials whose contents fall within the scope of the privilege recognized in United States v. Nixon. In that case the Court held that the privilege is limited to communications ‘in performance of [a President’s] responsibilities . . .of his office,’ and made ‘in the process of shaping policies and making decisions,’” 

And the current President might be a better judge of what should be protected than a former one.  “[I]t must be presumed that the incumbent President is vitally concerned with and in the best position to assess the present and future needs of the Executive Branch.” Also, the strength of the privilege would erode with time. (“The expectation of the confidentiality of executive communications . . . has always been limited and subject to erosion over time after an administration leaves office.”)

And the purpose of executive privilege was to further the interests of the nation, not the interests of the person who claimed it.  (“[T]he privilege is not for the benefit of the President as an individual, but for the benefit of the Republic…”]  The Court used that as a justification for extending executive privilege beyond an individual’s term.  But the same logic could be used to rule against a privilege claim that clearly furthered only an ex-President’s personal interest. 

When the federal government moved to gain access to the roughly 100 classified documents in the Mar-a-Lago trove, a three-judge panel of the 11th Circuit (two of the judges were appointed by Trump) declared, “we cannot discern why [Trump] would have an individual interest in or need for any of the 100 documents.”  The judges explained that “a person may have access to classified information only if . . . he ‘has a need to know the information.’”  In this case, “[Trump] has not even attempted to show he has a need to know the information.”

Running out the Clock

Justice delayed is justice denied,” so they say.  Donald Trump doesn’t seem to want justice.  He does want delay.  And why not?  It’s a time-honored legal tactic.  And there are special circumstances here.  If Republicans win back Congress, there will be no more committees investigating what he did on and before January 6.  Merrick Garland will still be Attorney General, but Congress could certainly put pressure on him and the Justice Department.  If Trump becomes a candidate for President, the Justice Department may back off, and if others don’t, appeals to the federal courts would have a better chance of success.  And if he is re-elected, well, he won’t have anything to worry about before 2029.  Oh yes; and he can pardon his convicted cronies plus anyone else who might be tempted to testify against him.  


There are plenty of unknowns.  We don’t know what those people  have said or will say to grand juries. We don’t know whether or not the Justice Department will prosecute him.

Merrick Garland has said that “no person” is above the law” and therefore “[we have to hold accountable every person who is criminally responsible for trying to overturn a legitimate election.” Judge Cannon evidently disagrees.  She made it clear she thought an ex-President deserved legal deference that the rest of us do not.  Fortunately, she’s not the attorney general.  Yet.

Other known unknowns: We don’t know what the charges will be. We don’t know how juries or judges will decide. We don’t know how long Trump’s delaying tactics will postpone their decisions. If procedural questions or convictions are appealed to the Supreme Court, we don’t know how a majority of justices will rule.  

The Supremes

Will the Supreme Court support Trump?  Maybe not.  The new conservative members are ideologues – or, if you prefer, smug theocrats – but they aren’t necessarily MAGA cultists.  They have lifetime appointments, so they don’t have to please Trump any more. There’s no reason to doubt that they really do believe in the rule of law. 

Whatever Trump’s Supreme Court appointees decide, what about his supporters?  Trump’s legal troubles notwithstanding, most Republicans still think he should be the party’s candidate in 2024.  Will anything change their minds?  I wouldn’t bet on it.

Summing Up

As Trump himself has said, he can run for office again even if he’s indicted.  Will he be?  He was a shockingly unqualified President and seems to be a shockingly vile human being.  Neither of those things is a crime.

Has he committed crimes?  Probably.  Will he be indicted for them?  Possibly.  Will we see him in prison?  Don’t hold your breath.


  1. Stopped reading when you posited Nixon committed treason and take issue that you don’t mention the current VP’s riot inciting offering to pay bail for miscreants + Biden’s brilliant assessment of Georgia’s voting law as “Jim Crow 2.0” without reading it.
    It would be nice to read a democratic review of why ‘no term abortion’ is a good thing for America, and how a $400,000,000.00 gift to 10% of the population is legal.
    Let the Trump issues play out, look in that political mirror and explain your positions not just keep reminding of the prior administration’s many flaws

  2. Aaaah, good ole’ Post Alley. As WW3 looms, as Europe looks poised for a new Dark Age, Post Alley keeps alive the flame of Trump Derangement Syndrome. Sure, Orange Man is a buffoon, has bad table manners, etc., etc., etc……

    Yet here we are, with the lower decks flooding as the rudderless, leaderless ship of state founders. How to respond? Hoist high the banner of TDS. Ignore all else.

    Will the gerontocracy of Seattle’s chattering class ever wake up to the real world? One looks in vain for any sign.

  3. Oh yes, the sky continues to fall.

    As a small child, some 65+years ago, I do recall the occasional practice of ducking under our desks at Assumption School just off NE 65th St in Seattle just in case we were beset upon by a nuclear warhead. Of course at that age, I recall school’s nuns were far more fearsome on a regular basis than the possibility of a nuclear bomb hitting our school. Oh, I also recall our neighbor digging a bomb shelter in his backyard that the kids in the neighborhood eventually regularly played in after its completion.

    Oh, and Europe was in a Dark Age back then too.

  4. What I find refreshing about this legal analysis is its skepticism about actually convicting Trump, a master of evasive tactics that score political points but don’t create legal problems. The usual coverage of these issues is to find reasons for indictments and public disgrace. That’s well short of winning in a court room.


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