Trump Faces Five Major Investigations. He Has Dozens of Ways Out.
Nov. 17, 2022
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By Ankush Khardori
Illustrations by Antonio Giovanni Pinna
Mr. Khardori is a lawyer and legal analyst. He spent several years as a prosecutor at the Department of Justice. Before he joined the federal government, he defended corporate clients against charges of fraud and other crimes.
Donald Trump and his business empire are currently the subjects of no fewer than five major simultaneous investigations, a truly extraordinary challenge for anyone, let alone a former and possibly future president of the United States. These are complicated investigations, with long and winding paths to resolution. They involve scores of federal and state investigators and witnesses across the country, from politicians eager to shield themselves from scrutiny to employees turning on their colleagues to a former president who knows how to navigate — and manipulate — the legal system like no one else.
Trump is facing five major investigations
The Classified Documents InvestigationDid Trump illegally remove classified documents from the White House and obstruct investigators?
The Jan. 6 InvestigationDid Trump try to incite an insurrection, commit election fraud or fraudulently fund-raise in the run-up to Jan. 6?
The Manhattan District Attorney’s InvestigationDid the Trump Organization commit tax fraud or other financial crimes?
The Georgia Election InvestigationDid Trump break the law to try to overturn his 2020 election loss in Georgia?
The New York State Civil CaseDid Trump and his children lie to lenders and insurers about the Trump Organization’s financial condition?
The public has very little visibility into how these investigations are proceeding day by day, as government officials quietly gather evidence and plan their next moves. Any number of unexpected developments — surprise witnesses, hung juries and perhaps even a special counsel empowered to oversee Justice Department investigations — could slow or derail their work. The announcement of Mr. Trump’s candidacy for president does not halt any of these investigations, but it could affect how prosecutors weigh their options, and his uniquely polarizing status could affect how judges and juries resolve any cases that make it to trial. Were he to win the election, he could put an end to any pending federal prosecutions or investigations once in office. Even at this stage, some potential scenarios are possible to discern, including the possibility — however improbable it may seem — that all of the investigations resolve in his favor, with no conviction and no serious legal consequences. Based on interviews with experts and analysis of media reports, as well as of the law itself, here is a close look at some of the paths by which such an outcome could come to pass.
Below we illustrate the likely key steps for prosecutors and other enforcement officials, as well as offramps Mr. Trump could use to stay out of prison or otherwise mitigate the possible repercussions from these probes.
The Classified Documents Investigation
Did Trump illegally remove classified documents from the White House and obstruct investigators?
PRETRIAL
The Justice Department concludes its investigation
Mr. Trump briefly managed to limit the department’s investigation in September by requesting the appointment of a special master to review the documents and decide which investigators could use. But in a twist, the 11th Circuit Court of Appeals, including two judges that Mr. Trump appointed, allowed government investigators to continue their work with the most crucial documents, and the Supreme Court refused to get involved. Now that Mr. Trump has announced his presidential candidacy, Attorney General Merrick Garland, to avoid the appearance of a conflict of interest, might opt to switch tactics and hand the investigation over to a special counsel. To imagine how that might work out, picture Robert Mueller, whom Mr. Trump was able to turn into a handy villain to rail against.
OfframpJustice Department decides not to bring charges
Prosecutors could conclude that the evidence isn’t strong enough to win a conviction or that prosecution wouldn’t serve a “substantial federal interest” under department guidelines. Mr. Trump’s lawyers will almost certainly try to make this case.
Justice Department decides to bring charges
This would make U.S. history: the first criminal case against a former president. Charges could include some or all of the three crimes listed in the search warrant for Mar-a-Lago — unlawfully retaining national defense information, stealing or destroying government documents and obstructing a federal investigation — and depending on the results of the investigation, there could also be others, like lying to the government.
OfframpTrump barrels ahead with his presidential campaign—now under indictment
There are no rules against this. If anything, being under indictment might help Mr. Trump galvanize his base.
Trump is elected president
Even today, it is far from clear who would win a Biden-Trump rematch, but if elected, Mr. Trump could appoint an attorney general who would close any lingering Justice Department investigations.
Trump pardons himself
No one has ever tried, so there’s no clear answer to whether a president can pardon himself. But as a practical matter, who could stop him? It’s not as though his own administration’s Justice Department would prosecute him.
 TRIAL
OfframpTrump gets case dismissed
Defendants often try to get charges dismissed at the outset. It’s not easy; Mr. Trump would most likely need to show that the government’s theory of the case has a fatal legal defect. He has shuffled through a number of claims of varying credibility — including that he could secretly declassify documents with his mind — but a cogent defense theory has yet to take shape.
OfframpJury hangs
If most members of the jury vote to convict but even one refuses, the result would be a hung jury, a mistrial and a gigantic political mess.
OfframpJury acquits
If you’re a defendant in a federal criminal trial, your odds are generally terrible. Federal prosecutors win about 85 percent of cases that go to trial. They tend to fare worse in particularly hard cases, though, and this would be a knock-down, drag-out legal fight, with a complex set of facts, a lack of clear precedent and the backdrop of a notoriously chaotic White House. There’s no telling where it would end up.
Justice Department admits defeat and decides not to try Trump again
Sometimes prosecutors take another shot; sometimes they don’t. A second trial with a new jury would be highly controversial, fueling accusations of a political witch hunt. The department might conclude that it just wouldn’t be worth it.
Jury convicts Trump
The vast majority of federal defendants who go to trial are convicted. Politically, this would be an earthquake, but legally, it would be par for the course.
 POSTTRIAL
OfframpTrump argues against prison sentence
After a defendant is convicted in federal court, the judge often considers proposals from the defense and the government. Possible outcomes would be prison time, supervised release, home confinement, a fine or some combination thereof. If convicted, Mr. Trump would almost certainly argue against prison time, and the judge might well agree.
OfframpTrump drags out sentencing process until after election
Sentencing usually takes place a few months after a trial, but if Mr. Trump is the G.O.P.’s 2024 nominee, he could argue that the judge should delay until after Election Day. Even the most by-the-book judge would need to take such a request seriously.
Trump is elected president
Mr. Trump could appeal to voters to prevent his imprisonment and allow him to seek retribution. Even if that strategy fails, Mr. Trump might hope that the pressure — political or otherwise — from his supporters would influence the sentencing judge in his favor.
Trump pardons himself
If all else fails, this can be done even if the criminal case is pending. Just ask Steve Bannon.
Trump faces prison
Unless Mr. Trump is in the Oval Office, the unthinkable could happen: A former president of the United States could be sentenced to time behind bars. Some other democracies have survived a destabilizing development like that, but Mr. Trump and his most dedicated supporters are a notoriously unpredictable lot, and the risk of serious violence would be real.
OfframpTrump tries to get verdict thrown out
Remember Adnan Syed? A trial isn’t necessarily the end of a criminal case. Defendants have the opportunity to file posttrial motions and appeals that can take years to resolve, and Mr. Trump could stay out of prison while all of this unfolds.
Trump asks judge to overturn verdict
Mr. Trump could argue that the evidence was legally insufficient for the jury to convict him. Motions like these ordinarily face long odds, but a sympathetic judge could surprise the country. Again.
Trump turns to court of appeals
If Mr. Trump can’t persuade the trial judge to do it, he might ask a supportive appeals panel to toss out his conviction. Even in more routine cases, this is rare, but it happens, and Mr. Trump might face some of his appointees.
The Supreme Court makes final decision, affirming or overturning conviction
Mr. Trump appointed three of the current justices. To date, they have been less indulgent of him than you might expect, but a situation like this would be completely without precedent, so there is no sure way to predict how it would go.
Trump goes to prison
If he is convicted and sentenced to incarceration and if the verdict and sentence are upheld on appeal and if he is not yet in a position to pardon himself, he could do time. But that’s a lot of ifs.
OfframpTrump runs for president from prison
If the unlikely outcome of a prison sentence should come while Mr. Trump is still running, he could in theory continue to campaign from his cell. Conviction on certain criminal offenses could preclude him from serving in federal office, but Mr. Trump would likely frame any attempts to remove him from the ballot as violating voters’ constitutional rights, and he could well be correct.
Trump is elected president and, still in prison, promptly pardons himself
One for the record books.
The January 6th Investigation
Did Trump try to incite an insurrection, commit election fraud or fraudulently fund-raise in the run-up to Jan. 6?
 PRETRIAL
Prosecutors look closely at the days and weeks before the riot
In response to Mr. Trump’s presidential candidacy, Mr. Garland might hand this investigation to a special counsel to avoid the appearance of a conflict of interest. Either way, the questions that prosecutors will try to answer include: What did Mr. Trump tell his closest aides about the prospect of violence on Jan. 6? What did he know about the involvement of the Proud Boys or the Oath Keepers in the protests planned for that day? Did he really believe his wild election fraud theories? At the moment, Mr. Trump’s legal team is trying to prevent the Department of Justice from obtaining information that might answer those questions, claiming it’s covered by executive privilege. So far, he’s losing.
OfframpTrump successfully invokes executive privilege
Without crucial details from key witnesses, the Department of Justice might never get to the bottom of what Mr. Trump did leading up to the Capitol riot because he was president at the time.
OfframpJustice Department decides not to bring charges
As in any other criminal investigation, prosecutors could conclude that the evidence isn’t strong enough to secure a conviction at trial or that prosecution wouldn’t be a good use of federal resources. You don’t have to look far to find examples of this.
Justice Department decides to bring charges
The department could seek to criminally charge Mr. Trump with obstruction of an official government proceeding (the congressional certification of Joe Biden’s election) or conspiracy to defraud the government, as well as charges directed at election fraud, incitement of insurrection or seditious conspiracy.
Justice Department charges Trump based on violence at Capitol
Over the summer, you might have read that the Jan. 6 committee found a smoking gun demonstrating Mr. Trump’s plan to incite a violent siege of the U.S. Capitol. This wasn’t true. It is far from clear whether he could be held criminally liable for the violence at the Capitol; this would likely depend on whether he was aware of the plans and preparations for violence.
Justice Department charges Trump over fake electors scheme
To prosecute Mr. Trump for supporting the fake (or “alternate”) electors put forward by some Republicans, the department would need to conclude not just that he was aware of the effort but also that his conduct was a crime — perhaps obstruction of an official government proceedin g or conspiracy to defraud the government.
Justice charges Trump with fraudulent fund-raising tactics
Mr. Trump is no stranger to financial fraud investigations, but federal criminal fraud cases are notoriously difficult for prosecutors to build. The Department of Justice is investigating whether Mr. Trump’s Save America PAC misled donors about how their money would be used after the election. To charge him, however, the department would need to prove that Mr. Trump was personally involved in or aware of these tactics.
Justice charges Trump with ... something else
In recent months, the Justice Department has expanded its investigation and sought testimony from senior Trump White House officials, possibly scrutinizing conduct that the Jan. 6 committee has focused on relating to Mr. Trump’s false claims of election fraud and his effort to persuade Vice President Mike Pence to reject the certified electors.
OfframpTrump keeps running for president — even after the indictment
Mr. Trump’s presidential run may be his most potent defense strategy, perhaps discouraging some witnesses from cooperating for fear of running afoul of the next president of the United States, who during his last term demonstrated a willingness to use the Justice Department against his political enemies.
Trump is elected president
Whoever he nominates for attorney general could presumably stop prosecuting the case — and he or she could ask the court to dismiss the charges on the theory that the executive branch has essentially total discretion to determine whether to pursue criminal charges against anyone, including the president.
Trump pardons himself
If Mr. Trump is elected, he could undertake the nation’s first presidential self-pardon even before a trial commences, which would likely end any active federal investigations or prosecutions that implicate him.
 TRIAL
OfframpTrump moves to dismiss case
If the case goes to court, Mr. Trump’s own legal history suggests he would submit an aggressive broadside painting himself as the victim of political persecution.
OfframpJury acquits
A large portion of the country — and potential juror pool — has extremely negative feelings about Mr. Trump, and about half the country already thinks he should be criminally charged. Still, a jury could decide that the evidence is not compelling enough to justify the first criminal conviction of a former president in American history.
OfframpJury hangs
Mr. Trump would be an unusual defendant in many ways, and one of them would be the difficulty of finding jurors who regard one of the country’s most recognizable and polarizing people entirely without bias. In a case of this magnitude, with this much uncharted territory, it’s easy to imagine irresolvable disagreements in the jury room or the presence of a die-hard loyalist who might refuse to convict, regardless of the evidence.
Justice Department admits defeat and decides not to try Trump again
The department could attempt a redo — and try to convict Mr. Trump in a second trial with a new jury — but that would be extremely controversial. Sympathetic observers among the public and in conservative media could decry the effort as political persecution, and with Mr. Trump campaigning for president, the Justice Department would need to think long and hard about putting the country through the public turmoil and divisiveness of another trial.
Jury convicts Trump
A conviction would, at a minimum, cause a political firestorm. With right-wing political violence metastasizing, the federal government would no doubt beef up security arrangements during a trial and certainly after a conviction — for prosecutors, the judge, court staff members and the jury.
POSTTRIAL
OfframpTrump argues against a prison sentence
You would not want to be the judge sentencing Mr. Trump. The public and the media would have a great deal to say — as, of course, would Mr. Trump, who would have every reason in the world to fight for his liberty. But he might not have to fight very hard; even if a jury convicted him, it’s far from clear that the judge would want to send a former president to the clink.
OfframpTrump drags out sentencing process until after election
If Mr. Trump is still running for re-election while the sentencing process is in motion, he would want to make it drag on as long as possible so that he has time to win re-election and then pardon himself.
Trump runs for president while awaiting sentencing
He could be the first felon with a plausible path to the White House. If the Department of Justice successfully prosecuted Mr. Trump for incitement of insurrection, however, there would be a serious question about whether Mr. Trump is prohibited from serving as president under the 14th Amendment, which precludes those who have “engaged in insurrection or rebellion” from holding federal office. Congress might even try to step in to disqualify him from running again.
Trump is elected president
No one who witnessed the 2016 election — remember the “Access Hollywood” tape? — should count him out, even after a conviction.
Trump pardons himself
The Holy Grail. The sixth Infinity Stone. The endgame for Mr. Trump would be to secure a position of overwhelming legal power to keep him out of prison.
OfframpTrump tries to get verdict thrown out
Juries are vitally important to our criminal justice system, but they do not have the last word in a criminal case. If Mr. Trump is convicted, expect a sprawling posttrial effort that would make the convoluted litigation over the Mar-a-Lago search look comparatively straightforward. The first step for Mr. Trump could be to ask the judge to overturn the verdict. That outcome would be extremely unusual but is one that a sympathetic judge could make happen.
Trump turns to a court of appeals
The likeliest venue for a trial about efforts to overturn the election would be the District of Columbia. If Mr. Trump was convicted and sought an appeal, the relevant court has three Trump appointees.
Supreme Court makes final decision, affirming or overturning conviction
The justices have not favored Mr. Trump’s legal claims so far, but the Supreme Court’s conservative majority is not afraid of issuing unprecedented rulings that generate extraordinary political controversy.
Trump goes to prison
No, this is not the likeliest scenario, but still: If the Supreme Court affirms a sentence of incarceration, Mr. Trump could in theory end up in a federal prison. Which one? A low-security federal facility could be a contender. The federal government might even invent some housing arrangement.
OfframpTrump runs for president from prison
Mr. Trump ending up behind bars? Improbable, but you never know. Mr. Trump, under those circumstances, refusing to bow out? You can count on it. What might this campaign look like? A vice-presidential candidate and surrogate operation on the campaign trail, coupled with periodic missives from the candidate-turned-inmate. Don’t count on a presidential debate.
Trump is elected president
If this sounds inconceivable to you, it’s time to catch up on news out of Israel, where Benjamin Netanyahu is poised to return to power despite a long-running criminal case against him.
Trump pardons himself
Mr. Trump is fond of self-dealing. Writing his own get-out-of-jail-free card would be the next frontier.
The Manhattan District Attorney’s Investigation
Did the Trump Organization commit tax fraud or other financial crimes?
PRETRIAL
OfframpTrump avoids prosecution
This year, based on the evidence that investigators had collected, the newly elected Manhattan D.A. declined to file charges against Mr. Trump. Allen Weisselberg, the Trump Organization’s chief financial officer, is on the stand this week testifying against the company, but he struck a plea deal that ensured he would not implicate his boss. In theory, Mr. Trump’s candidacy has no legal effect on this investigation, and presidential pardons don’t apply to state charges. The D.A. has repeatedly said the investigation remains open. But based on the publicly available information, it’s looking unlikely that it will result in any charges against Mr. Trump.
Investigation heats up
There is still a chance, however, that the D.A. finds some compelling new evidence and brings charges against Mr. Trump after all. If so, it would be the former president on trial, not just his company.
 TRIAL
OfframpJury acquits Trump Organization
So far, the Trump Organization has argued that Weisselberg is lying to help himself and that the company didn’t benefit from his misdeeds. If the jury buys either of these arguments, it could acquit the company.
OfframpJury hangs
Mr. Trump once said he could shoot someone on Fifth Avenue and he wouldn’t lose any voters. Even a seemingly open-and-shut case could be thrown into disarray by a single intransigent juror.
Jury convicts
Don’t be surprised if a trial ends up in a conviction of the Trump Organization. Although this would be a major public win — especially for a D.A. who has been described as soft on crime — it’s unlikely that the company would suffer any serious harm. Corporations can’t be imprisoned, so the main punishment would likely be a fine, perhaps coupled with some sort of period of corporate probation. The New York Times has estimated that the fine could come out to $1.62 million — hardly the kind of money that would bankrupt the company.
 POSTTRIAL
OfframpTrump Organization appeals
It would be an uphill battle, but the company could try to appeal the conviction or the sentence.
OfframpTrump Organization suffers no major fallout
While some of the Trump Organization’s lenders might be able to call in their loans if the company is convicted, they could well choose not to upset the apple cart and instead just keep collecting loan payments.
The Georgia Election Investigation
Did Trump break the law to try to overturn his 2020 election loss in Georgia?
 PRETRIAL
OfframpTrump allies avoid testifying
The Atlanta-area district attorney’s office has issued a raft of grand jury subpoenas this year, including subpoenas to Trump allies like Mark Meadows, a former White House chief of staff, and Senator Lindsey Graham. Prosecutors are trying to find out more about efforts to pressure Georgia’s secretary of state, Brad Raffensperger, to overturn the state’s election results and to create a slate of fake electors. So far, the Trump allies’ efforts to resist testifying have failed, but if key witnesses prevail, that could slow the prosecutors’ work or, in the worst-case scenario, kill the investigation altogether.
OfframpD.A.’s office backs down and decides not to charge Trump
Like the Justice Department, District Attorney Fani T. Willis could decline to file charges against Mr. Trump, either because she concludes that she doesn’t have sufficient evidence to convict him or as a matter of prosecutorial discretion.
D.A.’s office brings charges
A local prosecutor criminally charging a former president based on conduct while he was in office would be strange in our constitutional system, but there’s nothing stopping Ms. Willis from indicting Mr. Trump if she and her team decide that they have sufficient evidence of crimes. The D.A.’s office might conclude, for instance, that charges against Mr. Trump are warranted as a result of his infamous call to Mr. Raffensperger (remember “I just want to find 11,780 votes”?) or his involvement in the use of fake electors in the state.
OfframpTrump forges ahead with his presidential campaign — now under indictment
Presidents can’t issue pardons for crimes against state law, so even if he is elected, Mr. Trump wouldn’t be able to pardon his way out of this one. As a presidential candidate, however, he could complicate matters by claiming that the prosecution is politically motivated and that any trial should be put on hold until the campaign is over.
TRIAL
OfframpTrump moves to dismiss case
If Mr. Trump is charged, his lawyers will no doubt look for some mechanism to get the case thrown out before trial, but it’s rare for a state court judge to dismiss criminal charges at the start of a case.
OfframpTrump moves case to federal court
One considerable wrinkle here is that Mr. Trump may argue that the case implicates his constitutional duties and prerogatives. That could be enough to get the case transferred to federal court and perhaps reviewed by the 11th Circuit Court of Appeals — and even the Supreme Court — before a trial occurs.
OfframpJury acquits Trump
Never say never.
OfframpJury hangs
More than a quarter of Fulton County’s residents voted for Mr. Trump. Even if most jurors vote to convict, a single loyalist could hang the jury and force a mistrial. A federal jury pool, which would be drawn from the larger Northern District of Georgia, would likely be even more favorable for Mr. Trump.
D.A.’s office admits defeat and decides not to try Trump again
Prosecutors sometimes retry cases after a mistrial if they think they should have won the first time, but in this case, the public pressure to drop the case could be overwhelming.
Jury convicts Trump
Criminal trials usually result in convictions, though this rule of thumb is less reliable in state courts than in federal courts.
 POSTTRIAL
OfframpTrump avoids prison
A state court sentencing a former U.S. president to prison time would be a surreal artifact of our constitutional system — and an explosive political development that a judge might be highly motivated to avoid. Mr. Trump would be similarly motivated; if he found himself at this juncture, he would presumably argue for a suspended sentence, which would effectively put him on probation.
OfframpTrump delays sentencing and keeps campaigning
He would likely work to push any sentencing off until after the 2024 election. As it was in the recent midterm elections, Georgia will likely be a 2024 battleground state. Convicting Mr. Trump there could further scramble its already unpredictable political status.
Trump is elected president
While the president’s pardon power doesn’t cover state crimes, it is almost impossible to imagine that a state court would (or could) imprison a duly elected U.S. president while in office.
OfframpTrump tries to get verdict thrown out
Mr. Trump could ask the presiding court to vacate or overturn the conviction on the grounds that the evidence was insufficient or that there was some defect in the proceedings.
Trump turns to appeals court
If the trial judge doesn’t help Mr. Trump out, maybe an appeals court would.
Supreme Court rules
This case would almost certainly go to the Supreme Court, which would have to weigh in on the unprecedented questions about presidential power and the role states can play in checking it.
Trump goes to prison
Lock him up? This is an extremely unlikely outcome, but then again, this is an extremely unlikely situation to begin with. If the election is ongoing, Mr. Trump could continue to campaign from prison. It happened in 1920, when the well-known socialist and antiwar activist Eugene Debs ran for president from prison in Atlanta.
OfframpTrump is elected president
Mr. Trump would not be able to pardon himself, but winning re-election would substantially complicate — and perhaps halt — the proceedings while he is in office and presumably result in his release.
The New York State Civil Case
Did Trump and his children lie to lenders and insurers about the Trump Organization’s financial condition?
 PRETRIAL
OfframpTrump settles with A.G.’s office
Although it was brought by the government, this is a civil case, not a criminal prosecution — which means there is a lower burden of proof and no risk of prison time. Mr. Trump’s presidential candidacy or even election would not prevent the case from moving forward, though it might make the A.G.’s office more likely to settle. Less than two weeks after Mr. Trump was elected in 2016, he settled a case about Trump University with the A.G.’s office. This time, too, he could decide — to get ahead of the charges, to minimize the legal costs or to just move on — to put the case behind him.
TRIAL
OfframpTrump gets the case dismissed
His odds of success are very low, particularly because the A.G. has sued using a notoriously broad state law, but it could happen.
OfframpTrump mounts successful defense
Mr. Trump doesn’t need to beat all of the A.G.’s claims at trial to emerge relatively unscathed. One plausible trial strategy would be to demonstrate that the alleged conduct, even if it occurred, caused little (if any) actual harm to his company’s lenders and insurers.
 POSTTRIAL
Attorney general wins at trial
Because this isn’t a criminal case, the A.G. doesn’t need to establish beyond a reasonable doubt that Mr. Trump broke the law — merely that it’s more likely than not that he did.
OfframpTrump argues for low monetary penalty
While the A.G.’s lawsuit seeks $250 million, along with a variety of restrictions on Mr. Trump’s ability to do business in the state, the court could fashion a different set of remedies — including a much lower monetary penalty — after hearing the evidence at trial.
Trump appeals verdict
Mr. Trump could still appeal, but his prospects would be substantially constrained by the attorney general’s relatively low burden of proof, the expansive and potent law underlying the complaint and the broad deference accorded to the office by New York courts. Most likely, the initial verdict would stand. |
