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Are the walls really closing in on Trump this time?

His legal problems are worsening. But they might not take him down.

 Trump in front of a microphone.
Former President Donald Trump spoke at the Covelli Centre in Youngstown, Ohio on September 17, 2022.
Andrew Spear for The Washington Post via Getty
Andrew Prokop is a senior politics correspondent at Vox, covering the White House, elections, and political scandals and investigations. He’s worked at Vox since the site’s launch in 2014, and before that, he worked as a research assistant at the New Yorker’s Washington, DC, bureau.

Stop me if you’ve heard this one before: New developments have put Donald Trump in even more serious legal jeopardy.

A new civil fraud lawsuit from the New York attorney general’s office is threatening his business, while his efforts to stall the criminal investigation into whether he mishandled classified information seem to have failed. And a separate investigation into the January 6 attack scrutinizes his associates.

It all looks quite bad for him. Then again, for at least five years, much of the media has touted the seriousness of Trump’s legal peril, portraying him as on the verge of a humiliating downfall — only to see him go, in his own words, “Scott Free,” again and again.

The Mueller investigation, the Michael Cohen investigation, the first impeachment, the second impeachment, and the Manhattan district attorney’s probe were each hyped as the thing that could bring Trump down. Yet they all either fizzled out or went quiet, with Trump remaining conspicuously, well, un-brought-down.

So will this time be different? Are the walls really closing in?

It certainly seems like Trump’s threat of facing criminal charges is currently higher than it’s been since he entered politics, due to the classified documents probe, and the fact that he’s no longer an incumbent president with immunity against indictment. The New York civil lawsuit — at least on its face — appears to present a serious threat to his business as well. The suit claims Trump and his employees “violated a host of state criminal laws” and their conduct “plausibly violates federal criminal law,” and New York Attorney General Letitia James said she’d refer her findings to federal prosecutors.

But it’s worth remembering Trump hasn’t been criminally charged with anything yet, and that prosecutorial caution could still prevail. Even if Trump is charged, a potential trial would present further challenges, and if he is convicted, an eventual sentence might not be so harsh. And though he is facing that New York civil suit, a trial there is no sure thing either.

Trump critics hoping he will be removed from politics via indictment or prison may be hoping in vain. If he chooses to run again, it’s likely to be voters who will decide his fate.

What prosecutors will consider before pursuing a Trump indictment or trial

Whatever you believe about the strength of the evidence against Trump in these various investigations, his status as incumbent president meant he couldn’t be indicted during his term, according to long-standing Justice Department policy. And his continued popularity among Republican voters meant that impeachment would end in acquittal (because many Senate Republicans would have been required to convict him). So, from January 2017 to January 2021, the power of his office and the power of his political base protected him.

Since Trump left office, his shield against indictment is gone. And while his political base on the right remains strong, the arena has changed — Republican politicians are no longer the key decision-makers.

Instead, prosecutors have the reins. Various prosecutors — in New York, in Washington, DC, and in Georgia — have scrutinized Trump’s conduct for potential crimes in recent years, looking into his company’s business practices, his attempt to overturn the 2020 election result, and whether he improperly brought classified documents to Mar-a-Lago.

These prosecutors will have to evaluate the strength of the evidence against Trump, assessing whether he indeed did commit crimes and whether they’d likely convince a jury of that at trial. Federal prosecutors will also have to persuade higher-ups like Attorney General Merrick Garland.

Gaming out these prosecutors’ thinking is difficult because we don’t have access to the evidence they’re looking at, or their legal reasoning. For each of the Trump investigations, we don’t know whether they think they’re looking at a clear open-and-shut case of criminality, whether their legal theory is backed by ample precedent or is a bit novel, or whether similar cases tend to be brought in similar situations. (Trump’s attempt to overturn the election has little if any modern precedent in the US, so it’s difficult to even know what to compare it to.)

But for many prosecutors, particularly in the US Justice Department, caution reigns supreme. Pursuing an indictment and trial in a high-profile matter takes a great deal of resources, and presents the risk of embarrassment should the trial end in acquittal. DOJ’s prosecution manual says that government attorneys should not only consider whether they believe the person committed a crime, but also whether “the admissible evidence will probably be sufficient to obtain and sustain a conviction.”

So prosecutors typically look for a clear-cut, open-and-shut crime. The classified documents matter might seem like one such crime: Trump had the documents, he should not have taken them, so they might reason he arguably should be charged.

Still, there are many complications that could make the government wary of a potential trial. For one, they want to keep the documents secret. Depending on whether the venue is in Florida (it’s currently unclear where they’d charge it), a jury conviction could be difficult. And while Trump’s arguments about executive privilege might seem like a stretch, this Supreme Court hasn’t weighed in on them just yet.

Note that when former CIA director David Petraeus was investigated for leaking classified material to his biographer, he eventually struck a plea deal for two years of probation and a $100,000 fine. Trump’s conduct is still murky so perhaps it was worse, and he’s unlikely to strike a plea deal like Petraeus did, but Petraeus actually did leak the information and Trump is not known to have done so. If a case were to be brought, and Trump was to be found guilty, he could face similar consequences — or even a less severe punishment.

Now, prosecutors in Georgia and New York are elected Democrats and might be more willing to take risks to go after Trump. But even they might have reasons for caution. A Trump indictment and trial would swallow up everything else their office might do for years to come and become a grueling effort, while they’d personally become a top target of Fox News and the right. Even if that doesn’t give them pause, they could simply decide they don’t have a strong enough case.

Earlier this year, Alvin Bragg, a criminal justice reformer elected as Manhattan’s District Attorney, reportedly expressed doubts about the ongoing investigation into Trump’s business practices he had just taken over, and two prosecutors leading it soon resigned. (Bragg insisted in a statement this week that his office’s Trump investigation was “active and ongoing.”)

On Wednesday, New York Attorney General Letitia James filed a civil suit in that same investigation, setting up a civil trial with potentially major consequences for the Trump organization. Even there, though, Politico’s Josh Gerstein and Kyle Cheney argue that a settlement remains a real possibility, writing, “Pursuing the case through to completion could take years and there’s no guarantee that a judge will agree to grant all the relief the AG asked for.”

Only voters can truly take Trump down

If Trump is eventually criminally charged, it would take some time before a trial. And even if he’s eventually convicted, depending on what the charges actually are, it’s not clear he’d get a particularly harsh sentence.

All of that is to say that, if Trump wants to run for president again in 2024, it seems unlikely that the cases against him could remove him from the political scene entirely. (Some liberals are excited that one penalty for mishandling government documents is disqualification from “from holding any office under the United States,” but many experts believe that is unconstitutional as applied to the presidency, since qualifications for that office are set out in the Constitution.)

Instead, Trump’s political future will likely be determined at the ballot box, if he runs again — in the primary, and the general election.

There is a hope among some Trump skeptics, including in the GOP, that Gov. Ron DeSantis (R-FL) will run and prove a potent challenger. Perhaps that could happen, and perhaps Trump’s legal issues will help weaken his standing if GOP voters fear he’ll be an electoral loser.

Still, it’s far from clear how things will play out. As my colleague Zack Beauchamp recently wrote, Trump-esque candidates have done quite well in Republican primaries this year, and Trump continues to lead all national GOP primary polls, usually by large margins.

As for the general election, should Trump make it there, that’s murky too. President Biden recently said his “intention” is to run again but whether that’s a “firm decision” still “remains to be seen.”

He’d be 81 years old by election day, is not popular despite some recent improvement, and if he doesn’t run, it’s unclear which Democrat would succeed him. One might think that surely after January 6, Dobbs, and with criminal investigations hanging over his head, Trump is too damaged to win a general election. But as was demonstrated in 2016, the identity and political strength of the Democratic nominee will matter too.

Investigations and charges could well hurt Trump politically, though his die-hard loyalists will likely stick by him no matter what. But in either the primary and the general election, what would really be needed to beat him is a compelling alternative for voters to flock to instead. That’s the only way the Trump era in politics could really end.

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