Will America Send Donald Trump to Jail?

A serious look at whether or not President Trump will be become convicted felon Trump.

A few decades ago in 2018, huge swaths of #Resistance Twitter had adorned their handles with a “Not Individual-1” moniker. The reference was to President Trump’s description in the indictment of his former bagman, Michael Cohen. Cohen’s indictment fingered Trump as an accomplice in the crime (illegal campaign contributions), and officially made the President an un-indicted co-conspirator in a federal crime.

The reason we had to describe Trump as an “un-indicted” co-conspirator is that - as President - he literally could not be indicted at the time. But that changes on January 20, 2021, when Joe Biden will be sworn in as the 46th President of the United States and Donald Trump goes back to being a toilet brush salesman (or whatever he did before).

The big question on everyone’s mind is what happens to Teflon Don when he loses his teflon? Jonathan Mahler in the New York Times Magazine tackled this question over the weekend. His entire analysis is sober, and grounded in the facts. If you want a tl;dr version, many of the people he spoke with threw cold water on the possibility of a federal prosecution coming for Trump:

As president, Trump cavalierly called for the imprisonment of political opponents, shattering a longstanding democratic norm. This is not a precedent to follow lightly. Presidents have historically gone out of their way to avoid using the power of the office to pursue their political rivals. When President George H.W. Bush pardoned six Reagan White House officials who were involved in the Iran-contra affair, he warned of “a profoundly troubling development in the political and legal climate of our country: the criminalization of policy differences.” Bush was sparing members of his own party. President Obama created what is perhaps an even more relevant precedent for Biden by choosing not to prosecute members of the George W. Bush administration who had authorized the unlawful torture of detainees; his nominee for attorney general, Eric Holder, used the very same phrase — the criminalization of policy differences — when the issue came up during his House confirmation hearings. Over the summer, I asked David Cole, the national legal director of the American Civil Liberties Union, what he thought would happen to Trump if he lost the election. “My gut is that you’re very unlikely to see a federal prosecution,” he told me. “For me, the real accountability will be on Nov. 3, if he is sent packing from the White House.” It was a sentiment that I heard from a lot of legal thinkers and former government officials in the months leading up to the election: The visions of Donald Trump in an orange jumpsuit were more fantasy than reality (my emphasis). 

Mahler goes through all the downsides of pursuing what would be an explosive and damaging prosecution of a former president. He highlights how such actions could undermine the reputation of the Department of Justice, which is already heavily damaged thanks to Bill Barr. Mahler also suggests that criminality is part of Trump’s nature, and that it was there before he became President:

[Y]ou have to first look back on the entire Trump presidency in a different way — one that sees his possibly criminal conduct not as a byproduct of the pursuit of a political agenda but as a central, self-perpetuating feature of his tenure. In this light, Trump’s potential criminality becomes a kind of throughline, the dots that connect his life as a businessman to his entry into politics and then onward across his four years as president. One potentially illegal act led Trump to the next: from his law-bending moves as a businessman, to his questionable campaign-finance practices, to his willingness to interfere with investigations into his conduct, to his acts of public corruption and, finally, to the seemingly illegal abuse of the powers of his office in order to remain in office.

Mahler’s whole piece is really excellent and exhaustive. And it is also great in the sense that it addresses all the anti-Trump fantasies and is not shy about criticizing them. You may, in fact, walk away from the piece thinking that a prosecution of Trump would be a bad idea. Still, Mahler concludes with this:

In that sense, the problem that Trump poses for Biden may also present an opportunity, a chance to repair more than just the damage of the last four years. To begin with, this may require recognizing that when a president brazenly flouts the law, electoral defeat might not be enough of a punishment. “There’s a mind-set that we need to reset,” Stephen Vladeck, a constitutional law professor at the University of Texas, told me. “Breaking the law is not a political difference.” It might also require recognizing that to really move on from Trump, “healing” may have to mean something fundamentally different from what it has in the past — and that without accountability, it may in fact be impossible.

Reading this immediately makes me think of another public figure who has never been held accountable for his actions. Yesterday, New York’s Governor Andrew Cuomo gave the nation his best Trump impression in the form of a press conference, where he publicly berated a journalist from the Wall Street Journal for asking a question about the “confusion” Cuomo’s new COVID-19 restrictions would create.

More than one journalist noted that Cuomo targeting the Wall Street Journal seemed to be highly coincidental:

Twitter avatar for @TweetBenMaxBen Max @TweetBenMax
there's actually a tell in here - "follow the facts" - that says this outburst at a WSJ reporter was in part about the bigger picture coverage of Cuomo, including this WSJ piece:

southpaw @nycsouthpaw

If I squint, I think kinda understand: his point is that the state law governs this decision and it’s not his personal fiat, but jeez there’s not much grace in the message. https://t.co/x9vA9WbCSx

The aforementioned piece exhaustively highlights the disaster of Cuomo’s COVID-19 response:

Within days, Mr. Cuomo’s team approved an order from the state’s health department that said nursing homes couldn’t refuse to admit patients simply because they had tested positive. The order would become one of the most controversial decisions of the response.

I’m bringing up Cuomo’s insane COVID-19 decisions because I think it is a good example of what happens when someone in power isn’t held to account. Cuomo’s office clearly steered COVID-19 patients into nursing homes and when he was criticized for it, his office removed the order from the Governor’s website. Call me crazy, but using the power of your office to avoid accountability for your actions sounds a little…Trumpian?

Part of the reason Cuomo feels comfortable enough to do this is because of a media apparatus that somehow thinks it’s O.K. to have the Brothers Cuomo yucking it up on cable news every night, despite the fact that the younger Cuomo has an obligation as a journalist to investigate his brother (unless CNN, much like Fox News, just has opinion shows in the evening).

Another reason Cuomo feels comfortable is because he has never been held to account for the corruption that has stemmed from his office. In a detailed piece from 2016, Jeffrey Toobin (peace be upon him) went over not only the primary scandal at that time - the sentencing of a myriad of Cuomo aides (including one of his closest friends) for corruption related to a project in Buffalo - but also Cuomo’s ability to shut down investigations into his own corruption, namely the Moreland Commission. Perhaps one of the differences between Cuomo and Trump is that while Trump was unable to derail the Special Counsel’s investigation, Cuomo was actually successful. Much like Trump, Cuomo seems to have a penchant for surrounding himself with people who eventually get indicted, but always seems to avoid indictment himself (although Preet Bharara and the Southern District of New York came close).

Cuomo’s mistakes with COVID-19 are what happens when a leader is never held accountable to (or by) the public. Trump has likely felt that way his entire life; as Mahler outlines in his piece, Trump has avoided prosecution for his various scams like Trump University and maybe even Trump Steaks, which were apparently so bad it should have been a felony to sell them. Without payment for his crimes in office, Trump may well feel free enough to commit them again once he leaves. The other major factor is the (probably safe) assumption that Trump’s successors may take a lesson from him.

The obvious recourse would be to teach those successors and Trump himself a new lesson. A few Jackals back I said this (we also probably avoided the nightmare scenario I laid out in that piece; go America!):

The way I always like to frame answers to the question, “Will Trump be prosecuted after he leaves office?” is: It is true that Trump is legally vulnerable right now. What is also true is:

  1. Federal prosecutors are extremely risk-adverse. State prosecutors are a little more loosey-goosey, and will take a risk on a weird legal theory if they think they can convince a jury. Federal prosecutors generally only prosecute when they are positive they can win. 

  2. Indicting a former president is the opposite of being risk-adverse.

I want to clarify: A prediction of what I think will happen is not outlining what I think should happen. Prosecuting Trump for his many crimes committed in office, on the campaign trail, and in his private capacity as a citizen may actually be necessary to preserve some sort of respect for the rule of law.

And then let’s indict Cuomo too.