Former federal prosecutor: A "day of reckoning" is coming for Trump — but he's not going to jail

Kenneth McCallion battled Trump in court — and says Merrick Garland has "overwhelming evidence" for conviction

By Chauncey DeVega

Senior Writer

Published September 19, 2022 6:00AM (EDT)

Donald Trump behind bars (Photo illustration by Salon/Getty Images)
Donald Trump behind bars (Photo illustration by Salon/Getty Images)

America's democracy crisis will not end anytime soon. Donald Trump and his acolytes in the Republican-fascist party continue to incite acts of right-wing violence, including terrorism, on a nationwide scale as part of their plan to end American democracy and replace it with authoritarianism and one-party rule. 

The Big Lie continues to spread across the United States. A majority of Republicans now subscribe to the repeatedly disproven theory that the 2020 Election was somehow illegitimate, that Trump is the "real" president and Joe Biden is a pretender and usurper. "MAGA" is American neofascism; it has fully conquered the Republican Party.

Even President Biden — who is committed to political moderation and remains eager to find "unity" with "traditional" Republicans for the good of the country — is finally issuing public warnings that today's Republican Party and the MAGA movement are basically enemy agents working to undermine America from within.

This moment of crisis demands bold, immediate leadership and collective action, not just from Biden and other leading Democrats but from rank-and file-Americans as well. But the urgency of stopping Trump and his forces is hamstrung by how the rule of law in a democracy operates slowly and justice often takes a very long time — if it ever does arrive.

Will Donald Trump eventually be prosecuted, convicted and then imprisoned for his apparent high crimes, which may include violating the Espionage Act? Attorney and author Kenneth Foard McCallion believes that the answer is probably no.

McCallion is a former Justice Department prosecutor who also worked for the New York State Attorney General's office as a prosecutor on Trump racketeering cases. As an assistant U.S. attorney and special assistant U.S. attorney, he focused on international fraud and counterintelligence cases that often involved Russian organized crime.

McCallion is also the author of several books, including "Profiles in Cowardice in the Trump Era" and "Treason & Betrayal: The Rise and Fall of Individual-1."

In this wide-ranging conversation, he offers his view that Donald Trump, along with his inner circle and his businesses, operate like an organized crime family. McCallion says these attributes and behavior help to explain Trump's affinity for foreign demagogues and other corrupt elements, including Eastern European and Russian criminal organizations.

McCallion reflects on his personal experience prosecuting Trump and his organizations, and the challenges of going up against a man he describes as a likely sociopath and a skilled pathological liar.

McCallion explains the approach that Merrick Garland and the Department of Justice will likely take in prosecuting Trump for the government documents he stored at Mar-a-Lago and the events of Jan. 6. Any such prosecution will require both overwhelming irrefutable evidence and a simple and direct story to tell a jury about Trump's misdeeds. McCallion also says that contrary to some media reports, Trump can definitely still be prosecuted even if he announces he is running for president.

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Toward the end of this conversation, McCallion outlines a likely scenario for the final disposition of such a prosecution. He believes that Trump may be brought down by a litany of civil lawsuits that will cripple him financially, not by a high-profile criminal case in which the former president is "perp-walked" in handcuffs and then sent to prison.   

This conversation has been edited for clarity and length.

How are you feeling, given everything that's happening? With your expertise and experience, how do you process all these events? What are you seeing?

The next book I'm working on is actually titled "Civil War II," but the ending is yet to be written. Over the last few weeks, I've been shocked at the extent of what we are learning about the Espionage Act and the hiding of secret government documents by Trump at Mar-a-Lago.

Why did he do that? I don't know. But I do believe that kind of hubris, and that inability to really let go of the mantel of the presidency, may in the end be his undoing. Trump has certainly left himself open for being prosecuted for serious crimes related to espionage and various other things.

That kind of hubris, and that inability to really let go of the mantel of the presidency, may in the end be Donald Trump's undoing.

There are encouraging signs. I was quite delighted that a friend and former mentor of mine, Raymond Dearie, who is a retired district judge from the Eastern District of New York, where I was in the U.S. attorney's office, will most likely be the special master [reviewing the Mar-a-Lago documents]. I was worried that the Justice Department and the attorney general had dozed off and napped for several months, but it appears they are hard at work now.

The Jan. 6 committee really gave the Department of Justice a lot of impetus and momentum. There are also good indications that justice may actually be done with the New York attorney general's [civil] case, and perhaps the Manhattan DA's [criminal] case too.

Is there actually anything shocking about any of the things Trump and his allies have done? Donald Trump has been a public criminal for decades. Jan. 6 was in many ways a predictable event and was announced beforehand. My point of view is pretty simple. We know who Donald Trump is. There is a long pattern of his evil behavior. What is "shocking" about any of this? He is utterly predictable.

Those of us who know Donald Trump also understand that he is probably beyond reformation and may actually be psychopathic. However, I think it's important to say that Donald Trump's behavior and presidency, and what he continues to do, has been a shock to the democratic system. We cannot lose the capacity to be outraged at Trump's behavior. We need to have that sense of outrage in order to protect the country's democratic institutions, which are under attack right now.

Where are the consequences for Donald Trump and his apparent criminal acts and other wrongdoing?

I do believe that the Justice Department probably should have moved much faster with the Mar-a-Lago documents, given that we are entering an election season. However, we need to uphold the principle that no man is above the law no matter what time of year it may be, political happenings or not.

It's never a convenient season for the rich and powerful to be held accountable. It's almost a perfect storm at this point between the Department of Justice investigation, the New York attorney general's investigation and various civil suits against Trump. The pot is boiling now in several different respects. One or more of these investigations will almost certainly lead to the undoing of the Trump Organization.

There is also significant personal liability for Donald Trump for the obstruction of justice and for a long list of crimes that are now being investigated. Attorney General Garland and the Justice Department really have to follow through this investigation to its logical conclusion. The evidence is overwhelming. Any honest prosecutor is not going to want to say, "I pulled my punches," or, "I let Donald Trump go just because he's the former president."

You have a lot of experience with Donald Trump. You faced him and his organization as a prosecutor. When you saw his candidacy in 2016 and then saw him win the election, what were you most afraid of?

I worked with the organized crime section of the Justice Department when I went up against Donald Trump and his lawyer, Roy Cohn. We were primarily investigating labor racketeering, involving unions that were dominated by various organized crime families, including the Teamsters and others. In our investigation, we found that Donald Trump and some other developers used their connections with organized crime to get immunity from strikes by entering into corrupt contracts — promising "no-show" jobs, for example. These corrupt contracts gave Trump and others a competitive advantage.

It quickly occurred to us, and I think it's apparent to all of us now, that Trump and his organization are just another organized crime family. They try to maintain the code of silence, but that hasn't been entirely successful. There is a complete disregard for the law. In terms of fraudulent intent, even if they could have made money honestly, Trump and his people — like many organized crime-controlled companies — try to cut corners.

It quickly occurred to us [in the DOJ], and I think it's apparent to all of us now, that Trump and his organization are just another organized crime family.

They take advantage of their connections with organized crime and their connections with corrupt foreign leaders, such as Putin. Russian organized crime always had a very close connection with the Trump organization. After Trump's casinos in Atlantic City went under and the banks started pulling back their financing, Trump and his organization and his development projects have been financed through shady money from Eastern Europe and Russia, from the oligarchs.

They have been Trump's lifeblood for his financing. His worldview has always been oriented towards the countries where oligarchs and dirty money are prevalent. Donald Trump was dead set on attempting to convert the United States into a replica, to some extent, of the antidemocratic, authoritarian, oligarchical systems we see in Hungary, Russia and various other parts of Eastern Europe.

Given your experience with Trump, what did the news media and the American public fail to understand about this man? Or perhaps, what were they afraid to acknowledge?

Many people naively thought that Trump, despite his outlandish behavior, was just being hyperbolic and not seriously intentioned. What they didn't realize is that Trump bought into his own nonsensical worldview. Millions of adoring people worship Donald Trump — as he has said, he really could walk down Fifth Avenue and shoot somebody, and his followers would still love him.

Did Trump really believe that the election was stolen from him in 2020? The frightening thing is that Trump has not only convinced many of his followers of that, he has probably convinced himself of that, which makes him the most dangerous kind of dictator or autocrat. He has lost all sense of any ability to pull back from the brink. Donald Trump is not restrained by any of the guardrails of our normal democratic processes. He and Steve Bannon and the rest of that inner circle have brought the United States to somewhere quite different than this country's ever been before.

But in the end, I do believe that the pendulum will swing back, much as it did with, for example, Sen. Joe McCarthy in the 1950s with his Red scare. I truly think the wheel will turn and we're not going to go over the cliff.

Where does that hope and belief come from? Trump has escaped responsibility for decades.

Trump has lost all sense of any ability to pull back from the brink. He is not restrained by any of the guardrails of our normal democratic processes.

As bad as things are now, and as divided as the country is, there have been other times in our past where we have faced great difficulties. Yet somehow we survived the turmoil and the storms and got to a better place. I think it's a constant struggle. We are in the midst of one of those fundamental struggles, with Trump and his movement and the assault on democracy and the rule of law.

As you said, Merrick Garland could have moved earlier. I'm one of the people who wondered what the hell he was waiting for: Lock him up! Help me understand what the law requires, versus what political expediency demands.

The Department of Justice has to be thorough here. When I was with the Department of Justice, as a young prosecutor, I'd be anxious to bring organized crime figures to trial. But like Trump, many heads of crime families delegate the dirty work to other people. So to nail Trump and hold him responsible beyond a reasonable doubt, you really don't want to leave anything to chance. You need overwhelming evidence.

I think we're really getting to the point where we have that critical mass, especially after the Mar-a-Lago search and the documents obtained there. That was a fumble by Trump on the five-yard line. He might well have gotten away with not facing a criminal indictment for all he had done before that, but he had the audacity and the hubris to take top secret government documents with him after leaving office.

People of ambition and of monumental ego, like Donald Trump, have blind spots. Trump is bringing himself down. What I really fear is that a smarter Trump-like figure, maybe like Ron DeSantis, could actually do a lot more damage than Donald Trump.

In my view, Trump is a criminal genius. When you go up against somebody like that in court, how do you prepare?

When I did my cases, it was much like building a brick house. You have to do it from the foundation up, but there's always a moment when a prosecutor has butterflies in his stomach. When you have to cross-examine a Trump-like figure or the head of an organized crime family or someone of that type more generally, there is anxiety even when you have overwhelming evidence against them

Remember, these people are pathological liars. I'm sure that Donald Trump, if he was given a polygraph, would pass with flying colors. It's a matter of experience, plus a natural sociopathic ability to lie.

Trump's had a lot of experience with lying and the courts. He has some pretty good counsel, but I think over the next few months that most of the documents taken from Mar-a-Lago are going to be turned back over to the Justice Department. We'll see the wheels of justice continue at that point. Letitia James, the attorney general in New York, will get a very solid result against the Trump Organization, as will the DA in Manhattan, Alvin Bragg. Those cases are not against Trump personally, but against his organization. His chief lieutenants will be brought down and face very substantial fines for their economic and financial sleight of hand.

What do you think the approach to prosecuting Trump will be? The evidence seems overwhelming, but nothing's decided until you're in court.

It has to be laid out very simply for the jurors. It's basically two plus two equals four. You have Trump with these documents, some of them in a basement, but some of these top-secret documents were found by the FBI next to his passport in a private part of his desk. These documents were close to him every day. Trump certainly had knowledge and awareness of the documents; he knew they were top secret. He knew they had been taken from the White House. I think that you would just put it to a jury that you don't leave your common sense and good reason at the door when you are sworn in as a juror.

It's basically two plus two equals four. ... Trump certainly had knowledge and awareness of the documents; he knew they were top secret. He knew they had been taken from the White House.

We spend our entire lives evaluating people, separating truths from falsehoods and connecting the dots. It's much the same way that organized crime figures were brought down. Al Capone, for example, was put in prison not for the many murders he committed, but for tax fraud. With Trump, it will be the same thing. It's a very simple story you can tell. With top secret documents, the story tells itself.

What do you think Trump was doing with the top secret and other highly classified documents?

Actually, on this point, I give Trump somewhat the benefit of the doubt. I think his ego would not let him leave all the trappings of power back in the White House. In his mind, he had to take something. Now, did he foreclose the issue of selling the documents for money if necessary, or using them for political purposes? Those avenues were available to him as well, but I doubt Trump had a clear-cut plan. He knew they were top secret documents and he took them. It is not a requirement that the prosecution establish his intent, other than an intent and a willfulness to keep top secret documents out of the government archives and in his own personal possession. Mar-a-Lago is a place that is crawling with potential spies, Chinese and otherwise.

Donald Trump engaged in a flagrant violation of his national duty. That willfulness and intent and recklessness is, I believe, sufficient for a criminal conviction.

So how do you approach finding a jury where you won't have one person who is going to nullify in Trump's favor. That's the practical problem. Is it possible to find an honest jury that is not tainted by Trumpists?

In jury selection, I always tell a client: You're never going to get the jury that you want, but you want a jury that's going to call the balls and strikes the way they really are. You don't want jurors who are dead set against you and supporting the opposition. Through your jury challenges, you can just weed out those people as best you can. You have to keep in mind that a lot of people underestimate jurors. For example, in the Paul Manafort trial some of those jurors were actually predisposed to be favorable to Donald Trump's worldview. Yet they found that Paul Manafort had violated the law on several counts and should be held liable under the criminal laws.

The jury system is a risky one. It's somewhat of a mystery, even to me, with all my decades of experience.  But by and large, the guilty are convicted and the innocent can go free in our system, with some notable exceptions of course. Some jurors are reached by external forces, organized crime, political or otherwise. But by and large, I think the system is more or less equitable. It will be a great day for the justice system when Trump and some of his chief lieutenants are held accountable.

How do you explain to the average person what a RICO case is? How would you approach that type of prosecution in the case of Trump?

The racketeering laws are extremely flexible. It is much like describing an organized crime family that has a certain structure. The person at the top is calling the shots and the other members may not know what each of the others are doing. However, they subscribe to and agree with the overarching principles and goals of the organized crime family. In this case, that is to keep Donald Trump and his minions in power, to hold onto the White House through means fair and foul — primarily foul. Trump and his minions reject the basic norms of democracy.

They've used mail and wire fraud and engaged in various other violations of federal and state law over an extended period of time as well. That is really the informal definition of a racketeering conspiracy. Trump and his minions have engaged in that behavior.

But I think that Garland and the Justice Department may well steer clear of an extremely complex RICO-type case and just go with some very pointed, targeted violations. These violations are clear: espionage and various other laws. There are the facts and evidence to support racketeering and conspiracy charges. But the problem is that the more you complexify a case, the more likely it is to run on for weeks. Jurors are human beings; you can start losing some of them.

In my opinion, the Garland Justice Department learned a lot from the Jan. 6 committee hearings. It's probably going to follow that more simplified, direct, powerful route in bringing its prosecutions.

What can the Department of Justice prove conclusively about Donald Trump in order to hold him criminally accountable? It is easy to list all of Trump's acts of perfidy, immortality and wrongdoing, but that may not be enough to prosecute and convict him. It may all be wrong, but is it clearly illegal? 

I think the Justice Department is going to focus on two scenarios. One will be the events leading up to Jan. 6. The coordinating and fundraising, the attack on the Capitol, the attempted election subversion and related happenings. The Justice Department has built a pretty strong case that Trump was the lead instigator of that demonstration and the assault on Congress. The other focus will be on the Espionage Act and related charges regarding the documents at Mar-a-Lago.

What does the Department of Justice do if and when Trump announces that he is running for president? Do they have to hold off for another four years if he wins?

It is conceivable that Donald Trump might do some time. But I would not put the odds on him being handcuffed and perp-walked, with the press photographing him.

If the Department of Justice gets an indictment, it should happen sometime later this year. They wouldn't do it in the window from now to November, the political season, but maybe the end of this year or early next year. One of the things people don't realize, and maybe Trump doesn't realize, is that once he declares for the presidency he will not have the Republican National Committee and other groups paying for his legal defense at that particular point. Trump is an extremely cheap individual who will have to pay out of pocket for millions of dollars in legal fees.

The Justice Department will not stop or pause, except for the political season in the midterms. They will not stand down just because Trump is a presidential candidate. Whether he is a presidential candidate or not, Trump and his supporters are still going to say it's a political prosecution.

The best defense for Trump is to attack the prosecutors. The prosecutors have to take a few punches and be vilified in the press, as they were after the Mar-a-Lago search. Although he waited too long, Merrick Garland did hold a press conference, as well he should have. The Justice Department is not a punching bag. It's entitled to protect itself and its reputation.

Many observers are claiming that if Trump announces his candidacy, the Department of Justice will not proceed with prosecuting him because of some type of informal rule or guideline. Garland and the DOJ will pause everything at that point, and perhaps drop it entirely, because to prosecute a presidential candidate would look too "political."

Absolutely not. If they did such a thing, they would be violating their oaths and professional ethics. The rest of the country would be wondering why there's one set of laws for us and another set of law for Trump and his kind.

What happens if Donald Trump is prosecuted and not convicted? What are the next steps, as a legal matter?

I can see the O.J. Simpson scenario playing out here. O.J. beat the criminal rap, but he was done in by the civil cases. Although there's a focus on the Department of Justice investigation, there are a host of civil cases out there against Trump. Trump will be involved in litigation for years, whether or not he beats a criminal rap.

Many people with public platforms keep proclaiming that Donald Trump is going to jail. That it's inevitable and we are eventually going to see Trump do a perp walk. Is he going to jail, in any version of this universe? What are the real range of practical or realistic consequences for him?

If I were a betting man, I would not put the odds on Donald Trump being handcuffed and perp-walked with the press photographing him on the way to a jail cell. The Justice Department has to pursue the investigation to an indictment and then prosecute it. As you know, not every case reaches trial. There is always the possibility of plea deals. Yes, it is conceivable that Donald Trump might do some time. But it's more likely that there would be some sort of plea deal to some of these offenses, in order for Trump to avoid a jail sentence. Trump would have to allow himself to actually admit guilt for some of these crimes.

In the real world, yes, some of the guilty do escape justice. But with the focus on Trump and the evidence that's available, I believe there will be a day of reckoning. Exactly what the consequences are after that is anybody's guess.

Here is my best-case scenario. Donald Trump takes a plea offer. There are some fines and he agrees to not run for public office again. But he then continues to be a public menace, agitating for right-wing terrorism, threatening democracy, repeating Jan. 6 and inciting other unrest. But what message is sent if the Department of Justice makes a deal with him? If Trump is not convicted and put in jail, what does that mean for the future of the country?

Keeping Trump from the White House again is a real benefit to the country. He'd have to agree to that in any plea deal. Trump would have to explicitly promise not to run for public office again. Will he continue to agitate and attempt to grab press headlines? Of course, but the Republican Party and his followers, at some point, have to move on. Donald Trump has had his moment. In the end, the country will get past Donald Trump.


By Chauncey DeVega

Chauncey DeVega is a senior politics writer for Salon. His essays can also be found at He also hosts a weekly podcast, The Chauncey DeVega Show. Chauncey can be followed on Twitter and Facebook.

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