"The Trump empire ... will fold like a stack of cards," says former prosecutor

Former DOJ and N.Y. prosecutor Kenneth McCallion: Trump's empire was "largely an organized crime organization"

By Chauncey DeVega

Senior Writer

Published October 3, 2023 5:45AM (EDT)

Former U.S. President Donald Trump attends the start of his civil fraud trial at New York State Supreme Court on October 02, 2023 in New York City. (Seth Wenig-Pool/Getty Images)
Former U.S. President Donald Trump attends the start of his civil fraud trial at New York State Supreme Court on October 02, 2023 in New York City. (Seth Wenig-Pool/Getty Images)

Republican frontrunner and presumptive 2024 presidential nominee Donald Trump faces as many as four upcoming criminal trials — but a civil case that could destroy his business in New York has leapt to the forefront this week.

To some degree, the lawsuit filed by New York Attorney General Letitia James alleging decades of fraudulent business practices has flown under the radar, perhaps because — unlike in the criminal cases Trump must face in New York, Florida, Georgia and Washington, D.C. — there is no possibility of criminal convictions or a prison sentence. 

But all that changed last week when New York Supreme Court Justice Arthur Engoron issued a summary judgment against Trump and his co-defendants, ruling that the evidence of fraud was so overwhelming that a full trial was not necessary. If that decision stands, Trump will likely lose control of many of his most high-profile businesses. As a practical matter, his supposedly successful real estate empire may well lie in ruins.

That could have all kinds of ripple effects. Trump may be deprived of easy access to funds he needs to pay his legal expenses, now estimated to be in the tens of millions of dollars. His brand and public persona will be severely damaged. Part of his power over the MAGA cult comes from his self-presentation as a billionaire and a shrewd, ruthless deal-maker.

Losing control of his trademark New York business ventures will likely cause Trump to suffer a severe narcissistic injury, whose long-term consequences are unpredictable. In the here and now, he is of course using the New York civil case to extract still more cash donations from his followers. This past weekend, Trump sent out this appeal for money:


According to news reports, I will be attending the civil trial in New York tomorrow where an anti-Trump judge is attempting to bring down the Trump Organization and financially break me.

Democrats are seeking to bring down the world-famous "Trump Tower" and impose what some are calling "the corporate death penalty" upon me.

This will be the FIRST TRIAL in the Democrats' string of witch hunts designed to destroy our 2024 presidential campaign.

The Left is hoping that if they can hurt me financially, that I will shut down my campaign and forever surrender our country to the radical Left Democrats and the Deep State.

They want to take away my freedom, my finances, and harass my family.

But they can never take away my resilience, my courage, and my determination to save this country.

And I'm certainly not alone in this fight…

…Millions of patriots have also declared that they will NEVER SURRENDER our country to the Left – and will peacefully defend our movement until Election Day 2024 when we win back the White House and MAKE AMERICA GREAT AGAIN!

Trump is a master propagandist, and a dictator in waiting. His claims in the above fundraising email, and more generally, are lies and gross distortions of facts and reality.

In an attempt to make better sense of Trump's New York civil case and what Justice Engoron's summary judgment means for his future criminal trials, America's democracy crisis and what may happen next, I recently spoke with longtime attorney and author Kenneth Foard McCallion. He is a former Justice Department prosecutor who also worked for the New York attorney general's office as a prosecutor on Trump-related racketeering cases. McCallion's books include the companion pieces "Profiles in Courage in the Trump Era" and "Profiles in Cowardice in the Trump Era," as well as "Treason & Betrayal: The Rise and Fall of Individual-1." This transcript has been lightly edited for length and clarity.

Given all the legal developments surrounding Trump in recent weeks and months, especially the summary judgment in New York, how are you feeling? How do you make sense of all this? 

I'm feeling better and more confident about the legal system, which has been a long time coming in bringing Trump to justice. But finally, things seem to be picking up pace, and the summary judgment motion and decision in New York was outstanding, really a model of clarity. The other Trump decisions, particularly the D.C. court decision by Judge Chutkan regarding her non-recusal, were also excellent. The decisions slapping down Trump and his lawyers for the frivolous motions that they've made have become essential elements in the protection of our modern judicial system in this country.  

The central premise of our legal system is that the law applies equally to everyone and does not exempt the rich and powerful. Trump probably should have been brought to justice a lot sooner, but better late than never. Trump's wealth and power certainly did give some prosecutors pause, and of course they wanted to make sure that they had a rock-solid case against him before filing their charges. The investigations have been far too long in coming, but now the moment of truth is upon us, and all the charges against Trump appear to be well grounded in fact and supported by the evidence.  

Trump is facing multiple legal challenges in both civil and criminal courts, and there is a window of opportunity to have these legal proceedings move forward. Hopefully Trump will be held accountable before next year's election season is in full bloom.

At what point do Trump's attorneys and other advisers tell him that he is in serious trouble and may go to prison? Has that already happened? 

Some of Trump's lawyers have tried to have that very conversation with him and were fired. Trump is basically now surrounded by a collection of legal sycophants who are telling him what he wants to hear so that they can continue to stay on this high-profile legal team. But there will come a point in time where Trump will be in the courtroom and a judge or a jury will be deciding his fate. I believe that one or more of these proceedings will lead to a guilty verdict and then sentencing. Trump is self-deluded to a large extent, but he most certainly is not stupid. Trump is like a fox who is ultimately cornered by the hounds, and only then will he will try and cut a deal to avoid spending time in prison.

"Trump is like a fox who [will be] ultimately cornered by the hounds. Only then will he will try and cut a deal to avoid spending time in prison."

Obviously, Trump, if convicted, would be sentenced to a gilded cage of sorts, be it in Mar-a-Lago or somewhere else. There are federal and state prisons for certain classes of inmates such as Trump. What Trump really fears is not so much being imprisoned, but the fear of conviction itself and public humiliation. He must have some awareness of the serious legal predicament he is in at this point, but he has to try to maintain a tough public facade for as long as he can. Trump will hold out until the last possible moment and then he will take a plea deal or some other arrangement with the prosecution. But at this point Trump's ego won't let him do it — at least for another six months or so. 

How would you assess the quality of the attorneys who are willing to work with Trump, given his reputation and behavior? What is their decision-making process like? I have to imagine that the best attorneys would want to avoid Trump because of the potential stain on their reputations. 

Trump's legal team is not, for the most part, an A-list team. The best available former prosecutors and defense lawyers have declined to join the Trump legal team because they fear that the aroma of corruption emanating from Trump will engulf them too and their reputations will be permanently tarnished. Some of Trump's prior counsel — obviously, Rudy Giuliani, and others — are immersed in their own legal problems now. The calculation being made by Trump's current legal team is that they will advise him professionally on the process, they will file motions and they will attempt to avoid being held professionally responsible, meaning either sanctioned or disbarred. They will not cross that line, although Trump will certainly want them to. But ultimately, Trump's attorneys will be in the limelight, and there's nothing wrong with being a credible and honest defense lawyer.

They will have to tell Trump, or it will become apparent to him, that he needs an exit strategy — and sooner rather than later. Trump and his team will try muddying the waters and engaging in legal kabuki theater for the next few months. But ultimately the day of reckoning will come in the New York proceedings, or in D.C. or Florida or Georgia, whichever may come first. 

Trump will be held responsible and convicted or criminally or civilly fined and held responsible, much like his corporations in New York, which are now going to be barred from doing business. In the end, the Trump empire, both the business as well as him personally, will fold like a stack of cards pretty quickly when the first jury returns its verdict against him. One of Trump's co-defendants in Georgia has already flipped and taken a guilty plea. More will follow. Trump's predicament will only get worse as time goes on. 

We need your help to stay independent

"Summary judgment" sounds like something out of a movie or TV show. What does that term actually mean as a practical matter? 

It is a very significant step in the civil legal process. Summary judgment means that the judge is deciding, and agreeing with the New York attorney general, that the case against Trump need not go to trial because the evidence on paper is so overwhelming that the legal issue of whether Trump and his companies acted irresponsibly is no longer a subject of reasonable factual dispute. The proper remedy is to have their certificates of incorporation revoked and to bar them from doing any further business in New York. In other words, you don't need a jury to decide a case when there are no real disputed issues of fact. When you have irrefutable evidence, like the attorney general has in New York regarding the factual claims, a judge can — and will — grant a summary judgment motion, which eliminates the need for a full jury trial.

The evidence presented to Justice Engoron conclusively showed that Trump's misrepresentations of fact about the value of his buildings and properties went far beyond mere negligence. Trump is a very detailed hands-on person with his businesses. He is a real estate developer. He is not someone who can claim ignorance. The evidence showed that Trump purposely misrepresented the numbers in order to grossly increase the amount of the loans that he was getting from the banks, but then undervalued the same properties for tax purposes. The attorney general of New York is in a very good place right now.  I would expect to see a very large award and judgment in favor of New York. I don't see any way that Trump, at this point, can avoid it. 

What explains Trump's ability to avoid consequences for decades when his alleged crimes were so obvious? 

The evidence has always been there, and some intrepid prosecutor could have taken this on much earlier. But these kinds of complex business crimes require a large amount of resources and expertise to investigate. The investigative journalists and forensic accounting experts deserve much credit for going through the laborious process of reviewing all the Trump Organization's public filings and tax returns. Then, when the banks were forced to turn over the loan applications from Trump to the attorney general, the New York County district attorney and others, the floodgates were opened. It was no longer just a question of tax fraud, since there was also evidence of substantial banking fraud. Things went downhill pretty fast for Trump after that. 

I come from the working class, so my first concern is about the regular folks who will be caught up in a court's decision to shut down Trump's businesses. What will happen to them? 

That's always a concern. I would expect that the likely procedure which has been followed in the past, and is followed by bankruptcy judges, is the appointment of a receiver who would protect the Trump assets and keep the payroll going while the assets are being liquidated in an orderly fashion. Hopefully, innocent employees will be protected in the process. 

What are some of the questions you want answered through these trials, given that you have faced Trump in court before as a prosecutor? I am very curious about the rumored connections, or in fact proven connections, between Trump's businesses and foreign money. 

I've written several books on the money laundering aspects of Trump's businesses. When Trump was basically banned by the large banks from any further loans and mortgages, this was right around the time when a lot of Russian and Eastern European money was looking for a home in the West. Therefore, it was an ideal time for Trump to start doing business with Russian oligarchs and others looking to park their cash in one or more of Trump's real estate projects. In fact, a significant percentage of the early purchases of the apartments in Trump Tower were cash deals involving Russian and Eastern European money looking for a safe place away from the prying eyes of the banking regulators.

"The full picture can [now] be seen, which is that the Trump Organization was largely an organized crime organization propped up by money of questionable origin."

Back then, large cash purchases of real estate in the U.S. were not as closely scrutinized when they did not involve large bank transfers. And Trump was more than happy to close on apartment deals with either bags of cash being transacted, or money orders or other financial instruments being used to circumvent the need for wire transfers and the red flags they would generate. The Russian uber-rich purchasers could actually use the apartment, or might not. That wasn't the point of the purchase. The primary objective was to hold the property for a few years and then sell it. What might be questionable or dirty money would then be converted into clean money in New York. So it was a classic money laundering operation. Trump did the same with apartment buildings in the Miami area as well.

Now that the actual business records of the Trump Organization's real estate transfers have finally come to light, the full picture can be seen, which is that the Trump Organization was largely an organized crime organization propped up by money of questionable origin, and that his real estate development projects were willingly used by Trump to facilitate huge money laundering operations.  

How would you assess Trump's criminal exposure from the civil fraud case in New York? 

Many executives do not have their fingerprints all over everything, and are able to use the "I didn't know what was going on" defense. Trump can't do that, since he is unable to distance himself from the criminal actions that took place on his watch. Trump compulsively scrutinized every detail and micromanaged every aspect of the real estate enterprises, especially when it came to the valuation of Trump Organization properties. Trump worked very hard at inflating his valuations — and reaped the financial benefits of that valuation fraud. But the downside for Trump is that his fingerprints are all over those valuations, and all over those loan applications. Trump is in a huge amount of trouble, and has a substantial amount of liability, both in the criminal and civil cases, which largely overlap. Civil proceedings would lead to monetary awards and judgments. The parallel criminal cases can also lead to fines, but also his inevitable incarceration, unless a deal is struck with the prosecutors before his sentencing. One or more of those prosecutions will be successful. It is just a question of time now, and the clock is ticking. 

What is this doing to Trump's ego and mind, to see his businesses destroyed? 

It is amazing to me that Trump has not had some type of emotional or mental breakdown by now. Trump certainly has to be given credit for his staying power. But there's a limit to every person, and even the strongest among us will eventually crack if tortured long enough, Trump will not be able to deny the reality of his perilous position much longer. The walls are quickly closing in on him. I would expect to see that, after another few months of public defiance, the pressure he is under will finally take its toll, both physically and psychically. Trump has a lot to worry about. He will keep making his public bombastic threats, but in the end he will not be able to act that way in court. Trump will have to sit there quietly and watch the evidence pile up against him, brick by brick, before a jury. 

How do you think Trump will behave during the trials? Will he act out? Will he turn them into a theatrical spectacle in order to cry victim and rally his followers? Or will it be an anticlimax where Trump is subdued and meek?

"After another few months of public defiance, the pressure Trump is under will finally take its toll, both physically and psychically."

Trump is not going to be able to disrupt the proceedings. If he does try to disrupt them, he will be put in another room or in a glass booth and forced to listen silently to the proceedings from there. It will not be "Trump theater" time. He will have to respect the rules or he will be physically removed from the proceedings. In any event, Trump's trials will be among the greatest legal spectacles in recorded history, but they won't be his spectacle. This will be a true inflection point for our country and all the world to see, as Trump is finally brought to justice. 

Where are we in the Trump saga, and what do you think comes next? 

Trump's fall from grace and power will be precipitous. The climax will be the trial and the jury verdict, which will come sooner rather than later. 

You seem much more hopeful than you were a few months ago. I am pleasantly surprised, even given the seriousness of these matters. 

I am feeling much more hopeful. Several months ago, when we began having our conversations, the Justice Department was floundering. It had been several years, with nothing happening with the investigation. Trump then shot himself in the foot by announcing that he was running for president. The following day a special counsel was appointed, and the rest is history. A real professional prosecutor went to work on Trump; there were no political prevarications. That move by the DOJ emboldened prosecutors on the state level. The prosecutors stepped up to the challenge and said, "Enough is enough." They now have mountains of evidence against Trump.

The congressional hearings and investigation of Jan. 6 were also very helpful. The select committee report really was a blueprint for at least one of the criminal indictments of Trump. Finally something was happening, and Congress deserves much of the credit for putting the prosecutors to shame and forcing them to finally do their jobs.

These prosecutors were just over-investigating and dithering on an extremely time-sensitive investigation. The 2024 election was approaching and the window of opportunity was rapidly closing. But now the wheels of justice are finally turning. Trump may never have to wear an orange jumpsuit with the "DOC" stamp on the back, but I'm quite optimistic that he will finally get his just deserts, in one form or another.  

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.

MORE FROM Chauncey DeVega

Related Topics ------------------------------------------

Donald Trump Election Fraud Interview Kenneth Mccallion New York Trump Crimes Trump Trials