How to prosecute Boss Trump: RICO
Donald Trump at opening ceremony for 2018 NATO summit. (Gints Ivuskans / Shutterstock.com)

Even folks who support Donald Trump might agree that the former president is a con artist, a master gaslighter and a shrewd racketeer. As I argue in my book "Criminology on Trump," the Houdini of white-collar crime and founder and CEO of the Trump Organization has effectively operated a criminal enterprise, beginning in 1980. He did so for the next 36 years before being elected president in November 2016. Throughout his presidency and afterward, Trump continued running, and even expanding, his criminal enterprise.

Trump's lifetime as an outlaw and a racketeer may finally be coming to an end after more than four decades of eluding the criminal law. He is currently encircled by at least six or seven significant civil or criminal investigations.. Most legal scholars or former U.S. prosecutors will likely approach these white-collar, corporate and state crimes evidently committed by Trump and his associates as disparate and unrelated litigating conflicts.

I would contend, however, that when Trump's fraudulent behavior is seen through the lenses of racketeering and the vantage point of a criminal enterprise, all his offenses or violations, whether civil or criminal, could be legally brought together and prosecuted under RICO, the Racketeer Influenced and Corrupt Organizations Act.

Just as Trump and his allies could be prosecuted for sedition, obstruction of justice and election racketeering, in a classic "hub and spoke" multi-pronged criminal conspiracy, the illegal activities at issue in each of these individual investigations or lawsuits can be viewed over time as spokes of the same criminal enterprise.

Trump is an outlaw, and I mean that literally. He habitually breaks laws of all kinds while remaining a free person. Trump is also a special type of outlaw, because he has no moral compass and no loyalty to anyone besides himself. In fact, he thinks and acts as an authentic sociopath.

Trump is not an outlaw out of negligence, incompetence or ignorance of the illegalities of the marketplace, the civil and criminal laws or the Constitution of the United States. Quite the contrary. Trump knows the subtle differences between what is lawfully right and what is unlawfully wrong. Even more important, Trump is an expert on criminal intent — and the lack thereof.

Moreover, Trump knows all about plausible deniability and has nurtured the idea that throughout his activities he was allegedly following or deferring to other people, such as lawyers, accountants, appraisers, etc. He also appreciates that the legal system is fluid in both theory and practice and is subject to valuation and interpretation. Finally, Trump understands that the administration of justice is malleable and subject to a high degree of internal and external discretionary power.

As a racketeer or mobster, Trump has always intermingled his legitimate affairs of business with the illegitimate affairs of organized crime. As he told a panel at the Museum of Television and Radio in Los Angeles in 2004, shortly after he signed his first contract to do "The Apprentice," he had been reluctant to sign on with the reality TV show because of all the mobsters that frequent his place of work: "I [didn't] want to have cameras all over my office, dealing with contractors, politicians, mobsters and everyone else I have to deal with in my business." More than a decade later as a presidential candidate, in one of his moments of public candor, he responded to a question about his friends in organized crime, "Winners team up with mobsters, losers don't."

Days after Donald Trump became the president-elect in 2016, without any admission of wrongdoing, he settled three civil lawsuits against the defunct Trump University for $25 million, two from California and one from New York, which had been folded into one class-action lawsuit.

One year after the Trump University settlement was approved by the court overseeing the Southern District of New York, Trump was ordered by the New York Supreme Court in November 2019 to pay "$2 million in damages for improperly using charitable assets to intervene in the 2016 presidential primaries and further his own political interests." That award was part of New York Attorney General Letitia James' lawsuit against the Donald J. Trump Foundation and its directors — Trump himself and his three adult children, Donald Jr., Ivanka and Eric.

As part of that settlement, the Trump Foundation was shut down and the funds that were illegally misused had to be restored. The foundation and its directors agreed to multiple stipulations in order to resolve the remaining claims in the lawsuit. Among these, Trump admitted to personally misusing funds at the Trump Foundation, and his adult children were subject to mandatory training requirements. Finally, if the Trump Organization tried to start a new charity, Trump agreed to restrictions on future charitable services and to ongoing reporting to the attorney general's office.

Flash forward from there to the 220-page complaint in the fraud lawsuit filed by James against Trump and those same three adult children last week in state Supreme Court. Trump is accused of padding his net worth by some $2 billion, and James is seeking at least $250 million in damages, the estimated value derived from the alleged fraud between 2010 and 2021.

Compared to $250 million, the Trump University and Trump Foundation fraud lawsuits now seem like chump change — especially because the resolution of this lawsuit may well mean the demise of the Trump Organization. Among other sanctions, James wants the Trump Organization to be placed under a stewardship and not to engage in any commercial real estate acquisitions for five years. She is also asking the court to ban Trump, Donald, Jr., Ivanka and Eric from ever again running a company based in New York.

When we recently learned that James' office had "rebuffed an offer" from Trump's attorneys to settle this civil lawsuit, I wanted to know — and still want to know — how much Trump was willing to pay (or do) to make the case go away, especially knowing that losing the case could mean the end of his family business.

At her news conference last Wednesday, James explained that the investigation not only "revealed that Donald Trump engaged in years of illegal conduct to inflate his worth, to deceive banks and the people of the great state of New York," but also uncovered evidence of potential criminal violations, including insurance, bank and tax fraud. James has shared her findings with both the IRS and the Southern District, where these cases could be pursued as criminal rather than civil matters.

Meanwhile, from the big-picture criminological perspective, we also know the Justice Department has been investigating the fraudulent Save America PAC — Trump's main fund-raising vehicle since he lost the 2020 election — which promotes baseless assertions about election fraud, and also played a role in trying to overturn the election and instigating the Jan. 6 assault on the Capitol.

There are also the ongoing DOJ criminal investigations into Trump's seditious conspiracy and obstruction of justice related to the fake electors scheme and failed coup that followed the 2020 election, as well as the stolen or "borrowed" classified documents recovered from Mar-a-Lago this summer.

As I opined in the Miami Herald last Wednesday, "When it comes to prosecuting Trump, it's not a matter of 'if,' but 'when'" the various lawsuits will materialize, and specifically what crimes he will be prosecuted for. After all, the racketeer in chief has literally engaged in decades of lawlessness and hundreds of potential violations spanning the years before, during and after his presidency.

I hedged my answers to these questions:

Unless the DOJ finds a way to combine the crimes of seditious conspiracy and obstruction of justice pertaining to Jan. 6 and the crimes of espionage and obstruction of justice pertaining to Mar-a-Lago into one complicated case — highly unlikely, if not impossible — then look for the Justice Department to either prosecute its classified-documents case in the spring of 2023 or its seditious conspiracy case in the winter of 2024.

Before the June and July select committee hearings on Jan. 6, and the subsequent scandal that emerged surrounding the classified documents found at Mar-a-Lago, I was concerned that Trump would once again most likely escape criminal prosecution. But once it became obvious that the DOJ almost certainly could not refrain from prosecuting the former president for his obvious crimes, secondary concerns kicked in.

I suspect we may see a hierarchy of discretionary prosecutions established, where the DOJ chooses to settle for one prosecution amid the myriad of possibilities, allowing Trump to escape accountability for most of his crimes. Even worse, there's the possibility that Trump would cut a deal to avoid any criminal trials and imprisonment.

This takes us back full circle to my unlikely proposition: The RICO statutes could and should be used as a means of bringing all the related civil and criminal charges from the various legal jurisdictions together, with the goal of prosecuting Donald Trump as a crime boss and his organization as a criminal enterprise.