Whenever one writes about Donald Trump, he or she has to recognize that Donald Trump is a very polarizing force. To many on the so-called right, he is a demigod, a much better president than Abraham Lincoln or Ronald Reagan. To many right-wing Christians he has done more for them than Christ. To the left, Trump is the personification of evil, a traitor who sought to undermine democracy and work with Vladimir Putin, and a fraud. There is no middle ground when it comes to Donald Trump. I do not intend to become involved in this debate. Rather, I would like to simply try to explain some of the legal processes in which Donald Trump now finds himself in.

It has a been a busy couple of weeks for the former-President. When I first started this article, I intended to focus on the former-President’s decision in a deposition to take the Fifth Amendment on the grounds that his answers might incriminate him nearly 450 time. Then, the very next day, the FBI raided his residence seizing multiple boxes of evidence, so I had to change the article to add this additional significant legal row. Then just as I was finishing the article once again, word came out that the Trump Organization’s former CFO, Allen Weisselberg, was going to plead guilty in another criminal case and testify against the Trump Organization. But what do these events really mean? As someone who has practiced federal criminal law for decades as both a prosecutor and a defense attorney, I would like to take a few minutes and talk about what we know, and, just as importantly, what we do not know about these cases.

Before discussing the events of the past two weeks, however, I would like to go back to January 7th, 1998, and the Bill Clinton/Monica Lewinsky Affair. Clinton had already been sued by Paula Jones for sexual harassment, and evidence of a sexual relationship between the President and an intern had reached Ms. Jones’ counsel. In order to forestall the issue, Clinton’s attorneys had Ms. Lewinsky sign an affidavit stating that there had never been a sexual relationship between her and the President. This act constituted perjury on Ms. Lewinsky’s part and subordination of perjury on the part of the President. Both knew that affidavit was false. Then days later, President Clinton testified in a civil deposition under oath and lied about the affair. At that point, Clinton added another federal felony—perjury—to the subordination of perjury he had committed less than two weeks before. By the end of the month, media outlets began covering the story leading to one of Clinton’s most quoted lines: “I did not have sexual relations with that woman, Ms. Lewinsky”. It was a lie, but it was not under oath and therefore was not a crime.

I must confess to a certain amount or naivete at the time. I was a First Assistant District Attorney prosecuting cases, and I saw Clinton’s issues as criminal issues. To me, the evidence of perjury and subordination of perjury was overwhelming, and a criminal conviction, or at least impeachment, seemed imminent. When Clinton huddled with pollsters and political consultants, I thought he was making a big mistake. It seemed to me that he should be retaining and working with the best lawyers available. As it turned out, I was wrong. I also thought that Presidents should be held to a higher, not a lower, standard than everyone else. Ordinarily, people who commit perjury are tried, sentenced, and sent to prison. Clinton, however, was given the pass.

There are therefore different rules for former Presidents. Since I do not understand those rules, I cannot predict how they will play out with former-President Trump. It is clear that he has legions of followers more loyal to him than to American democracy or truth. I used to think that many of these followers were misled and that once they understood the truth, they would do the right thing. I now believe that they now have no love for or commitment to democracy. I think that many of his followers would prefer a Trumpian dictatorship to a democracy where the majority of voters determines who is in charge. Can these followers stifle the rule of law? Maybe.

A Road Map of Current Legal Issues

I am a white-collar criminal defense lawyer, and I have represented many individuals with significant legal issues. Almost always, these issues stem from a certain set of facts—a securities fraud scheme, for example, where there are multiple alleged victims where the SEC, the FBI, state regulator authority, and state criminal prosecutors are all investigating the same basic scheme. These case are challenging to be sure, but in the case of Donald Trump, there are several different investigations looking into entirely unrelated alleged criminal activity. Some of the investigations involve:

  • The District Attorney of Manhattan, New York, investigation into the Trump Organization for state tax fraud and banking fraud.
  • The Fulton County, Georgia, District Attorney investigation of Trump for interference with the electoral processes in Georgia.
  • Attorney General of the District of Columbia criminal investigation into incitement to riot.
  • West Chester County, New York, investigation into whether the Trump Organization engaged in fraud or made criminally false statements in the purchase of a property.
  • Department of Justice investigation into the mishandling of classified information.

In addition to these known frauds, there are also suspected investigations into Trump’s role in the attack on the Capital on January 6th, 2021, and the alleged conspiracy to commit wire fraud by paying hush money to Stormy Daniels and others. There are also at least a dozen civil suits swirling around he former-President, many of which allege fraud or sexual harassment. There may well be other criminal investigations that have yet to surface.

The analysis of each of these cases is complex, but it is necessary to understand that there are multiple, unrelated criminal investigations looking into a variety of different activities. These cases, however, are largely unconnected. Therefore, different actions are being undertaken by different prosecutors all of the time. We are seeing only glimpses into actual investigations.

The Fifth Amendment

The Fifth Amendment to the U. S. Constitution protects an individual from compelled self-incrimination (…compelled in any criminal case to be a witness against himself). It may only be asserted when a person reasonably believes that the answers he or she would give would incriminate him or her. There are consequences to asserting the Fifth Amendment in a civil case. First, it looks bad. The Fifth Amendment used to be viewed as the refuge for mobsters and other criminals. Second, invoking the Fifth Amendment in a civil case creates an “adverse inference”, meaning that a jury or judge can use the fact that you asserted the Fifth Amendment against you. For Donald Trump, it means he will lose the fraud case brought by the Attorney General of New York.

Does the invocation of the Fifth Amendment mean the person asserting it is “guilty”? The answer is no. To begin with, the fact that an answer to a question might be incriminating does not mean that the person giving an answer is guilty. For example, in a murder investigation, an interrogator might ask: “Isn’t it true that you were having an affair?” The question might suggest a motive for murder, and a truthful answer could be used against the person being questioned (if he or she is in fact having an affair). The fact that the person has a motive for murder, however, does not mean the person committed the murder. In such a case, an innocent person might very well assert the Fifth Amendment.

It is important to note that in our criminal justice system, everyone charged with a crime is presumed to be not guilty and can only be found guilty if the government can prove his or her guilt beyond a reasonable doubt. We do not have an inquisitorial system where the government can haul someone in before a grand jury and force them to incriminate themselves. The framers of the Constitution sought first to protect this right with the passage of the Fifth Amendment.

Most often, however, in the types of investigations that Trump faces, one would expect that he would not assert the Fifth Amendment lightly. In most cases, witnesses assert the Fifth Amendment because they are guilty, and most people think like the pre-2020 Trump used to think: “If you’re innocent, why are you taking the Fifth Amendment?” Most innocent people do want to avoid the reputational damage associated with taking the Fifth Amendment.

This may be an instance where Trump is calculating that his attacks on the criminal justice system and his appeals to conspiracy theories will overcome normal criminal processes. If he blames the problems on “the deep state” or “the fake news” perhaps he will be able to survive and prosper. It is reminiscent of Hillary Clinton blaming her husband’s legal woes on a “vast right-wing conspiracy”.

The Search of Mar-A-Lago

To many of the right, the search of Trump’s residence means war. To many on the left, it is conclusive evidence of Trump’s guilt. It should be noted that there is nothing in the Constitution or the laws of the United States that prevents a former-President from criminal investigation or prosecution. In 1973, Spiro Agnew, the former Vice-President of the United States was convicted of a variety of offenses and went to prison. In 1807, Aaron Burr, the third Vice-President of the United States was tried for treason but acquitted. Dennis Hastert, the Speaker of the House of Representatives, was convicted in 2007 of paying hush money to the family of a boy he had molested and sentenced to prison. A former-president had no greater privilege than these other high officials, and it should not come as a shock that there are investigations into a former-president’s conduct.

The hysteria evidenced by some Trump supporters is surprising. At this time, there is not much we know about the search. A judge released the warrant and the search inventory. The warrant is the order from the court authorizing the search. It simply identified the place to be searched and the items to be searched for. It also contains the court’s finding of probable cause, but it does not identify the facts the judge relied upon in issuing the warrant. The search warrant inventory identifies the items seized but nothing more. The affidavit, which has not been unsealed, would be where the details describing the investigation and its findings would be located. Affidavits normally remain sealed until a defendant has been indicted and sometimes are not released even then. In this case, however, the judge has ordered the government to produce a redacted version of the search warrant affidavit. We do not know how this will be resolved yet.

Furthermore, the search of a defendant or his or her residence does not portend the filing of charges. Often times, search warrants are issued, searches are completed, and no charges are filed. This can be because nothing of evidentiary value was recovered. It can be that even with the evidence recovered, there is simply not enough to indict. Over the course of my career, including twice in the past year, I have been involved in many searches that did not result in charges. There are also cases where nothing is found in a search, but the individual searched is indicted anyhow. Search warrants are simply one of many investigative tools the DOJ and the FBI have at their disposal.

What Can we Glean from the Search Warrant?

At this point, the only thing we can say from the investigation is that the former President and others are under investigations for violations of federal law, specifically Obstruction of Justice and the Espionage Statutes. The identification of those charges, and Trump’s comments in response to the search, would appear to indicate that the former-President mishandled classified information. Search warrants are based upon probable cause, however, the lowest evidentiary burden in criminal law. It is a long way from a search warrant to a conviction, which is based on proof beyond a reasonable doubt. Who knows whether the government, and, ultimately, a jury will get there.

There is another aspect of search warrant affidavits that needs to be addressed. These affidavits are based upon hearsay and other inadmissible evidence. The summaries of witness statements used by the FBI (and all other law enforcement agencies) can be skewed in one direction or another, and I have had cases where the summary of witness statements has been incomplete or simply wrong. Agents may be biased, confused, or mistaken, but the point is, a search warrant affidavit or an affidavit of probable cause supporting an arrest should never be accepted as fact. In my experience, there are mistakes in almost every affidavit filed by law enforcement officers, although, most times, the mistakes are not material.

Although it should be obvious, search warrant affidavits only present one side of the story, much like grand jury testimony. There is no defense attorney there to argue the other side or point out weaknesses in the document. It is possible that the execution of the search warrant is the beginning of a process that will ultimately lead to the former President’s prosecution, conviction, and incarceration. It is equally possible that nothing will come of the search warrant. We will simply have to wait and see where the facts lead.

Allen Weisselberg’s Decision to Plead Guilty and Cooperate

Perhaps the most imminent threat to Trump and the Trump Organization comes from Allen Weisselberg’s decision to plead guilty and cooperate against the Trump Organization in an upcoming trial. Whenever a codefendant agrees to cooperate with the prosecution, it is a serious problem. In this case, Weisselberg and the Trump Organization are accused of Income Tax Evasion. Specifically, Weisselberg has agreed to plead guilty to receiving $1.7 million in perks for which he did not pay taxes. As the former CFO of the Trump Organization, his cooperation virtually ensured the conviction of the Trump Organization.

The question, however, is what does this mean for Donald Trump and the Trump Organization? Was Donald Trump aware of the scheme? These are the issues the Manhattan District Attorney will have to investigate. It is also significant to note that these charges involve the evasion of state income tax. The same actions that constitute evasion of state income tax, however, would also most likely constitute evasion of federal income tax, a much more serious offense. If there is a federal criminal IRS investigation, we are not yet aware of it. However, it would seem unlikely that Weisselberg would have accurately completed his federal tax return when the state tax return was falsified.

Also, it is possible that the entire scheme was Weisselberg’s idea and that neither Donald Trump, nor anyone else in his family, knew what Weisselberg was doing. Trump, however, had previously referred to Weisselberg as a “great man” and the case against him as a “witch hunt”. Obviously, Trump was wrong. Weisselberg has admitted to being a felon and that the “witch hunt” actually was an investigation into legitimate crimes. It will be interesting to see if Trump can now reverse course and designate Weisselberg. He previously did so with Michael Cohen.

There will undoubtedly be further developments in the coming weeks and months. It will be interesting to see how these cases develop.

Dennis Boyle
Founder / Partner

Mr. Dennis Boyle is an accomplished white-collar criminal defense and complex civil litigation attorney who practices throughout the United States and internationally.

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