By Haddon Libby

The latest criminal charges against former President Donald Trump are a continuation of his lifetime of behavior that regularly lands him in court.  Over his fifty-year career, Trump has amassed more than 4,000 lawsuits – some as plaintiff and as defendant.  That equates to eighty lawsuits a year or one every four to five days…for fifty years!

Let’s review some of the court cases and serious investigations where our Plaintiff-in-Chief is currently Defendant-In-Chief. While everyone is innocent until being proven guilty, where you find thousands of smoke clouds, there must be more than a few hundred fires – particularly when you consider that the pyromaniac has admitted to starting many of them.

  • Taking top secret documents from the White House and failing to relinquish control when asked for the return of those documents.  This 37-count indictment comes solely from his behavior and efforts not to comply with the law.
  • Fraudulent business practices.  Trump structured hush money (aka extortion) payments to porn star, Stormy Daniels and two others in the final days of the 2016 Presidential election.  Trump had supposedly been playing bridge or something with Stormy while Melania was pregnant with Baron.  As a reminder, Trump has faced numerous sexual misconduct cases between 1970 and 2005 including one with Jeffrey Epstein, a close friend of his in the late 80s and early 90s.
  • Fraudulently overstating the values of properties to defraud banks to get larger loans under better terms.  The same behavior has been used to overstate donations and avoid taxation.
  • Class action lawsuit related to ACN, a multi-level marketing company that paid the President and his family endorsements while in elected office.  The fraud is that the family never disclosed that they were paid spokespeople of the company.   An additional problem is that none of this was disclosed while serving as President.
  • Tenants of rent-controlled properties owned by the Trump family since The Donald was a child are suing for fraud and racketeering.  This lawsuit stems from the alleged behavior of overcharging for appliances to offset the limits of rent control laws.  The Trump family has a history of issues with low-income rental properties in New York City dating back to 1973.
  • Numerous lawsuits related to the events of January 6, 2020.
  • Numerous lawsuits and investigations into efforts to overturn the 2020 election.
  • While not yet in the courts, the Justice Department is looking into stock trades and other communications that took place in the Special Purpose vehicle (SPAC) that was meant to launch Truth Social as a rival to Twitter.

We should not forget recent lawsuits that are now settled:

  • Trump Organization found guilty of tax fraud landing the long-time CFO in jail.  Additoinal charges now face member of the Trump family.
  • Trump Inaugural Committee siphoned donations for the inauguration into Trump family accounts.  This lawsuit was settled for $750,000 in May 2022 by the Trump Organization.

Let us not forget Trump University where numerous lawsuits were settled for $25 million.  Prior to settling, Trump use of his signature move- counter-suing the plaintiff and using the cost of litigation against them.  While it is a very effective technique, the better way to handle all of this is to avoid the behaviors that continually result in the use of the court systems.

The United States has many problems.  Having someone of such questionable character in charge should make all of us shudder.  There are few people ever to weaponize the court systems like Trump.  As we enter a new election cycle, people need to ask themselves if there are better options available than his man.  It probably is not President Biden but one of the other contenders.  Surely, we can do better as a country than electing a man of Trump’s character to the highest office in the land.

Haddon Libby is the Founder and Chief Investment Officer of Winslow Drake Investment Management.  For more information on our services, please visit.