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‘Teflon Don?’: The Legal Troubles Of Donald Trump

As his successful run for president indicated, little seems to stick to Donald Trump. Failed business ventures, sexual assault allegations, even impeachment have come and gone and ‘The Donald’ lives on. That said, the tides could be turning. Trump is returning to life as a private citizen in a world perhaps more polarised than ever and less favourably disposed to him because of his actions. Now, lawsuits are piling up against him. The question which remains then is whether Trump’s Houdini act can continue or will he be held accountable for his supposed crimes?


Trump is no stranger to legal problems. Indeed, before he became president, he had been involved in multiple lawsuits. In 2016, USA Today revealed that then-candidate Trump had been embroiled in at least 3,500 lawsuits. In 1,450 of these lawsuits, Trump was the defendant and 150 concerned bankruptcy, a third party or another issue. In the 1,350 cases where the record establishes an outcome, Trump won just 450 cases. The numbers are astronomical. As many observed, it was unprecedented for a candidate for the highest office in the land to have been involved in so much legal dispute.


What is less expected is the range of issues. Trump has been accused of destruction of records and deleting emails, tax avoidance and has also suffered six corporate bankruptcies. Deleting emails also came up in multiple cases as Trump has been accused of overseeing the deletion of company records, refusing to comply with prosecutors’ requests for documents, and wiping email servers. In this respect, Trump was obstructing justice, a charge that would become synonymous with his presidency.


Yet, the legal issues were not limited to Trump’s business dealings. In October 2016, a matter of weeks before the election, an Access Hollywood tape was leaked to the Washington Post. In this, Trump detailed his sexually aggressive behaviour, coupled with disparaging comments towards women. This culminated with the now infamous line “Grab them by the pussy”.


Although this revelation had a negligible effect on his electoral prospects, it brought to light charges against Trump concerning his behaviour towards women. In total 26 incidents of “unwanted sexual contact” and 43 instances of inappropriate behaviour involved the president, all of which were collected in the book All the President’s Women: Donald Trump and the Making of a Predator.


One of the earliest allegations came from Trump’s first wife, Ivana Trump. Taken from a sworn deposition which was then recorded in a 1993 book, Ivana used the word ‘rape' to describe a sexual encounter with Trump. She has since softened her wording, saying that she did not use the word in the literal sense. The Trump defence, however, is jarring for the reason that they claimed one cannot rape a spouse. The exact phrasing was “you can't rape your spouse” came from the now-disgraced attorney for Trump, Michael Cohen. Later, Cohen backtracked from these comments, describing them as “inarticulate”.


This all came to light when Trump was still just a candidate in a packed Republican field in 2015. Cohen issued this statement and the backlash was against him. It was said that Trump did not know of his lawyer’s comments and disagreed with them, which followed his team’s statement that “This is an event that has been widely reported on in the past, it is old news and it never happened”. This comment presaged what became part of the Trump playbook when dealing with a scandal: deny, discredit, deflect and then distract. The mastery displayed at weathering legal storms explains why so little would stick to Trump. He would send his infantry of loyalists out to take the initial heat before returning to the public eye, bashing the charge and playing the victim.


These are not legal challenges in the express sense of being charged and subsequently being a participant in a trial. However, when the word rape is used, legal associations are drawn. Although Ivana may have not used the word ‘rape’ literally, Jill Harth described her interaction with Trump as “attempted rape”. In 1993 at his Mar-a-Lago resort, Harth alleged that Trump pushed her into one of the children’s bedroom and groped her. This spiralled into a 1997 lawsuit, but nothing came of it except a confidential settlement which also led to Harth withdrawing her suit. It only returned to the news cycle in 2016. When Trump was asked about it, he dismissed it as “meritless”. Harth was also pressured to retract all that she had said in a New York Times piece by the Trump campaign


Now, with presidential immunity no longer a privilege enjoyed by Trump, the lawsuits are again piling up. Perhaps most worrying for Trump is Manhattan District Attorney, Cyrus Vance Jr, who is pursuing a criminal investigation into Mr Trump and The Trump Organization.


Beginning in 2018 with Trump’s former attorney Michael Cohen and the hush money payment to Stormy Daniels, Vance is investigating the more than $250 million in loans Trump took out on some of his best-known Manhattan properties. The scope of Vance’s investigation is broader, exploring possible banking, tax and insurance-related fraud committed by The Trump Organisation. There is currently no timeline for when charges might be brought against Trump and the Trump Organisation. Vance has already subpoenaed Trump’s tax returns in a protracted legal battle. This victory was reaffirmed when the Supreme Court refused to halt the turnover of his tax returns.


Also in New York is the investigation by New York Attorney General Letitia James into possible real-estate fraud. This began as a civil case, meaning that, if any wrongdoing was found, James could only sue Trump or his businesses. Yet, James announced in May 2021 that her investigation was now no longer purely a civil inquiry but also a criminal probe. This translates to James looking for intent to do wrong rather than just doing wrong. The full scope of James’s enquiry remains unknown, with no charges filed as of yet. Nevertheless, the recent development in James’s investigation has the potential to morph into a real threat to Trump and those in his orbit.


Now, with these latest legal challenges, it is simply a question of time. Eventually, there will be some form of resolution. Ultimately, however, any legal verdict will be as divisive as Trump’s presidency. For Trump’s critics, only a conviction will suffice and make up for the damage done by his presidency. For his fans, of which there are still many, an acquittal would vindicate the numerous witch-hunt claims made.


Written by James Hingley


James Hingley is a columnist at DecipherGrey.


Photograph: Gage Skidmore|Flickr.com