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How Trump Survived Decades of Legal Trouble

FDonald Trump was born fifty years ago and learned the law strategy that would get him out from tight legal situations.

The Justice Department was just about to file a civil rights suit against Trump’s father Fred Trump in 1973. It was alleged that Trumps and his company managed over 14,000 apartments in Queens Brooklyn, Staten Island and Brooklyn. The Fair Housing Act had been violated by the Trumps.

To push back, the Trumps hired the famously combative Roy Cohn—Senator Joseph McCarthy’s chief counsel during the 1950s Red Scare hearings—and sued the Justice Department for $100 million, claiming defamation. Trumps agreed to settle the matter two years later. This included a weekly update of the New York Urban League’s vacancies. Trump later boasted that he ended up “making a minor settlement without admitting guilt.”

That early entanglement with the Justice Department drove home to Trump key lessons he’s carried with him through five decades of lawsuits and tax challenges, two impeachments and now, more legal investigations than any other former President has ever faced.

On Wednesday, New York Attorney General Letitia James compounded Trump’s legal woes, announcing that the state was suing Trump, his three adult children, the Trump Organization, and senior management in the company, alleging business fraud involving the value of assets to banks, insurance companies and the state tax authorities.

The sheer number of investigations and the increasingly tangled defenses his legal team is having to put on paper and argue in court amount to a stress test of Trump’s standard strategy to deny, deflect, delay, and not put anything in writing.

“I don’t think there’s any other president who was in a similar legal jeopardy” after leaving office, says Timothy Naftali, a historian at New York University and former director of the federal Richard Nixon Presidential Library and Museum. Calvin Coolidge, his vice-president and successor to Nixon, investigated Warren Harding. Nixon would still be under investigation if Gerald Ford hadn’t pardoned him on September 24, 1974, just a month after Nixon quit office.

“Even Nixon pales by comparison,” says Norman Eisen, an anti-corruption expert at Brookings Institution and the former special counsel to the Democrat’s House Judiciary Committee from 2019 to 2020 during Trump’s first impeachment. “Nixon just had one Watergate scandal. Trump has had a succession of them, each one more concerning than the last.”

Fulton County District attorney Fani Willis in Georgia is investigating Trump’s pressure on election officials to vote for him. Both the House Jan. 6 Committee as well the Department of Justice are investigating Trump’s involvement in the events that led to the terrorist attack on Capitol Building, which was meant to prevent the lawful count of electoral college votes. Federal prosecutors have an active criminal investigation into how and why Trump took thousands of government documents—many containing state secrets—to his residence at Mar-a-Lago and why he refused repeated requests to return them.

And New York’s civil lawsuit announced by James on Wednesday is on top of a separate criminal investigation out of the Manhattan District Attorneys’ Office into the Trump Organization that is set to go to trial in October.

Learn More: Donald Trump: The Main Ongoing Investigations

Trump has continued to follow the proven strategy that Cohn taught him years ago. This is the best way for Trump to stay out of jail and keep his business afloat, according Jennifer Taub of Western New England University School of Law. Taub was a Western New England University School of Law Professor who had been tracking Trump’s actions for many decades.


Roy Cohn (L), and Donald Trump attended the opening of Trump Tower, October 1983 at The Trump Tower in New York City.

Sonia Moskowitz—Getty Images

“Here’s what he learned from Roy Cohn: Don’t put things in writing, punch back harder, focus on optics, who cares what the courts say,” says Taub, who is the author of the book, Big Dirty Money: The Shocking Injustice and Unseen Cost of White Collar Crime.

Those methods have been perhaps most apparent in Trump’s actions in the wake of the Mar-a-Lago search by the FBI, and are likely to emerge again as he defends himself against the latest lawsuit from New York into his business practices, which Trump has called a “politically motivated Witch Hunt.”

Trump was in serious legal trouble before, but he managed to avoid major consequences. Here’s a look at the four key strategies Trump has turned to before to elude legal trouble.

Deny, Deny, Deny

The day that FBI agents searched Mar-a-Lago and found dozens of documents with classified markings on them mixed in with Trump’s personal effects, Trump denied he had blocked multiple requests for him to return the records for months. “After working and cooperating with the relevant Government agencies, this unannounced raid on my home was not necessary or appropriate,” Trump said in a statement on Aug. 8. Four days later, on Aug. 12, Trump wrote on his social media account, “They could have had it anytime they wanted—and that includes LONG ago. ALL THEY HAD TO DO WAS ASK.”

The National Archives soon showed that officials had had more than a year of exchanges with Trump’s lawyers about returning government documents held in Florida.

Trump continued a tradition of responding to allegations with denials, even though it was clear that evidence would eventually emerge showing him as a liar.

In one striking example from his presidency, after notes were made public from a 2019 phone call in which Trump urged Ukraine’s new President, Vladimir Zelensky, to launch an investigation into Joe Biden, Trump denied he had done anything wrong in using the power of the U.S. presidency to pressure a foreign country to investigate one of his political rivals. Trump called it a “perfect call.”

And famously, Trump denied ever asking Russia to help him win the 2016 election, and called the investigation into Russia’s efforts to influence the outcome of the election a hoax and a witch hunt. He has made those denials for years, even after a campaign event in July 2016 when he publicly encouraged Russian hackers to find and leak his opponent Hillary Clinton’s emails, saying, “Russia, if you’re listening, I hope you’re able to find the 30,000 emails that are missing.”

One of Trump’s most far reaching denials is still rattling the foundations of U.S. democracy. On Nov. 7, 2020, when Joe Biden’s tally in the presidential election reached an insurmountable lead, Trump wrote on Twitter, “I WON THIS ELECTION. BY A LOT!” He has stuck to that lie for nearly two years. Trump did not back down from his denial, even when his supporters assaulted the Capitol. Candidates who have openly denied the legitimacy of 2020 election results are now running in states that will determine next year’s presidential race.

You can also deflect other shiny objects

When cornered, Trump’s approach is to deflect, attack others, and distract from what he’s accused of doing, a strategy that often goes hand in hand with his denials.

In the 1970s, when Trump was under investigation for housing discrimination, his lawyer Roy Cohn accused the Department of Justice of using “Gestapo” tactics and called investigators “storm troopers.”

In 2016, during Trump’s first presidential campaign, Trump criticized the federal judge handling a lawsuit against his business Trump University, saying Judge Gonzalo P. Curiel was “totally biased” and “unfair.” Trump was campaigning at the time on a promise to build a wall on the border with Mexico, and during an appearance on CNN, Trump said Curiel should recuse himself, arguing “this judge is of Mexican heritage, I’m building a wall.” Trump ended up agreeing to a $25 million settlement in the case.

Former President Donald Trump takes the stage at a campaign rally in Youngstown, Ohio. on Saturday, Sept. 17, 2022. (Tom E. Puskar—AP)

A campaign rally was held in Youngstown (Ohio) by former President Donald Trump. September 17, 2022.

Tom E. Puskar—AP

Trump, who had kept hundreds of government documents and other personal papers in his Mar-a-Lago home, compared it to the conventional, orderly process that former President Barack Obama used to set up his presidential library. Obama has cooperated with National Archives in order to protect the Presidential records and make them accessible for his Chicago library.

Trump used this allegation to distract. “The bigger problem is, what are they going to do with the 33 million pages of documents, many of which are classified, that President Obama took to Chicago?” Trump wrote on Aug. 12.

Trump also used his Mar-a-Lago situation to show that he was a former president who wants to be a politician. He suggested that those who are investigating him were doing it for political reasons. “President Donald J. Trump is the clear frontrunner in the 2024 Republican Presidential Primary and in the 2024 General Election, should he decide to run,” reads the Aug. 31 court filing from Trump’s lawyers requesting a special master review the documents seized from Mar-a-Lago. “Law enforcement is a shield that protects Americans. It cannot be used as a weapon for political purposes.”

Trump tried to distract attention from his actions, raising the possibility of violence political if he was charged in Mar-a-Lago. This tactic was used by Trump in the aftermath and buildup of the attack on Capitol. Speaking on Hugh Hewitt’s radio show on Sept. 15, Trump said if he were charged, “I think you’d have problems in this country the likes of which perhaps we’ve never seen before.”

Delay. Delay. Delay

Trump’s request that a federal judge in Florida name a “special master” to review the documents seized from Mar-a-Lago takes another page from Trump’s playbook: delay the process as much as possible.

Judge Aileen Cannon has stalled the Department of Justice’s investigation while another federal judge, Raymond Dearie, reviews what was taken to sift out anything that might be considered protected attorney-client privilege or that Trump could claim shouldn’t be handed over because it is part of internal deliberations while President. In a court filing on Sept. 19, Trump’s legal team asked Dearie to extend the timeline of his review, writing, “we respectfully suggest that all of the deadlines can be extended.”

Learn more: Special Master Appears Skeptical of Trump’s Claims He Declassified Mar-a-Lago Documents

Delaying procedures and investigations has been a common technique of Trump’s, says Taub, the expert on white collar crimes. “If you can just get someone on your side. If you can just delay, you live another day,” Taub says.

Trump, as a 2016 presidential candidate, broke many decades of tradition by refusing to release his tax returns. He continued to put off releasing his returns for two election cycles, insisting he couldn’t because his taxes were under audit by the Internal Revenue Service. Democrats have failed to obtain the tax records, despite their efforts. House Democrats first sued to get Trump’s tax records in 2019, saying the records would allow Congress to assess if Trump had taken “inappropriate advantage” of the tax laws.

Trump’s delay tactics often eventually conclude with settlements. Trump paid $750,000 to resolve a lawsuit with the U.S. Federal Trade Commission in 1988 for violating antitrust laws regarding stock trades he had made in 1986. In 2015, the Treasury Department’s Financial Crimes Enforcement Network imposed a $10 million civil penalty on the Trump Taj Mahal Casino Resort for violating the Bank Secrecy Act from 2010 to 2012. Six years of litigation led to his $25 million settlement in Trump University’s suit.

Don’t Put Anything in Writing

There’s little record of Trump owning a personal computer or writing emails. His staff described Trump’s inability to write anything or give direct orders when he was running his business. Trump’s former in-house lawyer Michael Cohen told Congress in 2019 that Trump spoke to him in “code” when he was giving him instructions about how to lie to Congress and Special Counsel Robert Mueller about Trump projects in Russia.

Being president meant more of Trump’s actions and directives were recorded, even when he didn’t want them to be. Trump’s July 2019 phone call with Zelensky, for example, was documented by notetakers in the White House Situation Room, who routinely document conversations between Presidents and world leaders. Even though Trump denied there was anything wrong in the call, the notes describe Trump telling Zelensky, “There’s a lot of talk about Biden’s son, that Biden stopped the prosecution and a lot of people want to find out about that so whatever you can do with the Attorney General would be great.”

Now that Trump is back in court and trying to defend his decision to keep government documents at Mar-a-Lago, what he’s written down and what he hasn’t comes with higher legal stakes. The FBI’s list of papers seized from Mar-a-Lago listed documents with Trump’s handwritten notes on them. Trump claims that Mar-a-Lago’s papers have been declassified. Trump must now prove this in court. If there’s no record of Trump declassifying those documents, his defense could be more challenging. Suddenly, Trump’s habit of avoiding putting things in writing could be a liability.

Trump once criticised Don McGahn as White House counsel, for taking notes in an Oval Office meeting regarding the Mueller probe. “Why do you take notes? Lawyers don’t take notes. I never had a lawyer who took notes,” Trump said. McGahn said he took notes because he’s a “real lawyer” and it creates a record. “I’ve had a lot of great lawyers, like Roy Cohn. He did not take notes,” Trump said.

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