Fifty years ago, Donald Trump learned the legal strategy that would repeatedly get him out of tight legal jams.

It was 1973 and the Justice Department had just filed a civil rights lawsuit against Trump and his father Fred Trump. The complaint alleged that the Trumps and their company, which managed some 14,000 apartments in Queens, Brooklyn and Staten Island, had violated the Fair Housing Act by systematically flagging the applications of Black renters and steering them away from available units.

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. The Trumps settled the case two years later, agreeing to a consent decree that included giving a weekly list of vacancies to the New York Urban League. 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. Warren Harding was investigated by his own vice president and successor, Calvin Coolidge. Nixon would have been the target of investigations for years if Gerald Ford had not pardoned him in September 1974, a month after Nixon resigned from 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.”

In Georgia, Fulton County District Attorney Fani Willis is looking into how Trump pressured election officials to swing the 2020 presidential election in his direction. The House Jan. 6 Committee and the Department of Justice are both looking at what role Trump played in the lead up to the deadly attack on the Capitol Building to stop the lawful counting 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.

In all of the ongoing cases, Trump is employing the tried-and-true playbook he first learned all those years ago from Cohn for staying out of prison and staying in business, according to Jennifer Taub, a professor at Western New England University School of Law who has tracked the ways that Trump had evaded accountability for decades.

Roy Cohn (L) and Donald Trump attend the Trump Tower opening in October 1983 at The Trump Tower in New York City.<span class="copyright">Sonia Moskowitz—Getty Images</span>
Roy Cohn (L) and Donald Trump attend the Trump Tower opening in 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.”

But Trump has found himself in legal hot water before and managed to dodge serious ramifications. 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 here was continuing a long-established pattern of responding to accusations with a denial, even when he was aware that evidence would most likely later emerge proving him 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 has refused to back away from this denial even after his supporters violently attacked the Capitol and, now, candidates who openly refute the legitimate results of the 2020 elections are running for office in states that could determine the outcome of the next presidential race.

Deflect to 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.<span class="copyright">Tom E. Puskar—AP</span>
Former President Donald Trump takes the stage at a campaign rally in Youngstown, Ohio. on Saturday, Sept. 17, 2022.Tom E. Puskar—AP

Last month, four days after the Mar-a-Lago search, Trump compared his predicament, where he kept hundreds of government documents in unsecured personal boxes, to the orderly and conventional process by which former President Barack Obama set up his presidential library. Obama has worked with the National Archives to properly secure the presidential records and make them available for his library in Chicago.

But Trump used that allegation as a distraction. “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.

His legal filings in the Mar-a-Lago case also reflect how Trump is using his unique situation as a former president with ambitions to seek another term to divert attention away from his actions, by suggesting those investigating him are doing so 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 has also tried to deflect focus from his actions by raising the specter of political violence if he is charged in the Mar-a-Lago case, a tactic he used in the buildup and aftermath of the deadly attack on the 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.”

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.

As a presidential candidate in 2016, Trump broke decades of precedent when he refused to make his tax returns public. 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. Efforts by Democrats in Congress to see them have been stymied in court. 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. In 1988, Trump agreed to pay a $750,000 penalty to settle a suit with the U.S. Federal Trade Commission for violating antitrust laws over stock trades he 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. His $25 million settlement in the Trump University suit followed six years of litigation.

Don’t Put Anything in Writing

There’s little record of Trump owning a personal computer or writing emails. When running his business, his staff have described that he rarely put anything in writing or gave direct orders. 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 has said repeatedly that the papers at Mar-a-Lago were declassified. Now it is up to Trump to show that 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 berated his White House counsel Don McGahn for taking notes during an Oval Office meeting about the Mueller investigation. “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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