Political News

A look back at Trump's history of high-profile legal wranglings

Posted January 19, 2020 8:13 a.m. EST

— Donald Trump's divorce from his first wife Ivana had already devolved into a tabloid spectacle when, frustrated by the proceedings, the future President's temper flared.

"You're full of s***!" he exclaimed to the judge in her chambers when she suggested terms he deemed overly favorable to his soon-to-be ex-wife, accrding to Trump's lawyer at the time, Jay Goldberg.

As far as legal strategies go, it was unorthodox. Three decades later and facing another courtroom extravaganza, there are few indications the now-President's approach has changed.

For a man who has spent decades mired in various legal skirmishes, Trump's looming Senate impeachment trial -- one he's loudly declared "bulls***" -- represents the most closely watched of thousands of courtroom entanglements, even more so than the circus-like divorce from his first wife.

"That was one that caused me to say, 'holy crap, this is somebody that can't be messed with,'" Goldberg recalled this week of the outburst in the judge's chambers. "He never took things laying or lying down."

Before he took office, USA Today found Trump was involved in at least 3,500 legal filings in federal and state courts -- an unprecedented level of legal entanglements for a presidential candidate. That's on top of two high-profile divorces, various defamation suits and allegations of sexual harassment or assault, which Trump has denied.

"Trump saw law not as a system of rules to be obeyed and ethical ideals to be respected but as a potent weapon to be used against his adversaries or a hurdle to be sidestepped when it got in his way," writes James D. Zirin in "Plaintiff in Chief," an examination of Trump's long legal history. "His life in court took on an entertainment quality smacking of reality TV."

It's a tactic Trump honed early with the help of his lawyer Roy Cohn, the high-living and fearsome attorney who once helped Sen. Joseph McCarthy go after suspected Communists and led the prosecution of Julius and Ethel Rosenberg, which ended in the electric chair.

Life lessons

The two developed a friendship that went well beyond mere client-attorney ties.

Cohn, who died in 1986, helped introduce Trump into Manhattan society circles. He instilled in Trump an appreciation for brash legal dramatics and a set of tactics he's relied on ever since, in both his legal and political lives:

Flip the script: When Trump is accused of wrongdoing -- as he was during a 1973 housing discrimination case -- he usually goes after the accusers. During the housing episode, Trump tried to countersue the Justice Department for making false statements, but the allegations were dismissed. It's not unlike his near-constant accusations against Democrats of staging an impeachment "witch hunt" without due process.

Take it public: When the legal outlook seems dire, Trump often seeks to sway public opinion. He famously phoned in details of his personal life to New York City tabloids during his divorces, sometimes posing as a publicist. Now, Trump uses Oval Office photo-ops and campaign rallies to rail against the impeachment process.

After decades of hiring, firing, ignoring, scolding, regretting, suing and generally relying upon a wide network of lawyers, Trump is back on familiar terrain: devising a strategy that will lead both to his own acquittal and to the vanquishing of his opponents.

"He's not a person to be trifled with, but he will listen to the lawyers because he recognizes that they call the shots," said Goldberg, who like Cohn, is a lawyer to which Trump is constantly comparing his current attorneys, mostly unfavorably.

One former official interviewed during the Mueller investigation, onetime staff secretary Rob Porter, told the special counsel's office that Trump said "one of his biggest failings as President was that he had not surrounded himself with good attorneys," according to the FBI's account of the interview.

Near-perpetual legal proceedings

Ever since he made his first forays into real estate development, Trump has found himself embroiled in near-perpetual legal proceedings related both to his business and personal life. With them have come a constellation of attorneys -- not all of whom Trump has found satisfactory.

"I don't like lawyers," he wrote in "The Art of the Deal," his 1987 book. "I think all they do is delay deals, instead of making deals, and every answer they give you is no, and they are always looking to settle instead of fight."

Trump has taken a similar view in the Oval Office. When he was preparing to fire FBI Director James Comey, he preempted expected pushback from his team of lawyers by declaring, "Don't talk me out of this. I've made my decision."

Later, when one of those lawyers began taking notes of their conversations, Trump snapped.

"Why do you take notes? Lawyers don't take notes. I never had a lawyer who took notes," he told onetime White House counsel Don McGahn, according to the Mueller report. "I've had a lot of great lawyers, like Roy Cohn. He did not take notes."

Trump has warmed more toward lawyers who avoid advising him against things, or aren't offended when he ignores their advice.

One, Michael Cohen, served as Trump's close aide and fixer for years before making a dramatic break, implicating the President in campaign finance violations before himself going to prison.

Another of Trump's attorneys, Rudy Giuliani, has expanded the role of a personal lawyer. His adventures in Ukraine, designed to surface damaging material on former Vice President Joe Biden, were partly what led to the current impeachment saga.

In some ways, Trump's long-held view of the courtroom (like the boardroom and briefing room) as a theatrical venue above all squares well with a nationally televised impeachment trial. Trump's lawyers and allies hope to capture public sentiment by accusing Democrats of unfairly targeting him after losing the last election.

The current players

Many of Trump's closest advisers have warned him against turning the trial into a circus, believing a more staid affair will better convince Americans the expected acquittal is legitimate.

"He'll be respectful of the process. It will shock you," Goldberg predicted. "After he's acquitted, then he'll open up on the Democrats."

"This case will proceed in a very orderly way without showmanship because the President's lawyer -- Pat -- is a conservative lawyer, erudite, and he will call the shots," he said.

Pat is Pat Cipollone, the articulate and buttoned-up current White House counsel who is expected to lead the President's legal team alongside Jay Sekulow, who has served as a personal attorney for Trump.

On Friday, the legal team announced several additions: former independent counsel Kenneth Starr, whose investigations into Bill Clinton led to the country's last impeachment trial; Robert Ray, who succeeded Starr as independent counsel; defense attorney Alan Dershowitz, whose renown extends back to his days defending O.J. Simpson; Pam Bondi, the former Florida attorney general; and Jane Raskin, a white-collar defense attorney who worked for Trump during the Mueller investigation.

As he has for much of his life, Trump again finds himself surrounded by lawyers. It's not unlike the scene that played out in his Manhattan office 30 years ago as he sought an attorney to represent him in his first tabloid-bait divorce. A swarm of attorneys descended, hoping to proffer their services upon the real estate mogul.

"My office resembled an emergency room, but instead of patients, there were lawyers crowding around," Trump wrote in one of his books, "The Art of the Comeback."

The lawyers, who Trump claimed were meting out their services free of charge, each offered their own take on a legal strategy.

"No one satisfied me," Trump wrote.

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