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  • Writer's pictureThe San Juan Daily Star

Donald Trump’s time-tested legal strategy: Attack and delay


Former President Donald Trump speaks during a campaign rally at Waco Regional Airport, in Waco, Texas on March 25, 2023.

By William K. Rashbaum, Maggie Haberman, Charlie Savage and Jonah E. Bromwich


Attack. Attack. Attack.

Delay. Delay. Delay.


Those two tactics have been at the center of Donald Trump’s favored strategy in court cases for much of his adult life and will likely be the former president’s approach to fighting the criminal charges now leveled against him if he sticks to his well-worn legal playbook. In fact, his attacks against both the prosecutor and the judge in the case have already begun.


Over more than four decades, Trump has sued and been sued in civil court again and again. In recent years, he has faced federal criminal investigations, congressional inquiries and two impeachments. He has neither a law degree nor formal legal training, but over the course of that long history, he has become notorious in legal circles for thinking he knows better than the lawyers he hires — and then, very often, fires — and frequently is slow to pay if he does at all.


The former president now faces an indictment stemming from a hush-money payment made to a porn actress in the final days of the 2016 presidential campaign. Trump, who has steadfastly contended he committed no crime and almost certainly will decline any plea deal, will fight the case in state Supreme Court in Manhattan, New York. The battle there will play out in front of the same judge who last year presided over the tax fraud trial of Trump’s family real estate company — a trial that ended in a conviction on 17 felonies.


The details of Trump’s defense strategy are still unclear because the specific charges in the indictment against him will stay under seal until his arraignment Tuesday.


But two things seem certain: The defense approach will include aggressively attacking the credibility of Michael Cohen, Trump’s onetime fixer and lawyer who is expected to be the prosecution’s central witness; and, if the indictment relies on a legal theory that has never been evaluated by a judge, the defense will also zero in and zealously challenge it.


Cohen, who broke with Trump in 2018 and testified before the grand jury that indicted him, is expected to tell a trial jury that the former president directed him to pay off the porn actress, Stormy Daniels, and that Trump reimbursed him and helped to cover up the entire hush-money affair.


Cohen was federally prosecuted for the hush-money payment and pleaded guilty in 2018 to campaign finance violations and other crimes.


His guilty plea to those crimes, which include lying to Congress, and his years of public statements will make him a sure target on cross-examination for Trump’s lawyers, while prosecutors will be likely to counter that he lied on behalf of Trump and that his story has remained consistent for years.


The judge, Juan Merchan, who in more than 16 years on the bench has earned a reputation for being thoughtful and measured, keeps to a tight schedule in court and seeks to maintain a certain level of decorum there, despite the sometimes rough-and-tumble atmosphere in state criminal proceedings. He likely will have little patience for the former president’s attack-and-delay strategy.


Merchan did not have to wait long to see Trump’s tactics in full flower. On Friday morning, less than 24 hours after the former president had been indicted, he lashed out at the judge.


Trump wrote on his Truth Social website that Merchan had “railroaded” Allen Weisselberg, the former chief financial executive of the Trump Organization, who is serving the final weeks of a 100-day sentence in the Rikers Island jail complex in New York City after pleading guilty to tax fraud charges in the case against the former president’s company.


Referring to his upcoming arraignment before Merchan scheduled for Tuesday, he wrote, “The Judge ‘assigned’ to my Witch Hunt Case, a ‘Case’ that has NEVER BEEN CHARGED BEFORE, HATES ME.”


Asked about the sentiment the former president expressed in his post, one of his lawyers said Sunday morning that he had no problem with Merchan. “He has a very good reputation,” Joseph Tacopina said on CNN’s “State of the Union,” adding that “I have no reason to believe this judge is biased; I have not been before him on this matter.”


Trump also attacked Alvin Bragg, the Manhattan district attorney, in the hours after news of the indictment broke. “Why & who would do such a thing? Only a degenerate psychopath that truely hates the USA!” the former president wrote.


Trump’s intensely litigious nature has made his strategy more visible over the years than it might otherwise be. He has long used delay tactics in legal matters that emerged from business disputes, and since becoming a politician, he has repeatedly tried to throw sand in the gears of the legal system, using the resulting slow pace of litigation to run out the clock until seismic events shifted the playing field.


One of the more notable examples came in the early stages of the Manhattan district attorney’s investigation that led to the indictment Thursday. Prosecutors in 2019 subpoenaed Trump’s accountants for his tax returns and other records, and the president sued in federal court to block the document demand, a move that delayed the inquiry for 18 months while the case went to the Supreme Court of the United States — twice. (Trump lost both times.)


Christopher Kise, a lawyer who represents Trump in some of his cases, defended the former president’s often-used approach and argued that it is not significantly different from what takes place in many legal cases.


“He has adopted a strategy that is consistent with what any sophisticated defense lawyer would advise, and it works,” Kise said in an interview.


“And the reason it works is, it’s the right strategy,” he said, contending that “it’s not really delay for its own sake.”


He argued, however, that Trump’s approach may be different in the New York case.


“Transparency is his ally in this circumstance, because the more facts that become public, the more I think the public will be truly outraged by the level of injustice and manipulation that’s taking place in this case,” Kise said.


Timothy O’Brien, the senior executive editor at Bloomberg Opinion and a former reporter and editor at The New York Times, is somewhat familiar with Trump’s legal strategy. Trump unsuccessfully sued him for libel in 2006 over a book he wrote about the then-real estate developer, a case that dragged on for five years.


He said Trump learned from his first lawyer, Roy Cohn, a fixer who attacked the legal system while leveraging connections in an attempt to instill fear of financial or reputational damage in his opponents.


The former president, O’Brien said, relies “on everyone else to play by the rules while he bends or breaks them.”


But in previous legal entanglements during his presidency, the system itself repeatedly protected him because Justice Department policy barred indictment of a sitting president.


And then, when Trump was twice impeached by the House, his relationship with Mitch McConnell, the Senate Republican leader, meant he was never at risk of being convicted or removed from office during his first Senate trial.


During the second, focused on the attack on the Capitol by a pro-Trump mob on Jan. 6, 2021, Republicans were still mostly unwilling to vote to convict him.


But now the former president has no such armor protecting him as he faces the most significant threat he ever has.

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