In his many business failures, (six bankruptcies plus an additional twelve failed businesses) he threatened his adversaries with personal attacks and the prospect of endless and expensive lawsuits. So contactors and workers routinely got cheated out of everything or settled for fractions of what they were due.
In his book Plaintiff in Chief: A Portrait of Donald Trump in 3,500 Lawsuits, former federal prosecutor and "middle-of-the-road Republican" James D. Zirin describes Donald Trump's vicious, punitive, and often groundless lawsuits: "He sued as a means of destroying or silencing those who crossed him." In an April 2020 interview by Robin Lindley on the American Bar Association website, Zirin said Trump followed the tactics of his hero, mentor, and lawyer, the notorious (and ultimately disbarred) Roy Cohn, to whom he spoke as many as six times a day: "If you're charged with anything, counterattack...try to undermine your adversary...work the press...It doesn't matter how tall a tale it is, but repeat it again and again... settle the case, claim victory and go home."
And that's exactly what Trump has always done. Before his cases go to trial he settles with sealed non-disclosure agreements. Zirin reports that in one case with a journalist, Trump lied 32 times in the deposition but then settled before the case went to trial--his usual strategy, according to Zarin. Trump knows that if cases go to trial he will lose.
Earlier this year, Trump filed defamation suits against the New York Times and the Washington Post for articles alleging he invited Russia to help him win the 2016 election. After gaining political benefit from these lawsuits in playing tough guy for his base and imposing punishing legal costs on the Times and Post will he dare take these cases to trial or will he drop them if they are not thrown out by judges? Will he allow his possible Russian connections and the "sham" Mueller investigation to be thoroughly examined in a courtroom? Do we really need to debate the answer to these questions? Keep in mind also that Trump plays these pricey legal games at no financial cost to him since his legal fees are paid by donors.
The Roy Cohn game plan of bleed them financially then slam them personally often worked for Trump. That's why many of the 25 women who have accused him of sexual assault or misconduct gave up in terror of his shameless smears that would drag them down to the gutter. That's where he operated from--his situation room.
The truth is that in almost all these instances he was bluffing. And it worked and continues to work--except when it doesn't work. When opponents called his bluff and said "I'm not backing off" Trump settled with substantial payoffs and hush money like the $130,000 he paid to silence Stormy Daniels.
When threats and smears fail, Donald Trump will cave and settle because he will never willingly step into a courtroom for a trial. He knows that in a trial he can be cross-examined, putting him in danger of committing perjury. Also, his adversaries can request records in the process of discovery-- financial and other documents that he desperately fights to conceal. And his guilt in most cases would be so transparent that he would lose and get slammed by judges. When he was forced into court by prosecutors in the fraud case against Trump University, he had to settle for a whopping $25 million. Zirin describes an earlier case with a union representing immigrant Polish workers. Trump had to settle for 100 cents on the dollar after the trial judge said that his testimony was completely lacking in credibility.
So his bluffs end at the point of standing up to him with the words: "Let's go to trial."
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