Donald Trump, a billionaire in some danger of prosecution, has been doing a great deal of back-seat lawyering in recent weeks.
He’s not the first billionaire to believe that learning the law and acquiring decades of experience have little to do with mounting an effective defense. And he’s not the first to think he’s smarter than a prosecutor, in this case, Special Counsel Robert S. Mueller III, a former deputy attorney general who oversaw the prosecutions of Manuel Noriega and John Gotti before becoming director of the FBI.
Thirty years ago, Michael Milken — the head of the high-yield bond trading department at Drexel Burnham, but better known as the king of “junk bonds” — made the same mistake.
Milken wasn’t known for not paying his bills and daring creditors to sue him and offending women so blatantly that no quality law firm could take him on without howls of protest and mass defections from its female colleagues, so he was able to hire Edward Bennett Williams, one of the most respected lawyers in the country. Williams had persuaded prosecutors not to indict oil man Marvin Davis, led the Security and Exchange Commission to drop its case against conglomerateur Charles Bluhdorn, and successfully defended former CIA chief Richard Helms and Treasury Secretary John Connally. He looked forward to scoring another victory over the SEC and crushing U.S. Attorney Rudolph Giuliani, who he described as “raw political meat, a mediocre lawyer with all the drive to get to the top of a shitty place like New York.”
His biggest problem, he sensed, was his client.
Michael Milken knew the bond market, and in a granular way — that is, he knew who owned every bond and at what price. He worked like an animal, and when he needed to learn something he didn’t know, he could absorb massive data overnight. But his relentless optimism required him to resist or deflect personal insight. He failed to see that Ivan Boesky was a career criminal. And he couldn’t process the reality that the government saw him as one as well.
His first meeting in the Williams & Connolly conference room was revealing. As Williams and Milken’s other top-tier lawyer, Arthur Liman, took Milken through the case they anticipated the government to present, their client shuffled paper. He’d reach into a canvas bag, remove its memos and reports, sort them and place them in another canvas bag. Then he’d start again. Rarely did he make eye contact with anyone.
“For chrissakes, Michael, you’re driving me crazy!” Williams finally shouted. “Will you please pay attention?”
Milken looked down at the table. “I’m sorry, but I was listening.”
“I know you hear me,” Williams said. “Just let me know it, okay?”
Milken nodded, focused for almost an hour — and then resumed sifting the paper in his bags.
Williams concluded that Milken would be a terrible witness at trial. “Some guys can’t see the forest for the trees,” he told an associate. “This guy can’t see beyond the moss on the bark.”
Milken’s pathological insularity worked for him in business; it looked like hyper-focus. But his business success had been so meteoric that only his brother Lowell dared to disagree with him. Tellingly, Lowell listened to his lawyers, and they took a consistent, unchanging position in their dealings with the prosecutors. Michael Milken proposed so many new strategies to his lawyers that Williams, exasperated, told him, “Mike, you keep trying to take your appendix out by yourself, you’re gonna cut your nuts off.”
In white-collar cases, defense strategy is often built on delay. In a joke that Milken liked, the Czar was riding his horse when it was spooked by a peasant. The Czar ordered his guards to kill the man. “If you let me live,” the peasant said, “I’ll teach your horse to talk. Just give me a year.” The Czar agreed and rode off. The peasant’s friends were dumbfounded; there was no way he could teach the horse to talk. “In a year, three things can happen,” the peasant explained. “The Czar can die. I can die. Or the horse can learn to talk.”
But other things happened. The government flipped witness after witness. Edward Bennett Williams died, and Arthur Liman left the defense to serve as chief counsel for the Senate’s Iran Contra investigation. The FBI paid a visit to Milken’s 92-year-old grandfather that devastated Milken. And then the prosecutors turned their attention to Lowell Milken. The government’s offer hardened: “a brother for a brother.” And with that, Michael Milken had his lawyers tell prosecutors he might consider a plea.
Plea negotiations are not hypothetical exercises. Milken didn’t understand that. But after three-and-a-half years of public battering, he still had no filter — every press leak, every negative article, every accusation cut like the first one. His lawyers understood what he didn’t: there is no white-collar defendant more vulnerable than a man who never dreamed he’d be one.
The prosecutors set a deadline. As the clock ticked down, no one on Milken’s defense team was sure what he’d decide. With five minutes to go, Arthur Liman called his client.
“Did you get any rest?” Milken asked.
“It’s time,” Liman said. “We have to decide.”
Milken rambled. There were pros and cons. The anguish. The desire to end to the struggle, the fear that everything he stood for would be tarnished. Liman covered his eyes with his hand. At last Milken said, “We’ll take the offer.”
It was not a good offer; it led to an astonishing fine and a ten-year jail sentence, much more money and time than it would have been if he had taken a plea earlier. But by then, it wasn’t humanly possible for Milken — or his lawyers — to go to trial. When I ran into Arthur Liman a few years later, I commented that this defendant seemed to have aged him. Liman agreed. And then he shook his head sadly, thinking of his former partner. “I have to think,” he said, “that Mike shortened Ed’s life by at least six months.”
After Trump’s incriminating tweets, his unhinged phone call to “Fox & Friends” and his dithering about an interview with Robert Mueller, the President’s lawyers might already have similar concerns.
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