Trump’s Lifelong Addiction


It is a truth universally acknowledged that Donald Trump has a thing about women. In addition to his three wives, there are scores, perhaps hundreds, possibly thousands of women he’s hit on, dated, married, cheated on, employed, promoted, denounced and ridiculed.

But there’s another type of individual he has a thing for—some might even say it’s an addiction. And it’s a group that may be far more essential to his way of being: lawyers.

Most business executives tend to be lawyer-dependent, but for the better part of 50 years, lawyers have done everything for Trump except have his children. They have finagled unprecedented tax abatements, kept him going through multiple corporate bankruptcies (and out of personal bankruptcy), protected his finances from public scrutiny. They are so entwined with every aspect of his public and private life, it is unimaginable that Trump could have gotten anywhere close to where he is today without them. But now, in the aftermath of the FBI raid on the offices and residences of his most prominent personal attorney and fixer, Michael Cohen—he of the $130,000 pre-election payment to the porn star—the same techniques that Trump’s lawyers have employed for decades to smooth his business path are the very things that threaten to blow holes in his still-young political career. For perhaps the first time in his life, a lawyer has become Trump’s biggest problem instead of his salvation.

Trump inherited his love of lawyers from his father, Fred Trump. In the 1930s, the elder Trump began to put together what would be the first Trump real estate empire. While other builders were still reeling from the Great Depression, Fred had a secret weapon: a beneath-the-radar attorney named Bill Hyman who used pseudonyms, stand-ins at auctions, even dummy subsidiary corporations to avoid tipping off Brooklyn landowners who might have held out for higher prices if they knew Fred Trump was assembling packages of adjacent lots for large-scale housing developments.

Ever the apprentice, young Donald followed suit and lawyered up. But he wanted more than behind-the-scenes, Bill Hyman-style competence. He wanted someone who would get right up in an opponent’s face and blast away. His dream came true when Eugene Morris, who had represented his father, introduced Donald to Morris’ first cousin, the infamous Sen. Joe McCarthy’s lawyer, Roy Cohn, who had stood trial multiple times for bribery, perjury and extortion but had never been convicted. “I think Donald was attracted by the fact that Roy had actually been indicted,” Morris told me when I was working on a Trump family biography. The famously pugnacious Cohn told a reporter in 1980 that Trump called him “15 to 20 times a day, always asking what’s the status of this, what’s the status of that?”

In 1973, when the U.S. Department of Justice charged the Trump Organization with housing discrimination. Cohn hit back with a $100 million counter suit, the quintessential Cohn move of punching back harder. In the end, Cohn pulled off a wrist-slap settlement that spared Trump and his father from a guilty plea or any financial penalty. Over the next decade, Cohn used his mob connections to smooth the younger Trump’s relations with construction unions; inked a stingy prenuptial agreement with Trump’s first wife, Ivana; leaned on city politicians to favor Trump deals; traded favors in Atlantic City’s notoriously corrupt casino industry; and tried to strong-arm the National Football League into a merger that would give Trump a first-tier team at a fraction of the going rate.

Sometimes things have gone badly for Trump his football venture failed, and in an ensuing lawsuit, he received only a humiliating $3 in damages. But even when his ventures have tanked (Trump Air, Trump Vodka, Trump Mortgage, his casinos, the Plaza Hotel, Trump Soho Hotel, and a string of never-opened Trump-branded ventures in Argentina, Brazil and Canada, among other places), to all appearances, lawyers have kept him solvent.

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