Gwenda Blair is the author of The Trumps: Three Generations of Builders And A President and an adjunct professor at Columbia University Graduate School of Journalism.

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 countersuit, 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.

It’s been close to half a century since Trump retained Cohn (and more than 30 years since the iconic fixer, who died in 1986, performed an act of legal brutality for Trump). But at nearly every stage since then, Trump has hired a no-holds-barred lawyer to make a problem disappear. When he had to squeeze extra floors into a new building, he called Sandy Lindenbaum, a zoning-law guru who called himself “the last of the gunslingers”; when he needed the New Jersey Casino Control Commission to see things his way, he turned to Atlantic City fixture Nick Ribis; when he wanted to divorce Ivana (and, later on, her successor, Marla Maples), he retained Jay Goldberg, a self-described “killer” who says he can “rip skin off a body”; when it was tax time, he reversed decades of bragging about his billions and had tax attorneys say his properties were worth only a fraction of what he had publicly proclaimed (an ongoing tax appeal in Chicago declares Trump Tower Chicago “a failed business”); when he was in the market for a troubleshooter, he hired Michael Cohen, who has threatened journalists who’ve written about Trump with bodily harm. In the summer of 2015, Cohen told a Daily Beast reporter to “tread very fucking lightly, because what I’m going to do to you is going to be fucking disgusting,” and last fall he told Vanity Fair he’s “the guy who would take a bullet for the president.”

Perhaps most important, whenever Trump has seen anything that he thinks poses the slightest risk to his business or his reputation, he has sicced a lawyer on the offending party. Often such threats arrive in the form of a letter on heavy, cream-colored stationery, adorned with an embossed gold T and declaring that unless the addressee ceases and desists from all objectionable behavior, the Trump Organization intends to pursue said person to the full extent of the law, i.e., sue his or her pants off. I know. I got one of those missives when I published my book.

Sometimes, as in my case, the threat is all that happens. Other times, an actual lawsuit ensues, as when Trump retained attorney Marc Kasowitz to sue journalist Tim O’Brien for $5 million, claiming O’Brien libeled the notoriously image-conscious developer by asserting Trump was worth much less than he claimed. (They settled out of court.) And in still other cases, there has been a nondisclosure agreement, such as the one Cohen arranged for porn star Stormy Daniels (née Stephanie Clifford) after she claimed to have had an affair with Trump. According to an ongoing USA Today tally, as of April 2018, the Trump Organization has been involved in more than 4,000 lawsuits, far more than any other real estate developer—or any president, for that matter.

Apparently, after entering the White House, Trump felt entitled to the same robust legal protection that he enjoyed in his 26th floor office at Trump Tower. But things haven’t worked out that way. What Trump might euphemistically call “negotiating” in a boardroom runs the risk of becoming criminal obstruction when it’s done in the Oval Office. Unlike the lawyers Trump retained in New York, lawyers who work for the federal government aren’t his employees and can’t automatically cover for him when questions arise. He discovered this the hard way when Attorney General Jeff Sessions, once his most ardent supporter in the Senate, recused himself from the Russia investigation, paving the way for the special counsel investigation that continues to cloud the Trump administration. The lesson recurred when then-FBI director James Comey declined to swear loyalty or to let then-national security adviser Michael Flynn, accused of having lied about his contacts with Russians after Trump’s election, off the hook. Now Comey’s calling the president “morally unfit” in TV interviews to promote his book.

And there’s a corollary: Even Trump’s private lawyers don’t have the maneuvering room they had in the past. Last summer, Kasowitz had to step aside after laying into a critic with a profanity-filled email. John Dowd, whom Trump hired after being told he needed a Washington defense lawyer for the Russia investigation, has quit because he was being sidelined by other White House advisers. And despite Trump’s claim that plenty of lawyers and “top law firms” want to work for him, a growing number have passed on a chance to represent a client who contradicts them in public, changes his story repeatedly, expects them to lie and has a history of stiffing his employees.

Then again, perhaps Trump has come to the right place after all. According to the American Bar Association’s ABA Journal, Washington has a mind-boggling 773.8 registered lawyers per 10,000 residents (almost nine times as many as the second-most densely lawyered-up place in the nation, New York state, which has 88.7 registered lawyers per 10,000 residents). Surely at least one of them is willing to sacrifice reputation, sanity and perhaps a paycheck to defend the man who was elected to lead the country less than a year and a half ago. But it’s unlikely Trump will ever find another one willing to take out a home equity loan—and risk prosecution for bank fraud—just to spare his boss from an embarrassing sex scandal.