Trump’s Pit Bull Lawyer Would Mostly Rather Settle

In his first public appearance as President Trump’s lead outside counsel, Marc Kasowitz, a 65-year-old New York civil litigator, came out in his signature tailored suit and coiffed silver hair and proceeded to do what Trump’s lawyers generally do: swing wildly with roundhouse punches. Ex–FBI head James Comey? A leaker who defamed Trump and should be investigated. Comey’s testimony? Total vindication for Trump.

The next day, a slew of media outlets reported that Kasowitz planned to file complaints against Comey for his leaks of supposedly “privileged information” — the memos he’d written to keep a record of his meetings with Trump. Over a month later, no such complaint has been filed. Instead, Kasowitz himself now faces an ethics complaint for suggesting White House staff didn’t need to bother with getting their own lawyers.

A slick litigator, Kasowitz might seem straight out of the mold of the Trump Lawyer, who, as the New York Times’ Jonathan Mahler puts it, “fight[s] — sometimes in courtrooms, but mostly on TV.” In this, Kasowitz, who misspelled “president” in his statement on Comey, hasn’t been especially adept.

But as the Russia investigation, which now has dragged in Donald Trump Jr. with the latest revelations of Kremlin-connected meetings, continues, Kasowitz’s role is likely to expand. He may have stumbled in the eyes of the press, but his main function in the investigations is likely to be behind the scenes, negotiating with prosecutors. His expertise is not in keeping his client in the news. It is putting together the deals that end their legal problems.

Kasowitz, known as “Kas” inside his firm, has done plenty to foster the brawler image. In the fifteen-plus years of work Kasowitz has done with Trump, he’s shown a particularly rough side, indulging in Trump’s suing-as-punishment strategy. On Trump’s behalf, he sued journalist Timothy O’Brien for defamation, claiming O’Brien had understated Trump’s wealth. That suit was dismissed. So was one in which Trump sued business partners for not getting enough money in a property sale, though it was then considered the largest land deal in New York City history. Kasowitz has proved his tough-guy bona fides to Trump.

But the bare-knuckles bravado is also a cultivated persona. The son of the owner of a scrap-metal business, Kasowitz went to Yale University and Cornell Law School. He worked at the white-shoe firm of Mayer Brown before building his commercial litigation outfit — where he’s known as the “benevolent dictator” — from the ground up. The fierce image has been key to the success of his brand: Last year the firm of more than 250 lawyers grossed over $200 million. “He’s a showboat, he’s flashy; he’s basically like Donald Trump, if Donald Trump was actually really smart and accomplished,” said a former attorney at Kasowitz’s firm. All that bluster usefully disguises Kasowitz’s biggest strength and greatest asset to Trump: He’s really good at settling.

“The brawler costume is misdirection,” said James Moriarty, who was Kasowitz’s opposing counsel on a massive product liability suit. It ended with Kasowitz helping to broker a $1 billion agreement for his client the Celanese Corporation, then one of the biggest consumer fraud settlements in U.S. history. “What he is is a deal-maker and a strategic thinker. His client was in a world of trouble, and he pulled them out of the dirt.”

From the outside, Trump’s legal team can look like a collection of wrestlers in sharp suits — one colleague describes Kasowitz as “straight out of central casting for a New York lawyer.” Inside, though, each seems to have a different role to play. There is Donald McGahn, Trump’s White House counsel. A former Trump campaign attorney who has been described as an “iconoclast” and loyal to Trump, McGahn is tasked with protecting the office of the president and may not have the usual lawyer-client confidentiality privileges with Trump. There is Michael Cohen, once Trump’s frequent TV surrogate. His role, as one person who knows both Cohen and Trump explains, “is strictly dark ops, the things Trump can’t do. I don’t know if he’d even know how to start a lawsuit.” And to get Donald Trump out of complex legal tangles, there is Kas.

One line about Kasowitz that seems to appear whenever he’s written about, and even gets repeated in his own online bio, is that he’s the “toughest of the tough guys.” It originates in a 1997 American Lawyer quote from Don Barrett, who worked as Kasowitz’s opposing counsel on two massive product liability cases. What gets left out in the retelling is that Kasowitz ended up cutting deals with Barrett in the cases, settlements that Barrett still considers “win-win — his clients did well, but so did mine,” as he told the Voice.

Indeed, in 1995, sitting across the table from each other, Kasowitz and Barrett knocked out an industry-changing deal, one that set the foundation for Kasowitz’s then new law firm. Barrett was representing five state attorneys general who were suing large tobacco companies to recoup the billions of dollars states were spending on treating sick smokers. At the time, Kasowitz was representing Liggett, the smallest of the five major U.S. tobacco companies. Up to that point, Big Tobacco had a firm policy — it didn’t settle lawsuits. The suits from the attorneys general were a threat to the industry, and most immediately to Liggett, because it was smaller.

“Those suits could have wiped them out,” says Richard Daynard, a law professor at Northeastern University and chair of the school’s Tobacco Products Liability Project. “Get attorneys general in front of a jury saying it’s either your tax dollars or tobacco companies that are going to pay — that’s not a good place to be as a defense lawyer.”

Barrett said he told Kasowitz, “Look, if one company had the foresight to be the first settler, we could basically let them off scot-free.” Settlement negotiations, done in secret, started a week later and lasted for eight months, a fast clip for what had been years of fighting. “He’s hard and he’s fast — and he’s creative and thinks outside of the box,” Barrett said. “It was pretty tough negotiating, but we got it done.”

The settlement, signed off on in 1996, left other industry executives furious and blasting the deal. In the end, Liggett didn’t exactly get off scot-free. While the initial deal involved a modest amount of money — $5 million and 2.5 percent of Liggett’s profits for 25 years — it opened the door to a bigger settlement with 22 other state attorneys general. Liggett — still represented by Kasowitz — became the first tobacco company to admit that nicotine was addictive, cigarettes can cause cancer, and tobacco companies consciously marketed their products to kids as young as fourteen. Liggett also gave up internal documents incriminating the other tobacco companies.

While those bigger companies could hold out longer, Liggett couldn’t take the risk of giant verdicts that might leave it bankrupt. The deal kept the company afloat. Kasowitz had broken industry rank, turning on the big players to protect his client and in the process changing how the tobacco industry handled litigation. “We got the least important culprit to turn state’s evidence and give testimony against the really bad guys,” said Frank Kelley, attorney general of Michigan at the time. The four bigger companies, including Philip Morris and Lorillard, which together controlled about 98 percent of the U.S. cigarette market, agreed, a year later, to a settlement with the states — and a much more expensive outcome: annual payments, forever, with a minimum of $206 billion over the first 25 years. The industry as a whole also had to agree to stricter marketing rules — like no more ad campaigns featuring Joe Camel, the cartoon spokesman who appealed to kids.

“The Liggett settlements are Kasowitz’s most distinguished accomplishment,” Daynard said. “This is the guy who really figured out another way, figured out something that was thought, at that time, to be an unthinkable, impossible settlement.”

In the twenty years since the tobacco deal, Kasowitz has continued to be involved in numerous negotiated endings — the vast majority of cases in commercial litigation, Kasowitz’s specialty, end up settling, legal experts say. In 2014, he helped secure a $1.25 billion payout from Morgan Stanley on behalf of his client the Federal Housing Finance Agency, which sues banks over mortgage securities fraud; more recently, he helped negotiate a deal for Trump, the client who says he never settles, to pay out $25 million in the Trump University litigation.

A lawyer who has faced Kasowitz said that, like Trump, the litigator would be hard-pressed to see anything he’s worked on as a loss. In the world of legal settlements, everyone can claim victory, or keep all those details confidential.

“Look,” Daynard says, “if you want to settle a case favorably, of course you say, ‘I’m the toughest of the tough’ — you don’t say, ‘Oh, I’m the guy that settles cases.’ I don’t think Trump wants it broadcast around that he brought in Kasowitz to cut a deal with the special prosecutor.”