David Freedlander writes about politics and culture. He lives in New York.

The blog—now defunct—was called Underneath Their Robes, the poll was on “Superhotties of the Federal Judiciary,” and the winner in the female category was a New York judge named Kimba M. Wood. After that, things could have gone totally off the rails. The blogger behind the poll, a Yale Law graduate named David Lat, found himself on a panel a few years later with Judge Wood and braced himself for a lecture. She was a very senior jurist; he was an upstart who had named her a “bodacious babe of the bench.”

Instead, when Wood found out who he was, she tossed her head back and started cackling.


“That’s your website? What a hoot!” Wood told him.

As of this week, Wood sits at the center of the nation’s most important legal drama, deciding just how much attorney-client privilege President Donald Trump will be granted as prosecutors rifle through the files of his personal lawyer, Michael Cohen. Last week, federal officials seized papers, cellphones, a tablet, a laptop and a safe deposit box from Cohen’s office and hotel room. Cohen’s lawyers say that material is protected, and Wood is adjudicating their request. She is, friends and colleagues say, the perfect judge for the unfolding political drama that has washed up on the steps of the federal courthouse in Lower Manhattan, complete with porn actress Stormy Daniels showing up at a hearing.

As her response to the “superhotties” poll shows, Wood can laugh off inappropriate attention. And she’s been involved in some Trump-worthy coverage herself, with a husband who once got in trouble for anonymously sourcing a story about her in the New York Times—and whom she later left for Frank E. Richardson III, an ultrawealthy financier whose connections have made Wood a regular of the society pages and the black-tie gala circuit, a rarity among federal judges.

The Southern District of New York, where Wood presides, isn’t your average courthouse. It’s the main federal court in Manhattan, and its judges routinely end up in the news for hearing cases with famous or powerful clients. In her 30 years there, Wood has tried junk bond financier Michael Milken, Mafia soldiers and a group of Russian spies captured in an FBI counterintelligence operation. She became something of a tabloid sensation herself when her relationship with Richardson blossomed into a summer scandale in New York, earning her the moniker “The Love Judge.” And in one biographical tidbit that Trump could truly appreciate, a young Wood once spent a week working as a croupier, in bunny ears, at the Playboy Club in London.

So she’s used to the celebrity spotlight in a world in which it is increasingly difficult to draw the line between politics and entertainment. But she is also a profoundly moderate jurist, one known among her colleagues for a rare degree of thoughtfulness and restraint from the bench. And despite the anxieties of conservatives who know her from her failed nomination as attorney general for Bill Clinton, she’s originally a Reagan nominee.

And there’s one irony that might be a saving grace for Cohen and Trump. If anything, Wood has sympathy for defendants caught up in the criminal justice system. She has donated thousands of dollars to the Vera Institute for Justice, a criminal-justice reform nonprofit that focuses on ending mass incarceration; and as “soft on crime” as that may sound to conservatives, any skepticism she may have about prosecutors will work entirely in Trump’s favor.



***

Wood first came to the public’s attention in an embarrassing reversal when she was picked, in 1993, to be Bill Clinton’s attorney general. Wood was Clinton’s second choice. His first, Zoe Baird, had withdrawn her name from consideration when it was revealed that she and her husband had hired illegal immigrants as a chauffeur and a babysitter without paying taxes. Wood’s nomination flamed out next, when she revealed that she too had hired an illegal immigrant as a nanny. Although Wood had paid taxes on her household help, it was too close to the Baird situation for an administration struggling to find its footing.

The drama did not end there. Wood was married at the time to Michael Kramer, a Time Magazine political columnist who had golfed with candidate Clinton and written a glowing Man of the Year profile of him. When Wood’s nomination flamed out, the lead story in the New York Times quoted “a source close to Wood” who contradicted the White House version of events. “Basically, the White House concluded that the distinctions between Judge Wood’s case and Zoe Baird’s were too complicated to explain in a 30-second sound bite and that they were not going to expend any political capital doing it. But if you can’t make the distinction between somebody who did something wrong and somebody who didn’t, what good is the moral authority of the president?” the source said.

The “source close to Wood” was her husband, Kramer. His version was contradicted the next day by Wood’s own version in the paper, which stated that she felt “compelled to correct the impression” from the earlier story and backed the White House. Meanwhile, Kramer’s role as a political hatchet man on behalf of his wife set off an uproar at Time magazine.

Even before her brief political foray, Wood had cut an unusual figure in legal and political circles. Born in the tiny mill town of Port Townsend, Washington, Wood was named after a remote village in southern Australia that her mother noticed while flipping through an atlas looking for baby names. Her father was a speechwriter in the Army, and Wood grew up a girl of the globe, speaking French before she knew English. She went to the Sorbonne in Paris before transferring to Connecticut College, then to the London School of Economics, where she took a job at Hugh Hefner’s Playboy Casino, training as a croupier. She quit after six days, finding it “silly,” and soon left London, too, winding up at Harvard Law School.

Women were a rarity in the upper echelons of the New York legal world in those days, but Wood shot up the ranks, becoming an expert in antitrust—then one of the most prestigious areas of the legal profession—at LeBoeuf, Lamb, Leiby & MacRae, then a top New York law firm.

“My God—she was really, really good and really, really tough,” recalled Lloyd Constantine, then the assistant attorney general in charge of antitrust for New York state, who frequently found himself on the other side of the courtroom from Wood. “She just had this commanding presence—she was smart, she was good on her feet, eloquent, and extraordinarily beautiful.”

Wood has been slammed in right-wing circles in recent days not only for being a Clinton-administration nominee, but for having officiated at George Soros’ third wedding in 2013. Wood’s third husband, the financier Frank E. Richardson III, sat on an advisory committee for Soros’ Quantum Industrial Holdings, and the Hungarian-born financier was someone they would run into socially occasionally. (A court spokesman noted that Soros’ wedding was one of dozens she has performed in her career.) But Wood was originally a Republican nominee, named to the bench in 1987 by Ronald Reagan and New York Republican Senator Alfonse D’Amato, who both figured that because she was representing major insurance companies and other corporate interests against government efforts to break them up that she must be something of a free marketeer.

In one of the biggest cases of her career as a corporate lawyer, Wood represented Lloyd’s of London in an investigation by five state attorneys general who were examining whether it had colluded with other insurers to raise premiums and make some policies unavailable. Wood’s side won in lower courts until she was pulled off the case after her nomination to the federal bench. Prior to Wood’s confirmation hearing, a deputy attorney general in California accused Wood of obstructing justice, and submitted the objection into the official record. The claim was specious, and it’s a measure of the respect Wood had earned that two lawyers from the other side of the case—Constantine and New York Attorney General Robert Abrams, who had both opposed her in court—rushed to her defense, traveling to Washington to testify in her favor.

At her judicial confirmation hearing, friends of Wood’s from New York prepared her for the off-color remarks she might face from Senator Strom Thurmond, then in his 80s and with a reputation for making demeaning remarks around young and attractive women. Wood, according to Constantine, dismissed her handler’s concerns—Don’t you think I’m used to that kind of thing by now?—but in the end, Thurmond was a perfect gentleman. It was D’Amato who rumbled during the hearing, “Mr. Chairman, do not let the nominee's appearance deceive you. It is obvious that she is beautiful. It might raise questions in terms of her youth. How is this that someone so youthful in appearance should be placed before this committee as a nominee?"

Her friends were mortified. Wood scarcely registered the comment.



***

Once on the bench, most judges quickly establish a reputation that can be boiled down to a sentence by court-watchers. Neil Gorsuch, for example, favors limiting the power of the regulatory state; for Sonia Sotomayor, it is using empathy as a guiding light in interpreting the law.

“If I were the judge in the matter, I know what everybody would say: ‘Oh, it’s the “stop-and-frisk” judge—of course she is biased,’” said former federal judge Shira Scheindlin, who famously ruled in 2013 that the New York Police Department’s stop-and-frisk program was unconstitutional. “Kimba is not like that. She is not pro-plaintiff or pro-defendant. She is not to the right or to the left. She is very neutral and pragmatic.”

“You won’t hear from her an opinion that is groundbreaking for being completely novel,” said Judge Jed Rakoff, a fellow jurist on the Southern District and a law school classmate of Wood’s. “Her style is to hear both sides to achieve a balanced result.”

Current and former colleagues and other observers of the federal bench said much the same thing. “She doesn't need to eat the whole barrel to know it's not a pickle,” one lawyer told the Almanac of the Federal Judiciary, a line Lat quoted in his “Bodacious Babes of the Bench” poll. When she told lawyers for Michael Cohen that they had to reveal the name of his third client, who turned out to be Fox News host Sean Hannity, colleagues said they could hear her voice when they read how she rebuked them. “I understand that he doesn’t want his name out there, but that’s not enough under the law,” Wood told Cohen’s lawyers. “Withholding a client name is not in accordance with the law in this circuit.”

This wasn’t what Cohen’s legal team wanted, but it wasn’t a surprise to anyone, either: Every judge I spoke with said requiring his lawyers to cough up the name of Cohen’s client was a no-brainer. Any judge, unless she had her thumb on the scale for Trump, would have done the same thing. A slightly more difficult decision is whether or not to appoint a “special master” to oversee Cohen’s files that relate to Trump and might be protected by attorney-client privilege. Ordinarily, the government would designate a “taint team,” agents unconnected to the investigation to sift through the documents and determine which are protected and which aren’t. Wood has said that given the perception issues around this case, another approach may be warranted: a court-appointed “special master” to oversee that process. She has also rejected Cohen’s claim that all documents gathered by the FBI should be privileged—an overall approach that attests, observers say, to her concern about the appearance of bias, and her desire to take a slow and deliberative tack moving forward.

“It’s a 51-49 decision,” said one jurist. “There is no question the government taint team would be sufficient to achieve fairness, but the question is the perception of fairness, and because of the notoriety of the case the judge had to be aware of what would be perceived as fair.”

Finding a deliberate middle ground and protecting the reputation of the court have been hallmarks of Wood’s career. Wood was just 44 when she was sworn in as a federal judge, the youngest on the Southern District. A mere 2½ years later, she was handed one of the biggest cases of her era. Junk bond king Michael Milken was one of the highest-flying figures of 1980s finance, and his lawyer was Arthur Liman, a legal titan who had investigated the Iran-Contra affair and the Attica prison uprising. Milken had already pled guilty; Liman pointed to the tens of millions of dollars Milken had given to charity to argue for leniency. The audience in the courtroom gasped when Wood handed down her sentence: Ten years in prison, a term twice as long as many expected. She read a withering explanation of her decision from the bench.

“You were willing to commit only crimes that were unlikely to be detected,” Wood said. “Your crimes show a pattern of skirting the law, stepping just over to the wrong side of the law in an apparent effort to get some of the benefits from violating the law without running a substantial risk of being caught.”

Later, Wood reduced Milken’s sentence to two years for cooperating with prosecutors in other financial fraud investigations—setting off another uproar among those who wanted to see Wall Street wrongdoers pay dearly for their crimes. Ed Markey, now a senator from Massachusetts, but then a member of the House of Representatives serving on a subcommittee that investigated the scandals, called the decision “outrageous” and said it “sends exactly the wrong signal to Wall Street.”



***

The Milken trial was the first of many trials of national import that Wood would rule on. In 2010, she issued a “permanent injunction” against LimeWire, effectively shutting down the peer-to-peer file-sharing service. Also in 2010, she presided over the trial of 10 Russian spies living undercover in the United States whose story inspired the television show “The Americans.” She allowed protesters to sleep on the street in front of Gracie Mansion, the official mayoral residence, as a form of protest, even though lawyers for the city argued that it wasn’t protest so much as vagrancy.

If Wood was disappointed in not becoming Bill Clinton’s attorney general, she never showed it. Friends say that it was probably for the best that the retiring judge was never in that kind of political spotlight. “She loves being a federal judge. It suits her well,” said Judge Scheindlin. “I don’t think not being attorney general has been very disappointing for her.”

Wood doesn’t write for mainstream media publications, doesn’t lecture from the bench and doesn’t much take part in the social life of the federal judiciary, observers say. But the spotlight has found her regardless. In 1998, Richardson, a Harvard Law classmate of Wood’s was going through a messy divorce when his wife found diary entries of his liaisons with Wood, who was still married to Kramer. Nancy Richardson, a wealthy socialite, leaked the diary to the press in which Richardson described in painstaking detail his blossoming romance with the judge.

“Kimba that's something else ,” Richardson wrote in one passage that would earn Wood the tabloid nickname “The Love Judge. “[I'm] wild, wild, wild about her. Overwhelmed. No sense of reserve ... intoxicated by her body.”

When she returned to the bench after a summer recess, it was national news.

“Judge Wood Stays Calm (and Silent) Under Media’s Glare,” read a headline in the New York Times. “No wedding ring,” the report noted.

The resultant marriage to Richardson put Wood in a social stratum unusual for a federal judge. Richardson sat on the board of the Metropolitan Museum of Art, and the two are frequently photographed on the society pages together.

“I went down to Michael’s to lunch with a friend,” wrote the New York Social Diary in 2012. “In the bay behind our table were several Very Busy Ladies Who Lunch together about once a month; pals: literary agent Esther Newberg, Linda Fairstein, Faye Wattleton Lynn Scher, Kimba Wood, Jurate Kazickas, Lesley Stahl, Ellen Futter (I’m not sure she was present yesterday). I have no idea what they talk about but it would be interesting considering that these are some of the most dynamic/can-do/get-things done women in New York.”

“She is the perfect judge for this case,” said Constantine. “She knows who she is. She is straight-ahead. She isn’t affected by flattery, by cheers or by jeers. She is going to do a very good job on this Cohen matter. Kimba Wood is not going to try to please anybody.”