[...]Den Hollander, a self-described “anti-feminist” lawyer [...] was known for his misogynistic tirades and the dozens of lawsuits he filed, many frivolous. A Manhattan judge dismissed one of them in May, and a few weeks later, a federal judge in New Jersey named Esther Salas canceled a scheduled hearing in a different suit.

The delay followed years of resentment that he had harbored against Salas over his unfounded claim that she was moving the case too slowly. That, in turn, built upon a lifetime of seething hatred toward women: He accused his mother of preventing him from having a girlfriend, and his ex-wife of marrying him only to obtain a green card.

Den Hollander’s rage turned to violence this month when he showed up at Salas’ home in New Jersey posing as a FedEx deliveryman and opened fire, killing her 20-year-old son and wounding her husband, investigators said. She was not harmed.

[...]Hours after the shooting in New Jersey, police found Den Hollander’s body off a road in upstate New York with a single gunshot to the head.

In his nearby rental car, investigators found a list naming more than a dozen possible targets, according to people briefed on the investigation. Aside from Salas[...], the list included the names of three other female judges and two oncologists, at least one of whom had treated Den Hollander.

An examination of Den Hollander’s life shows how he represented the most violent elements of a male supremacist movement whose discourse online has become increasingly threatening toward women.

He made his views clear in thousands of pages of writing. In his final months, he uploaded the last version of his autobiography, a 1,698-page manifesto that ended with an ominous epilogue about his determination to fight “feminazis” until his last breath.

His beliefs swirled between the worlds of self-proclaimed anti-feminists and men’s rights activists. He ranted about what he perceived to be gender discrimination against men in family courts and other institutions, a focus of men’s rights activists, but also wrote blog posts calling for women to be killed.

After a contentious divorce in 2001, Den Hollander began using the court system to address his grievances, suing nightclubs for advertising ladies’ nights discounts and Columbia University for having a women’s studies program. When he lost in court, as he almost always did, he would sometimes respond with lawsuits targeting the opposing lawyers personally — and even once sued a judge who had ruled against him.

[...]Den Hollander’s turn to violence appeared to be years in the making. In his autobiography, he mused about killing his mother and about sexual violence against a female judge in his divorce case.

[...]Den Hollander grew up in Midland Park, New Jersey, a middle-class town about 25 miles northwest of Manhattan, and had a loathing for his mother, clinging to grudges against her. In his autobiography, he claimed that she told him she wished he had never been born and that she would not let him have girlfriend or learn to play a musical instrument.

Den Hollander described getting in trouble in the third grade after trying to forcibly kiss two girls in his class, a pattern that would continue throughout his life. He later wrote that he was kicked out of a martial arts academy for “flirting” with women.

[...]In 2000, Den Hollander married a Russian woman, Alina Shipilina, in Moscow and returned to New York with her later that year.

The marriage quickly fell apart. He filed for divorce in 2001, accusing his wife of being a prostitute and of duping him into marriage to obtain a green card. She accused him of publishing her diary and naked photos online, citing an incident in which he threatened her with a gun, according to a complaint she filed that was posted on Den Hollander’s personal website.

[...]The divorce consumed him. He failed in his effort to seek an annulment to invalidate the marriage. Standing on the courthouse steps in New York after a divorce hearing, his devastation turned to hatred, he wrote in his autobiography. He said he wanted to bomb a feminist organization.

“Finally,” he wrote, “I knew my real enemies, the ones who plotted my destruction from birth, the ones who smiled so sweetly through their blood red lips — dames.”

[...]His unorthodox legal battles gained Den Hollander appearances on The Colbert Report and Fox News, but his notoriety alienated him from mainstream clients. In recent years, he took contract assignments helping big law firms review documents. One job paid $31 an hour.

He filed for bankruptcy in 2011 and frequently bemoaned his declining income. At a hearing in 2018, he seemed embarrassed by his status, telling the judge, “I get by doing the lowest of lowest of legal work, called document review.”

A legal services firm, Epiq Systems, fired Den Hollander in 2016 after he called another office worker an “illegal,” according to a lawsuit he filed against the company. A spokeswoman for Epiq confirmed that Den Hollander was terminated, without elaborating.

Later that year, he made calls for the Trump campaign as a volunteer, according to his autobiography. He said he was drawn to Donald Trump’s views on immigration.

An official with the Trump campaign said, “We don’t know anything about him, but the crimes in this case are horrific.”

In 2015, in his suit challenging the constitutionality of the male-only military draft, Den Hollander represented a woman who wanted to enlist. It was a legal cause supported by women’s advocacy groups, but Den Hollander had a different motivation. He wrote in his autobiography that women should “finally know not just the benefits but also some of the real hell of manhood.”

When the case was assigned to Salas, he wrote that he was initially attracted to her and wanted to ask her out. Later on, he called her “a lazy and incompetent Latina.” He claimed that she had worked for organizations “trying to convince America that whites, especially white males, were barbarians.”

[...]In one of Den Hollander’s last court appearances, a federal judge in Manhattan ruled against him at a hearing in February 2018. Den Hollander became angry, and the judge urged him not to take the ruling personally.

“It was a pleasure appearing before you, Your Honor,” Den Hollander told the judge, “but it is always personal.”