Roy Den Hollander sounded bitter and angry when he bumped into a former rugby teammate in December at a library in Manhattan. He said he was so sick from a rare cancer that he could die at any moment, wondering aloud if he should sue his doctor for malpractice.
Things kept getting worse for Den Hollander, a self-described “anti-feminist” lawyer who 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.
Days before, Den Hollander, 72, had traveled by train to San Bernardino County, California, where he shot and killed a rival men’s rights lawyer at his home, authorities said.
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 and the rival lawyer, 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.
But by the end of his life, he was a man alone, facing terminal cancer, financial instability and a growing ostracization from the legal community and advocates for men’s rights, according to his writings and interviews with a dozen people who spoke with him in the past four decades.
“It really appeared to be a classical story of someone who felt scorned but then took it to a delusional, psychotic level in his response to it,” said Nicholas Mundy, the divorce lawyer who represented Den Hollander’s ex-wife.
When Den Hollander felt aggrieved, Mundy said, “he stopped at nothing to harass you and make your life miserable. He was like the Terminator.”
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.
During his divorce proceedings in 2001, his wife accused him of threatening her with a gun.
Den Hollander had long harbored a grudge against Marc Angelucci, the rival lawyer who served as vice president of the National Coalition for Men, a men’s rights group. Last year, Angelucci won a major victory in a lawsuit he brought challenging the male-only military draft, an issue that Den Hollander believed belonged only to him.
After Angelucci filed the lawsuit in 2013, Den Hollander called the coalition’s president and threatened violence. Den Hollander was then kicked out of the group.
Den Hollander shot and killed Angelucci, 52, on July 11 at his home in San Bernardino County, authorities said.
Den Hollander had brought a lawsuit in New Jersey similar to Angelucci’s that was pending before Salas. In his autobiography, he complained about delays in the case and appeared to be jealous of Angelucci’s victory. Last month, Salas had canceled a hearing in the suit that had been set for June 25.
In both the New Jersey and California shootings, the gunman wore a uniform resembling a FedEx driver, according to people briefed on the investigation. A spokesman for FedEx has said the company is cooperating with the inquiry.
In his autobiography, Den Hollander wrote about impersonating a FedEx delivery man on the phone when he was stalking his ex-wife after their divorce to figure out when she would be home.
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.
After graduating high school in 1965, he briefly attended the University of Colorado and later took courses at Columbia University, but it was not clear if he ever received a bachelor’s degree. He graduated from the George Washington University Law School in 1985 and received his MBA from Columbia Business School in 1997.
During this period, he avoided the Vietnam War draft and drifted between jobs, working as a local news reporter and for political campaigns in New York, according to his resume.
His many degrees and former employers created a veneer of respectability. Later in life, he sometimes brokered introductions with other lawyers by citing the fact that he once worked as an associate at Cravath Swaine & Moore, one of the most prestigious law firms in New York. (A spokeswoman for Cravath did not respond to a request for comment, but two lawyers confirmed working with him there in the late 1980s.)
He then moved to Moscow, a turning point in his life. In 1999, he was hired to work in the Moscow office at Kroll Associates, a corporate investigations firm.
Joe Serio, who helped him transition into the job as his replacement, said Den Hollander, who was in his early 50s at the time, talked openly about “keeping women in their place” and pursuing much younger women. He was obsessed with his own appearance, Serio said, dying his hair to look younger.
A spokeswoman for Kroll did not respond to a request for comment.
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.
At the time of the divorce, she was 25 and he was 53, according to the records posted on the site. She did not respond to requests for comment.
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.”
For years afterward, the subject of his ex-wife came up constantly, according to four people who recall the conversations.
After his divorce, Den Hollander’s legal crusade escalated, and he started filing a flurry of federal and state lawsuits. He often identified himself in court filings as an anti-feminist and a men’s rights lawyer, but some cases seemed to have no ideological purpose — like a lawsuit he filed in 2013 accusing the MTA of overcharging for MetroCards.
In 2007, he sued an upstairs neighbor in his Manhattan building, complaining of excess noise. After a routine court hearing in the case, Den Hollander chased the neighbor’s lawyer, Paul Steinberg, down a hallway and grabbed him from behind. They ended up scuffling on the floor, Steinberg said.
That night, Steinberg filed a complaint with the court and cited Den Hollander’s misogynistic blog posts in arguing for extra security, “particularly when there are factors (such as a female judge) which may trigger unpredictable behavior by Den Hollander,” according to a copy of the complaint provided to The New York Times.
Another female lawyer who had faced off against Den Hollander said a male colleague, after reading Den Hollander’s violent blog posts, once accompanied her to court in order to sit next to Den Hollander and create a physical shield for her.
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.”
The lawsuit is still pending and on Wednesday was assigned to a different federal judge in New Jersey.
In late 2018, Den Hollander received a diagnosis of mucosal melanoma, a severe form of cancer, he wrote.
It seemed that one of Den Hollander’s few remaining joys was playing rugby, which he said he originally joined to “keep myself in shape for the girls.”
The rugby teammate who saw him in December, when he sounded bitter, said he also chatted with Den Hollander in a short phone call during the pandemic. Den Hollander did not elaborate on his health but said he appreciated the call, recalled the teammate, who spoke on condition of anonymity.
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.”
This article originally appeared in The New York Times.
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