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An influential lawyer at the Department of Health and Human Services who previously clerked for Samuel Alito before his time on the Supreme Court has a long history of anti-abortion extremism, including multiple arrests for harassing abortion providers, according to a new report from Mother Jones.

On Friday, Mother Jones reported that Matthew Bowman, a deputy general counsel at HHS—who also provided legal counsel to the Office of Refugee Resettlement as it tried to block migrant girls from accessing abortions—has a long history of harassing and targeting abortion clinics, providers, and patients. According to Mother Jones, Bowman had “at east fourteen run-ins with the law” between 1996 and 2001, including arrests during abortion protests. Here’s how Bowman spent his free time during law school, which he started in 2000:

According to police reports, he began approaching women as they parked outside Packard [Women’s Clinic, in Ann Arbor, Michigan], following them from their car to the clinic’s entrance and “harassing” them about abortion even if they asked to be left alone. In June 2002, a nurse at the clinic, Jill Toney, told police that Bowman had been following her “at a close distance” when she entered the clinic, calling her a murderer, telling her that she would go to hell, and placing flyers on her arm or in her pocket after she declined to take them. Toney had grown so frightened of him that she’d taken to asking a manager to escort her. Of all the demonstrators who regularly protested Packard, Bowman, she said, was the only one that made her feel “uncomfortable and intimidated.” Five other female employees at the clinic, Toney said, had also felt threatened by him. She said that in addition to videotaping patients and employees, sometimes concealing the camera in his car, Bowman had also begun recording employee’s license plates. Toney told police she only reported Bowman after enduring months of his behavior, in hopes that he would be prosecuted for harassment and intimidation. Local prosecutors decided Bowman’s behavior did not rise to the level of criminal harassment, but advised she speak with a lawyer about filing a civil claim. (It’s unclear if she did; Toney did not respond to requests to comment.)

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Bowman continued his anti-abortion harassment through law school, and clerked for several federal judges, including the ultra-conservative Samuel Alito, who went on to become a Supreme Court justice. In 2006, he worked at the right-wing Christian advocacy group Alliance Defending Freedom’s Center for Life, where he “continued to wage anti-abortion battles, successfully representing clients in cases opposing Obamacare’s birth control benefit, state abortion access laws, and laws relating to the expression of anti-abortion views,” Mother Jones reports.

As Brigitte Amiri, an American Civil Liberties Union attorney who represented the migrant girls seeking abortions while in in ORR’s custody, said: this history matters. “If Matt Bowman has a history of flouting the law with respect to his advocacy, then it should come as no surprise that he would flout the law when he was given a position of power at HHS,” she told Mother Jones.

Bowman’s history is striking, but his trajectory is not: it’s unsurprising that an anti-abortion extremist would find a comfortable home with judges and inside an administrations that supports extremist policy. That’s precisely how these pipelines work.