An Inwood attorney pleaded guilty Wednesday to relentlessly cyberstalking a former girlfriend, sending the victim hundreds of text, voice and email messages over nearly four years and creating online posts in which he threatened to hold the woman hostage and torture her.

David Waldman, 49, pleaded guilty in U.S. District Court in Manhattan to one count of cyberstalking. He faces a maximum sentence of 5 years in prison.

Waldman met the woman on an online dating site in late 2013, prosecutors said. They dated for four months before breaking up in March 2014.

Days after the breakup, Waldman began sending the woman, a banking executive, a barrage of rambling email and text messages in which he would intermittently threaten her life and accuse her of illegal behavior while also pleading with her to resume their relationship, charging documents show.

"Women like you come around once, twice, maybe three times in a lifetime," Waldman wrote in an April 8, 2014, email. "That means you are rare and valuable. And something to be kept and cherished. And cherished can mean held hostage and bound and gagged inside my apartment."

On April 30, 2014, Waldman was arrested by the Manhattan district attorney's office and charged with aggravated harassment. He was arrested a second time in December 2014 and charged with misdemeanor criminal contempt and stalking. Waldman pleaded guilty to the contempt charge and was issued a conditional discharge and ordered to stay away from the victim.

Despite the order of protection, the harassment continued, with Waldman using fake names and email addresses to threaten the woman and later creating blog posts targeting the victim, prosecutors said.

In the posts, Waldman would complain that he was the victim and that his ex-girlfriend had been diagnosed with bipolar and narcissistic personality disorder, had threatened his life and fabricated claims of childhood sexual abuse.

The threats continued through May 2018 when Waldman, using the pseudonym "Steve Wexler," sent the woman an email saying she should be killed. Waldman was arrested by federal authorities in June 2018.

Clay Kaminsky, Waldman's Manhattan-based attorney, declined to comment.

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