The woman thought she was meeting a man who was going to pay her to have sex.
Instead, prosecutors said, he tried to kidnap her, forcing her into his car violently and driving off to a secluded location. The woman escaped by throwing herself out of the moving vehicle. The man returned later with a weapon to hunt her down, investigators said, but she was able to escape a second time.
The episode, in October 2018, was one of a several violent encounters between the man, Andrew Frey, and female sex workers, according to federal prosecutors in the Eastern District of New York.
On Friday, Mr. Frey, 54, of Coram, N.Y., was arrested and charged with two counts of attempted kidnapping and two counts of attempted sex trafficking.
Investigators who searched his home found rope, zip ties and manuals on tying knots, prosecutors said.
The facts of the case were reminiscent of an infamous Long Island mystery, when investigators found the bodies of four prostitutes and several other people near Gilgo Beach on Long Island’s South Shore starting in 2010.
Investigators believe that a serial killer was responsible for at least some of the unsolved murders, which have gripped Long Island for years.
Federal investigators are examining whether Mr. Frey had any connection to the Gilgo Beach murders, according to two people familiar with the case. There was no immediate indication that he had a role in the slayings, the people said.
Mr. Frey, who is married and has two adult children, worked as a manager at a Long Island company that makes aircraft equipment, according to prosecutors.
In seeking to detain Mr. Frey in custody before trial, prosecutors said that he had five previous convictions, including for felony drug possession, and a history of disobeying court orders.
Mr. Frey was expected to make his first appearance in Federal District Court in Central Islip on Friday. A federal defender representing him declined to comment.
If convicted on all counts, he faces at least 15 years in prison.
The arrest highlighted the dangers of sex work. Officials said that many women who do it are reluctant to report misconduct or violence against them to law enforcement authorities.
“It is likely that the defendant has victimized many others who have not yet reported their experiences to law enforcement,” prosecutors wrote in a court filing.
The indictment against Mr. Frey accuses him of two separate kidnapping attempts involving two female prostitutes, identified as Jane Doe #1 and Jane Doe #2. Both women escaped by jumping from his moving car, prosecutors said.
Another sex worker obtained a restraining order against Mr. Frey after he intentionally rammed his car into hers, prosecutors wrote in the court filing. He was also accused of violating the order by leaving her threatening voice mail messages.
William K. Rashbaum contributed reporting.