When Jessie Lee Herald fled the scene of a crash with his injured 3-year-old son late last year, authorities reached a breaking point with a man who had been in and out of jail and fathered seven children with six women.

A Shenandoah County prosecutor proposed a plea deal that would not only send the 27-year-old to prison, but would also require him to do something to ensure he would not have another child: Get a vasectomy.

Earlier this month, Herald agreed in exchange for some charges being dropped, touching off a debate about whether the novel punishment is appropriate or has set a dubious precedent that echoes the state’s dark history of forcibly sterilizing the mentally ill and mentally handicapped.

Shenandoah County Assistant Commonwealth’s Attorney Ilona White said she came up with the idea after looking at Herald’s criminal past.

“After reading the files and looking at the transcripts, it really did seem like it would be in the best interest of the Commonwealth,” White said.

Jessie Herald has agreed to have a vasectomy as part of a plea deal in a child endangerment case. (Shenandoah County Police/Via AP)

Charles Ramsey, Herald’s attorney, said it was a difficult decision for his client.

“His decision to accept the unusual offer was based on his desire to get home to his family as soon as possible,” Ramsey wrote in a statement. “He and I discussed several possibilities, and in the end, we felt that accepting this offer provided the most likely way to accomplish the goal.”

But Steven D. Benjamin, a Richmond lawyer and former president of the National Association of Criminal Defense Lawyers, said prosecutors shouldn’t force defendants to weigh prison against life-altering surgery. He was speaking generally, not about Herald’s case in particular.

“If the state can offer leniency in exchange for the loss of bodily function, where should the line be drawn that cannot be crossed?” Benjamin wrote in an e-mail. “When does negotiating the loss of a body part become unconscionable?”

Benjamin said plea deals involving such surgery reminded him of the 1924 “Virginia Eugenical Sterilization Act,” which allowed the state to sterilize more than 7,000 people in mental institutions who were deemed unfit to reproduce. The law was repealed in 1979 and victims are seeking reparations.

Herald’s case, first reported by the Northern Virginia Daily, began in December, when he crashed his car on a Shenandoah County road, according to a police report. A witness said Herald got out of the car with the 3-year-old and fled in a second car.

Herald’s wife told police that he brought the boy back to their Edinburg, Va., home. Officers found the child there, suffering from minor injuries and with glass in his diaper, according to the report. The boy was taken to the hospital, and Herald was later arrested.

Under the terms of his deal with prosecutors, Herald pleaded guilty to felony child endangerment, felony hit-and-run, and misdemeanor driving on a suspended license. He also agreed to undergo the vasectomy surgery within one year of getting out of prison on a four-year sentence.

He must not have the vasectomy reversed while he is on probation, and he has to pay for the operation, which could cost as much as $1,000.

In exchange for the conditions, prosecutors dropped two charges: failure to secure medical attention for a child and driving after the forfeiture of a license.

The case was just Herald’s latest brush with the law. He pleaded guilty to felony hit-and-run in 2007 for crashing his car after huffing an aerosol can, according to court records. He was found guilty of unlawful wounding for beating up another man the next year and was found guilty of possessing cocaine in 2012.

Herald, who occasionally works as a roofer, disputed the notion that he is not adequately involved in his children’s lives in a short statement released by his attorney.

“I think a lot of people have the wrong idea about who I am,” the statement read. “I do spend time with my kids and I do support my kids.”

Herald’s wife, Cassandra Herald, the mother of the 3-year-old, said he is a good father and husband who agreed to the plea because he feared a long prison term.

“I don’t think it’s fair to the both of us because we want to have more children,” she said. The other women with whom Herald has children were not listed in court papers.

Del. David B. Albo (R-Fairfax County), former head of the State Crime Commission, rejected comparing Herald’s case to forced sterilization.

“He’s volunteering to do it,” Albo said. “I don’t think [a vasectomy option] should be in the law, but if the guy wants to do it, I’m happy to let him do it. He’s got a responsibility to take care of those seven kids.”

A handful of prosecutors, defense lawyers and public defenders said they could not recall another case in the state in which a vasectomy had been part of a plea deal. Lawyers said there was nothing illegal about it because prosecutors and defendants have wide latitude to set the terms of a deal.

“You can make virtually anything a condition of probation as long as it doesn’t offend morals,” said Todd Petit, the Fairfax County public defender.

Still, Fairfax County Commonwealth’s Attorney Raymond F. Morrogh said he would never consider offering a plea deal that included a vasectomy.

“I see my role as enforcing the law and protecting the people through the fair administration of justice,” Morrogh wrote in an e-mail. “I leave moral bankruptcy and general lack of character to a higher authority.”

Benjamin said the goal of punishment is to deter similar criminal conduct in the future, so he wondered how a plea deal involving a vasectomy would do that. After all, he said, fathering children is not illegal.

Arlington County Commonwealth’s Attorney Theo Stamos said it is unwise to judge a plea deal from the outside — only prosecutors and the defendant know all the factors that were involved in the decision. Unlike Benjamin, she thought the punishment did fit the crime.

“Albeit it’s very unusual, there is some connection between number of the children this man had and his ability to care for them,” Stamos said. “I have a real hard time with people who have not been involved in negotiations of a case calling into question the motives of people involved in the case.”

Jennifer Jenkins contributed to this report.