(CNN) He loaded the barrel, authorities said. Then he showed his wife how to position the rifle and called her "chicken."
In the end, she pulled the trigger.
Now, nearly six decades after the landmark conviction of a Massachusetts man in his wife's self-inflicted killing, a judge in the same state is weighing the fate of a woman accused of encouraging her boyfriend via text message in 2014 to commit suicide.
Michelle Carter, now 20, faces the same charge -- involuntary manslaughter -- to which Ilario Persampieri pleaded guilty in 1958. Prosecutors argue Carter's texts to Conrad Roy III, then 18, provide overwhelming evidence that she secretly urged him to kill himself.
"You need to do it, Conrad," Carter told Roy in a text message hours before he died, court documents show. "No more pushing it off. No more waiting."
Carter has pleaded not guilty, arguing that Roy was deeply depressed over his parents' divorce and a victim of physical and emotional abuse who was on a "path to take his own life for years." Carter also points to text messages she sent urging Roy to seek professional help.
Still, prior cases, the Persampieri conviction chief among them, suggest Carter's remote goading of Roy may have been criminal, legal experts told CNN.
"Persampieri is a huge case here because the court permitted the involuntary manslaughter charge where a defendant was present in the room during the suicide, encouraged the act, and dared her to do it," CNN legal analyst Danny Cevallos said via email.
Prosecutors must prove that Carter's actions directly caused Roy's death from carbon monoxide inhalation, though not that she acted intentionally, Cevallos said. If convicted in juvenile court, where she's being tried because of her age at the time of the alleged crime, Carter could spend 20 years in prison.
"The wrinkle here is whether she coerced him or pressured him into doing something that he wasn't in a position to rationally and autonomously decide to do because he was in such a depressive state," said Daniel Medwed, professor of law and criminal justice at Northeastern University.
"It's a square peg in a round hole," he said. "It's not a perfect fit for manslaughter."
The virtual nature of Carter and Roy's exchanges also could pose a challenge for prosecutors, legal experts said.
At one point, Roy got out of his truck and spoke to Carter for more than 40 minutes by phone, telling her that he was having second thoughts about taking his life, prosecutors said. But she told him to get back into the car, which was filling with deadly gas, documents show.
"Prosecutors may have a problem because he was 30 miles away, and he made decision to get back in the car," Medwed said.
The texts that led up to teen's suicide: Read them here
That key detail could prove critical to future cases.
"This is a seminal case, and one that has implications for electronic communication in the future," Cevallos said. "Courts are comfortable finding liability when the encourager is in the same room, but what if they are online?"
Some experts likened Carter's arm's-length exchanges with Roy to methods employed by Dr. Jack Kevorkian, who famously helped terminally ill patients kill themselves. Known as "Dr. Death," Kevorkian usually left poison near his patients, who administered it themselves.
Though critical differences surely exist -- Kevorkian was a medical professional who advocated the "right to die" for willing patients, while Carter was a teenager whose then-boyfriend's state of mind at the time of his death remains unclear -- both cases raise questions about what it means to help end a life.
Bolstered by Kevorkian's mounting claims of assisted suicide, Michigan lawmakers in 1998 made it a crime to force or coerce someone to commit suicide.
"These laws had to come about because when (Kevorkian) presented a bottle of poison for someone to take, he technically didn't kill them because they killed themselves," said Kari Hong, assistant professor of law at Boston College.
Kevorkian ultimately was found guilty of second-degree murder in 1999 after he personally injected a Michigan patient with lethal drugs. The videotaped death was broadcast by a network television news program.
Massachusetts has no law against assisted suicide, experts told CNN, noting that the Carter case could push lawmakers to act.
"If this is a moral problem, this is a problem for the legislature to fix," Hong said. "It's not the place for the judge to expand the law."
Either way, the result of Carter's case is likely to be controversial -- and a catalyst for lawmakers, Medwed said.
"Regardless of the outcome," he said, "I would be shocked if I didn't see legislation in the Massachusetts legislature next term."