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RUTLAND — A Vernon man who has been charged with murder on the high seas in the death of his mother pleaded not guilty Wednesday in federal court and was ordered held pending a detention hearing May 16.

On May 2, a federal grand jury sitting in Rutland returned a sealed indictment, charging Nathan Carman, 28, with three counts of mail fraud, four counts of wire fraud and one count of murder on the high seas. If convicted of murder, he could be sentenced to life in prison. Each of the fraud charges carries a 10-year sentence.

In court documents filed after his arrest in Vernon on Tuesday, the U.S. Attorney’s Office for the District of Vermont states Carman had killed his grandfather, John Chakalos, in 2013, and his mother, Linda Carman, in 2016, to gain access to his grandfather’s estate, valued at tens of millions of dollars.

On Wednesday, Carman shouted “not guilty” in the direction of reporters who had asked him on his way into the courthouse whether he killed his mother.

“Carman killed strategically to achieve his goals,” states a motion for detention filed with the federal court on Wednesday morning. Assistant U.S. Attorneys Nathanael Burris and Paul Van de Graaf wrote that Carman poses a flight of risk, and that he is a danger to the community, and therefore should be held pending trial.

“For an individual who would kill his own family members, nothing is off the table,” states the motion. “Carman is alleged to have killed for money, and there is no reason to believe he would not also kill to gain advantage in a criminal case, particularly to avoid the possibility of life imprisonment.”

The motion for pretrial detention also notes that Carman had been treated for mental illness since he was 5 years old. Carman, who was diagnosed with pervasive developmental disorder, was medicated from the time he was 7 years old until he was 17, but has refused medication for the past decade.

“Records indicate that medication was, in part, intended to help manage anger,” states the motion. “At the age of 9, evaluators expressed concern about Carman’s ‘social difficulties’ and ‘explosive rages,’ highlighting episodes ‘in which he can become aggressive.’”

Carman, who has been unemployed for years, the federal attorneys wrote, also does not appear to have any meaningful community ties.

“He has limited human connections and little personal interaction with other people. ... Carman’s history and characteristics include the obvious fact that, in addition to having little or no human connections, he has little or no empathy for others.”

A mental health expert who evaluated Carman in 2003 said he exhibited “a highly unconventional problem solving style that is often not the most socially appropriate. ... He tends not to consider others in his problem-solving strategy, but appears to rely on immediate need gratification. That is, his self-interests almost always override the interest of others, regardless of the outcome.”

In 2011, after an emergency evaluation “after a tumultuous incident at his school,” Carman was diagnosed with potential mood and psychotic disorders, states the motion.

“Doctors noted that Carman had a history of hostility and aggression, and cautioned about the possible emergence of schizophrenia in the future.”

The attorneys recommended Carman receive “a proper diagnosis” before the court even consider releasing him into the community.

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Even though it has been cited repeatedly in court documents, Carman has not been charged with murder in the federal indictment for the killing of John Chakalos, whose estate was valued at more than $40 million and who had a mansion in Chesterfield, N.H.

“Carman has a history of involvement with firearms, including the Sig Sauer rifle he purchased in New Hampshire and used to kill his grandfather in Connecticut,” restated the motion for detention.

Police in Windsor, Conn., tried to obtain an arrest warrant to charge Carman with the slaying of his grandfather, but prosecutors rejected it. The murder weapon was never found.

In addition to his home in Windsor, Chakalos maintained the mansion in Chesterfield, which he adorned with thousands of dollars worth of Christmas lights each year.

In 1980, Chakalos built the 90,000-square-foot Spofford Hall, a substance use rehabilitation center that was shuttered in 1995 and was torn down in 2020.

Carman, who moved to Vermont in 2014, received $550,000 from his grandfather’s estate, spending much of it between 2014 and 2016.

By fall 2016, he was low on funds, and he arranged to go on a fishing trip on his boat, the Chicken Pox, with his mother.

“Nathan Carman planned to kill his mother on the trip. He also planned how he would report the sinking of the Chicken Pox and his mother’s disappearance at sea as accidents,” states an indictment filed Tuesday. “After leaving the marina, Nathan Carman killed his mother, Linda Carman, and eventually sank the Chicken Pox.”

Carman was found adrift in a life raft alone on Sept. 25, 2016, by the crew of a commercial ship.

Prior to setting sail on Sept. 18, 2016, with his mother from Ram Point Marina in South Kingstown, R.I., Carman told her they would be fishing near Block Island, returning home by noon the next day.

Little did Linda Carman know, her son had “altered the Chicken Pox in several ways, including removing two forward bulkheads and removing trim tabs from the transom of the hull,” states the indictment.

“All this made the boat unseaworthy,” said David Farrell, an attorney for the company insuring the Chicken Pox, in 2017. Carman’s claim for insurance reimbursement for the loss of his boat was denied by a Rhode Island judge.

Participants in the multiyear investigation of Carman included the Federal Bureau of Investigation, the U.S. Coast Guard, the Bureau of Alcohol, Tobacco, Firearms and Explosives, the Connecticut State Police, the Windsor Police Department, and the South Kingstown Police Department.

The Associated Press contributed to this report.

Bob Audette can be contacted at