MIDDLETOWN, Conn. — By the time Nathan Carman was 17 years old, his mother feared that he suffered from paranoid delusions. Once, he called his high school’s vice principal “Satan,” and a secretary “an agent of the devil,” according to three people with knowledge of the episode.
It was the kind of troubling behavior he usually reserved for his mother, she wrote in an online posting desperately seeking a mental health facility that would provide her son “top-notch, effective care.”
Five years later, his mother, Linda Carman, is presumed dead after being lost at sea last month on a fishing trip with Nathan, who was rescued after more than a week on a life raft.
At the time of his outburst at Middletown High School, in April 2011, he was in anguish, his father said. His classmates either ignored or bullied him. His only friend, a horse named Cruise, had died. He loathed his diagnosis of Asperger’s syndrome, a high-functioning form of autism, and the way it set him apart.
Despite his struggles, he posed no threat, his father said.
“Talk and grief, that’s what it was,” his father, Earle Clark Carman, said in a recent interview from the Middletown home of his missing ex-wife. “There was no action.”
In the years that followed, criminal investigators would probe Nathan Carman’s teenage years, which included a hospital admission for psychiatric treatment. He was named in a police affidavit as a person of interest in the unsolved 2013 shooting death of his wealthy grandfather, John Chakalos, in his Connecticut home. Now, the 22-year-old is the subject of a multistate investigation into the circumstances of his mother’s presumed death, according to a police affidavit.
Carman, who lives in Vernon, Vt., has denied responsibility in both deaths and said he loved his mother and grandfather. He did not respond to repeated requests for comment.
“It doesn’t feel good to be bringing up everything that I went through with the loss of my grandfather now at the same time that I’m trying to come to terms with the fact that my mom is really gone,” he said during an earlier interview.
In interviews over the past week with about 20 people who know Nathan Carman or his family, a picture emerges of a bright but alienated young man with tightly held conservative beliefs, acutely conscious of his social struggles but unable to overcome them.
“I didn’t see him ever reach out,” said one high school classmate who, like most people who were interviewed, spoke on condition of anonymity to avoid public involvement in the high-profile case. “I would imagine, being in his shoes, that would be extremely painful.”
Some of Carman’s fellow students described him as smart and independent, with a passion for classroom debates about religion and politics. He was an easy target for bullies: Students gave him a hard time over his stiff demeanor, and his Asperger’s made social interaction difficult.
None of the classmates interviewed by the Globe could recall him ever having a friend. While a police affidavit said Carman “was capable of violence when his coping mechanisms were challenged,” classmates said he did not seem threatening, just painfully awkward. Two people recalled that he once got in trouble for bringing a pocketknife to school, though he was not aggressive with it.
Carman went out of his way to avoid conflict, students said. Once, when a student mockingly filmed him with his cellphone in class, Carman simply took the phone until a teacher arrived, another student said.
“I remember him in gym class,” another student said. “He was the guy that no one wanted on their team.”
Estranged from his peers, Carman forged a close bond with his horse, Cruise. When Cruise died in December 2010, a few months before his high school outburst, Carman was adrift.
“He was only 17. He had no friends,” his father said in a weary voice. “How do you protect him? If you don’t isolate him? And that’s even worse.”
Earle Carman said that Linda Carman made sure their son received a range of services, though Nathan was not always enthusiastic about the help.
“She always doted on him, took care of him,” the elder Carman said. “But he was resistant to it. The main thing is the label — autism. That drives him crazy. He’s so functional.”
The couple filed for divorce in 1998.
In an April 2011 posting in an online forum for people seeking answers to questions about mental health, a woman who identified herself as Linda Carman of Middletown, Conn., pleaded for advice. Details of the post were authenticated by several people with knowledge of the incident at the school and the circumstances surrounding it.
“Yes, he is a complicated mess,” she wrote. He was suffering from “paranoid delusions” and “religious idiocy,” she wrote, and had stopped taking his medication.
A short time after the episode at school, Nathan Carman was admitted to Mount Sinai Rehabilitation Hospital for psychiatric treatment. But the two people who were closest to him in the world — his mother and his grandfather — were split on his care. The two got into a physical altercation in the hospital waiting room, and Linda Carman was arrested, though the charges were later dropped.
In her online posting, Linda Carman lamented that her son had allowed his grandparents to visit him for hours at a time at the hospital, but refused to see her.
“His grandfather has insisted for 17 years that my son belongs to HIM and all his problems are a result of me, his mother,” she wrote. John Chakalos and his wife brought Nathan candy, The Wall Street Journal, and a radio, she wrote, and he would not come out of his room. She was desperate for her son to receive regimented treatment, she wrote.
“It would be inappropriate to make too much of normal family tensions about a difficult situation,” said attorney Dan Small, a partner at Holland & Knight, who is representing Linda Carman’s sisters. “Both Linda and her father loved Nathan and were worried about him, and occasionally had somewhat different views of how to help him. Sadly, eventually, neither approach worked.”
Linda Carman continued to care for Nathan after he was discharged. But one day when he was about 18, she came home to find him packing his bags, she later told a person close to her.
He was moving out, he told her: His grandfather had given him money, and he was using it to move into an apartment a few blocks away. Linda Carman told the person close to her, who shared the story with the Globe on condition of anonymity, that she was heartbroken.
Chakalos was a wealthy real estate developer who had served in the Army and married his high school sweetheart, Rita. The couple regularly donated to charity, and every Christmas they decked out a home they owned in New Hampshire in an extraordinary light display. They opened the display to the public and collected food pantry donations at the entrance.
Above all, Chakalos was dedicated to his family. “Without family, you’ve got nothing,” he often said, according to his obituary. He developed nursing homes and assisted living facilities throughout New England, and named some of the buildings after his children; less than three months before he died, he took Nathan Carman to the groundbreaking of Linda Manor.
“This was someone who was a product of the Depression, who grew up believing in family, hard work, and generosity and was a larger than life figure,” said Small. Chakalos’s wife died of cancer just a month before he did, after 59 years of marriage.
On Dec. 20, 2013, Chakalos’s body was found riddled with gunshots in his Windsor, Conn., home. Nathan Carman had had dinner with the 87-year-old the night before and was the last known person to see him alive, according to a police affidavit. Nathan Carman was supposed to meet his mother a few hours later, but never showed and did not answer his phone, the affidavit stated.
Nathan Carman discarded his computer’s hard drive and his GPS during the investigation that followed and failed to mention to police that he had recently purchased a gun with a caliber that matched the gun used to kill Chakalos, according to the affidavit. As police investigated, Carman’s relatives hired armed guards to protect them from him, the affidavit stated.
But Carman was never arrested, and the case remains unsolved. On Interstate 91 in Hartford, a billboard showing Chakalos’s smiling face offers a $250,000 reward for information. Chakalos left behind a $44 million estate.
About a year after Chakalos’s death, Nathan Carman moved to Vermont. Despite their distance, Linda Carman kept trying to strengthen her bond with her son, a close friend said.
Twice, they had gone on weeklong trips in the Canadian bush, dropped off by plane to fish Walleye and Northern pike, said a woman who works for the fishing trip company, based in Red Lake, Ontario. In 2013, they camped in a cabin on Cherrington Lake, and in 2015 they camped at Shearstone Lake, said the employee, who spoke on condition of anonymity.
On the second trip, she said, they capsized their canoe and had to float to shore. But that wasn’t an uncommon scenario, she said.
Last month, Nathan and Linda Carman set sail from a Rhode Island marina for an overnight fishing trip. Linda Carman told friends that they were headed to Block Island, about 20 miles offshore. Instead, Nathan Carman later told investigators, they went about 100 miles out.
The next day, Nathan Carman told investigators, he heard a “funny noise” in the engine of his boat, the Chicken Pox. The boat started to sink. When he turned to look, he said, his mother was gone.
Nathan Carman was found floating on a raft on Sept. 25. Officials are investigating whether he made modifications to his boat that potentially rendered it unsafe, according to a police affidavit.
Police have searched Nathan Carman’s home in Vermont and the Connecticut home where his mother lived with a friend, Monty Monterio, and his 3-year-old daughter. Monterio said Linda Carman was like a big sister to him, the kind of friend anyone would be lucky to have. She let him move into her home after his divorce eight months ago, he said, when he had nowhere to go.
During the search of Linda Carman’s home, officers confiscated her computer, documents, and three large jars filled with her handwritten notes, Monterio said.
She filled the first jar with notes about what made her happy, Monterio said, and the second with notes about things she wished would get better. The third jar, he said, was for the problems she was leaving up to God.