Every Town - A Grandfather Shot, A Mother Lost at Sea — All Eyes on Nathan Carman

Episode Date: June 13, 2025

Is This the Most Twisted Family Mystery in New England? The Mysterious Deaths Surrounding Nathan Carman. 👀 Watch This Episode On Youtube: ⁠https://youtu.be/0HSCi9-ASaM 👁 Check out our movie... AN ANGRY BOY for FREE! ⁠https://www.youtube.com/watch?v=BvtlOlODQ8g&t=5238s⁠ ⁠https://tubitv.com/movies/100029672/an-angry-boy⁠ International & Other Ways To Watch: ⁠https://www.anangryboy.com/⁠ 💀 MERCH: ⁠https://scary-mysteries.teemill.com/⁠ 💀 Free 7 Day Trail on Exclusive Episodes, Podcasts & Perks! ⁠https://www.patreon.com/scarymysteries⁠   🎧 Our Other Podcast Scary Mysteries: ⁠https://open.spotify.com/show/3ZooEZMoZ421WdsOVJhVkT⁠ 👁 X: ⁠https://x.com/ScaryMysteries1⁠ 👁Instagram: ⁠https://www.instagram.com/andrew.fitzg⁠ 👁 TikTok: ⁠https://www.tiktok.com/@andrewfitzgerald⁠ 👁Facebook: ⁠https://www.facebook.com/scarymysteriesofficial⁠ 👁 X: ⁠https://x.com/ScaryMysteries1⁠   🗣 Business Inquiries, questions and comments hit us up at ⁠scarymysteries1@gmail.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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Starting point is 00:00:00 Are you ready to dive into the unknown? Join me, Peyton Moreland, on Into the Dark, the true crime podcast from Ono Media with a hint of horror and mystery. Each week, I dive into a different case, breaking down the facts, and pondering the age-old question, why do people do what they do? Now, sometimes the answer isn't so clear, and that's why I'll also explore conspiracy theories, hauntings, and all things spooky. From the Green River Killer to the Mothman incident, we will unravel all of the questions that keep us up at night. So don't miss out. Subscribe now on your favorite podcast platform.
Starting point is 00:00:40 New episodes drop every Wednesday. Into the dark, where true crime meets the eerie unknown. Every town has a dark side. Nathan Carmen, who is from Middletown, was charged with killing his mother after a boat ride in 2016, left her missing at sea. Nathan Carmen, the man whose grandfather and mother, died in separate, suspicious incidents, appeared in court today to try to collect his inheritance. He used to murdering his mother at sea six years ago, says he didn't do it. Today, Nathan Carmen was in federal court.
Starting point is 00:01:23 Nathan Carmen charged with killing his own mother during a boat trip in 2016. On the open ocean, with nothing but sky and water as far as the eyes can see, well, somewhere out there, a young man is found drifting alone on a life raft. He has no food or water. It's just him, but his story doesn't quite add up. This was 2016 off the coast of New England, and 22-year-old Nathan Carman had just been quote-unquote rescued after claiming his fishing boat sank during a trip out there with his mom.
Starting point is 00:01:56 She was gone, vanished beneath the waves, and he somehow survived. At first glance, it looked like a tragic accident, but he dig a little deeper. You'll find a rabbit hole here of shady details, family fortune, and a very suspicious past. Because this wasn't the first time someone close to Nathan had died under mysterious circumstances. When investigators started pulling at the threads, what they unravel was a tale of greed, betrayal, and calculated manipulation that had spanned years and involved not just one disappearance, but a murder as well. Hey guys, it's Andrew, and thanks for tuning in to an
Starting point is 00:02:40 another episode of Every Town where today, we're headed up to the quiet suburbs of Connecticut and the stormy waters off Rhode Island to take a deep dive into the strange story of Nathan. A young man at the center of a mystery that's still raising eyebrows to this day. Was he just unlucky, or was there something much darker at play here? This is the twisted mystery of Nathan Carman. On December 19th at 2013, at a Greek restaurant on the Burles, Turnpike in Newington, Connecticut, John Chackelos, an 87-year-old real estate developer worth nearly $50 million, finishes a nice dinner with his grandson Nathan.
Starting point is 00:03:35 And they climb into Nathan's Nissan Titan pickup truck. The snow is all but melted, and the night is clear, and conservative talk radio fills the cab as they discuss their mutual disdain for Hillary Clinton. Just a grandfather and a grandson, ending in ordinary evening. Or so it seems. By 8.30 p.m., they pull in to Chekalo's driveway on Overlook Drive in Windsor, and Nathan helps his grandfather get inside the house, and they spend a few minutes talking. The phone rings, and it's Chuckalow's much younger lover returning his call from earlier that day when he had tried reaching her from an erotic boutique in Hartford.
Starting point is 00:04:20 The conversation then starts to take a flirty turn, and the older millionaire, not wanting to end it just yet, casually walks Nathan to the door with a smile. He whispers into the phone. Nathan's just leaving. Give me a minute. I want to say goodbye to my grandson. They hug. The door closes, and John returns to his phone call, making plans for a romantic getaway to New York City with his new toys from the love boutique. But that trip is never going to happen, because unfortunately for John, while this is the last time anyone will see him alive again. And the next morning arrives like any other. It's December 20th, and Elaine Chekaloz is making her regular drive to her father's house for breakfast.
Starting point is 00:05:11 As a registered nurse, she always checks that he's taking his heart meds, the ones that he keeps on the right side of the kitchen sink. As she pulls into the driveway at 8.15 a.m. and parks next to his car. Nothing seems out of place. She lets herself in as usual and calls out his name. but something's off and the house is very eerily quiet. You see, John has been an early riser since his army days back in the 40s. By this time, he'd normally be at his desk, shuffling papers,
Starting point is 00:05:46 the smell of fresh coffee filling the house. But today, that office is empty, and the desk is untouched. Elaine's heart begins to raise as she goes through the list of what-ifs. And what if he fell out of bed? and what if he died in his sleep? She knows that something has happened, so she moves toward his bedroom, each step heavier than the last.
Starting point is 00:06:11 The door creaks open, letting in a sliver of light from the hallway. That's when she sees him. And still lying on the king-sized bed, his sheets and comforter are soaked in red. Half his head is completely gone. She lets out a terrified scream and stumbles outside with trembling fingers, dials 9-1-1-1.
Starting point is 00:06:32 Within minutes, the quiet neighborhood transforms into a full-on crime scene. Police cars line the street. Officers moved back and forth across the snow-covered lawn. Inside the house, well, that's where investigators discover something that immediately tells them some valuable information about why this man is now dead. You see, John always kept stacks of cash on hand. Old school emergency money, he called it. And all of that was untouched.
Starting point is 00:07:04 and the valuables in the home all still there too Lieutenant Christopher McKee walks through the house taking it all in and he now knows this wasn't a robbery turned violent and all signs point to the fact that this was personal money was clearly not a motive at least not that money the killer it appeared walked in and stood at the foot of the bed
Starting point is 00:07:30 while Chigolo slept and then fired multiple shots from a rifle one entering the stomach and two hitting his head. The ballistics team examines the bullet fragments and makes their determination. The murder weapon was most likely a Sig Sauer rifle. Now here's where our story takes a real dark turn. As detectives begin interviewing family members, one name keeps coming up over and over again.
Starting point is 00:08:13 Nathan Carman, the victim's 19-year-old grandson, and here's why. Nathan wasn't like most kids, you see. Growing up in Connecticut, the son of divorced parents, Linda and Clark, he struggled with Asperger's syndrome. Carmen was treated for mental health issues from the time he was a small child until he was 17 years old. Since that time, Carmen has avoided any mental health treatment. So he lived a pretty lonely existence overall.
Starting point is 00:08:43 But John Chaccolos, he saw something different in Nathan. And Chacchalos had four daughters and eight. grandchildren, but Nathan, he was special. He was the first male grandson, and in Chickalose's eyes, that meant everything. The old man doaded on him, paying for his education, his housing, even buying him a horse. While other family members fought for scraps of attention and money, while Nathan got it all, the affection, the gifts, and the inheritance. And this created poison within the family. All this special treatment built some deep resentment. as you can imagine.
Starting point is 00:09:25 Checolos's daughters and grandchildren were there, watching Nathan get showered with everything they were desperately competing for. True crime author Casey Sherman would later describe it as Shakespearean, like King Lear, pitting his children against each other. Except this wasn't fiction. This was a real family being torn apart by $50 million. That's how much was up for grabs if and when John came to pass. and Nathan, always getting the attention from him, stood to get most of the inheritance,
Starting point is 00:09:58 and he knew that. So, right there was your motive. And police sat down with Nathan, and they started with a simple question, do you own any guns? Nathan's answer was just an air gun. But here's the thing about that. It was a lie. And the cops knew it going in. And they knew that just weeks before his grandfather's murder, Nathan had traveled up to New Hampshire.
Starting point is 00:10:26 Hampshire, the good old live-free or die state where he purchased a sig-sour rifle, the exact type of weapon used in the killing. When confronted with this fact, Nathan changes his story. Yes, he admits he did buy the rifle, but he lost it. He explains that he bought it because he didn't feel safe at home, but the gun is never found. And then there's Nathan's alibi, or rather the hole in it. Nathan tells police he left his house around 3 a.m. on the night in question to meet his mother for one of their fishing trips. But on the way, he claims he got lost. Now remember, this is someone who lived in this area's whole life.
Starting point is 00:11:10 And somehow, during the exact hour his grandfather was murdered, Nathan goes completely off the grid. He's not heard from until 401 a.m. To one missing hour, one missing gun, and one dead millionaire. Investigators obtained a search warrant for Nathan's apartment in July of 2014. and they find a Remington tactical shotgun, ammunition, and something else. Notes containing intricate details about sniper rifles and improvised explosive devices. One neighbor at the time tells police that Nathan is a time bomb waiting to go on.
Starting point is 00:11:49 They also discover that Nathan destroyed his computer's hard drive and discarded his car GPS unit around the time of the murder. And when pressed, Nathan invokes his Fifth Amendment rights and stops talking altogether. He knows the evidence is mounting, and then the police draft an arrest warrant. They plan how to take Nathan into custody without endangering anyone else,
Starting point is 00:12:13 because at this point, they believe he's already killed once and owns multiple firearms. But just when they're ready to move, the warrant comes back unsigned. The prosecutor wants more evidence. And tries they might, they just can't get it.
Starting point is 00:12:31 And so then, this case goes cold. And three years passed by and Nathan is rich. He got some of that inheritance, which he uses to buy a house in Vermont and a fishing boat, and he names the chicken pox. And he could have just gone quietly into the night, lived a life that kept the spotlight off of himself.
Starting point is 00:13:00 But do you really think that's what Nathan did? His relationship with extended family had deteriorated completely by this point. At the funeral of his grandfather, Joy Washburn, a caretaker of Chocalo's New Hampshire estate, claims Nathan's Aunt Valerie approached her saying, Nathan killed my father. He'll never be prosecuted. If anything, they'll place him in a mental institution. And now we arrived to September 17th of 2016,
Starting point is 00:13:32 and another chapter in this family's dark saga is about to unfold. Nathan invites his mother, Linda, on yet another one of their fishermen. trips. But let me tell you something about Linda Carmen that you'll find interesting. She doesn't like fishing at all. She doesn't eat fish and she's actually nervous about water in general. But she goes fishing with Nathan regularly because he likes it. And as a mother she's trying to nurture their relationship. It seems like a good idea on paper, but in reality, at least with Nathan, maybe it wasn't such a good idea. The day of the trip started out at Ram Point Marina in Rhode Island. Fellow boater, Mike Ayazi, watches Nathan work on his aluminum boat for hours.
Starting point is 00:14:28 But he notices Nathan isn't fixing things. He's drilling holes. And pretty big ones, too, some as large as a half a dollar. He's removing screws from the trim tabs, you know, the things that keep boat stable. Iosie, who drills holes for a living, warns Nathan that if he does that, without those the boat could say. And Nathan brushes him off saying trimmed tabs aren't necessary, which doesn't make a whole lot of sense. Iosie then asks about his plans for the day, and Nathan says that they're going to block Canyon, 75 miles offshore to catch some fish. That's when Iosie notices there are no fishing poles in the boat,
Starting point is 00:15:11 so pretty odd. When Linda gets the dock, she sends a quick text to three, friends, letting them know she's heading out towards Striper Rock, southeast of the windmills, and plans to be back by 9 a.m. And she tells them to call her at noon if they haven't heard from her. It's something she always does. She even includes a photo of the boat's registration number, just to be extra cautious. Security cameras capture them preparing to board around 11 p.m. And as they depart into the darkness, Linda texts her friends one last time saying,
Starting point is 00:15:51 just leaving the dock, and these will be her final messages. Within an hour, a fisherman spots the chicken pox, heading south past Block Island. He does a double take, and the cabin lights look odd, too close together. The seas are calm, and the boat's moving slowly, and that's the last sighting of them out in those waters. The next day, Linda's friend Sharon Hartstein expects that call by noon. When it doesn't come, she grows content. concerned. By that evening, they contact the Coast Guard, triggering a huge search and rescue operation. From Boston, search and rescue controller Richard Arsenal developed search models.
Starting point is 00:16:39 Using Linda's cellular data, they identify her phone's last location at 1245 a.m. on Block Island's south side. They deploy helicopters, boats, and map out 1,282 square nautical miles. After searching, a huge area, they turn up with nothing at all. No boat, debris, or signs of life. But back on land, investigators discover something bizarre at the marina. They locate Nathan's car and inside is a bucket of eels, the bait that they plan to use. If they left the bait behind, though, what were they using to fish with? The FBI also found that Nathan recently bought an anchor that would never work for his boat,
Starting point is 00:17:38 along with lanes of chain. He also destroyed his computer before this trip. When Coast Guard investigator Eric Gemp learns about the missing boat, something doesn't sit right. With perfect weather conditions and the Coast Guard success rate, how could they find nothing? It's almost as if the boat had deliberately disappeared. And the search continues for seven days,
Starting point is 00:18:07 and in that time local fishermen find floating debris, a marine deck box cover, a pillowcase, empty cooling containers, but nothing really connects to the chickenpox. The Coast Guard contacts Linda's next of kin and gets an education and family dysfunction. Instead of showing concern, Nathan's Aunt Valerie launches into accusations against the young man, calling him the town freak and claiming he murdered their father. She says his pattern is just continuing and that Nathan has, every reason to kill Linda. She's about to inherit their father's New Hampshire mansion
Starting point is 00:18:47 in a probate settlement scheduled for the following week. But if Linda dies, then that goes to Nathan. But what Valerie doesn't know in that moment is that Linda has already cut Nathan from her will. The reason being that she herself clearly thinks her own son likely murdered her father. This would also help explain the super precautions she took before heading out on that fishing trip. though it doesn't appear like it was enough to save her. By September 24th, after more than a week of searching, the Coast Guard officially called off the mission. Commander Arsenal and his team are left unsettled,
Starting point is 00:19:31 and there's no debris, no oil slick, nothing. Despite the massive operation, it's as if the sea swallowed everything without a trace. But then, the very next day on September 25th, A Chinese cargo ship called Orient Lucky spots an orange ball bobbing in the waves 100 miles off the coast of Martha's Vineyard. They realize it's a life raft, and it has someone inside of it. Nathan emerges and swims towards the freighter as they toss him a life rink, but there's no Linda. Coast Guard officials are stunned by Nathan's condition. After supposedly spending seven days at sea, he shows none of the expected symptoms.
Starting point is 00:20:20 His lips aren't even cracked. He's not dehydrated. He answers questions calmly and directly, as if he had spent a week on a cruise ship rather than fighting for survival. But that's not the only thing weird here. His location makes no sense either. Ocean current should have pushed him west. Instead, he's found 35 miles east, contradicting every drift model available.
Starting point is 00:20:48 So, what's Nathan got to say? about all this. I would just like to thank the public for their prayers and for their concern for both my mother and for myself. I feel healthy. I feel healthy. Emotionally, I've been through a huge amount. Well, according to him, they spent about an hour fishing near Block Island.
Starting point is 00:21:13 Then around 1 a.m., he convinced Linda to push further out towards Block Canyon to try for tuna. She was hesitant, worried about safety and missing work, but Nathan says he talked her into it. As the sun started a rise over the horizon, he claimed the boat suddenly had engine trouble, and water began pouring in fast. He told his mother to reel in the lines while he grabbed the survival gear, and then without warning, the boat just gave out beneath them. One moment it was there, and next it was gone.
Starting point is 00:21:50 Nathan says he ended up in the water clinging to the safety equipment. He managed to swim to the life raft, but he never saw his mother again. For seven days then, Nathan says he survived on water packets and emergency rations. And he feared starvation or capsizing in 13-foot waves. Yet the smoke flares in a survival kit never used. While investigators kept digging, Nathan wasted no time filing an $85,000 insurance claim for the lost boat. But the insurance companies weren't buying the story. and they denied the claim, pointing to holes in his story and literal holes in the boat that he had made himself under the guise of fixing it.
Starting point is 00:22:49 A judge later ruled that Nathan had made poor repairs to the boat, but couldn't say for sure whether he had deliberately sunk it. As the case dragged on media coverage shifted the narrative, Nathan went from being seen as a tragic survivor to a possible killer of two family members. The years ticked by debating that. And then finally on May 10th of 2022, a major development. Nathan was officially indicted for his mother's murder. The nine-page indictment states that Nathan Carmen killed his grandfather in 2013, then his mother in 2016. And it says he did it to get insurance and family money.
Starting point is 00:23:30 The unsealed indictment states Nathan Carmen shot his grandfather, John Chocaloz, while he was sleeping. The indictment also says Carmen got rid of his hard drive and lied to investigators, then collected more than $500,000 after his death. If and when this gentleman killed his grandfather, he may have done so for the benefit of himself, thinking that he was going to be the beneficiary of a large inheritance. The case that had long simmered in the background, as they tried to piece together exactly what Nathan did during those seven days at sea,
Starting point is 00:24:03 was starting to boil over. No matter how you cut it up, whatever the real story was, there were just too many inconsistencies with Nathan's timeline, too many puzzle pieces that didn't fit. The repairs to the boat, the fish in his car, being cut out of his mom's will, the death of his grandfather, the fact that he looked pristine when he was rescued. As he entered court, he yelled not guilty, and then once again inside in a much more solemn tone, Carmen again pled not guilty to all charges, including murdering his mother. As the trial date approached, the anticipation grew,
Starting point is 00:24:43 and for some it was a long-awaited moment of justice, for others, a painful reminder of everything that had been lost. But the trial never came. Even though Nathan never said he was guilty, it would appear like he had a very guilty conscience. On the morning of June 15th of 2023, the cell door is open for breakfast, but Nathan didn't come out of his. And he was found dead in his jail.
Starting point is 00:25:13 cell. You're taking the cowards way out of the whole situation. Nathan Carmen's lawyers were blindsided by their client's death. The 29-year-old found dead alone in his cell overnight. I spoke with him last night for an hour. He was in fine spirits. We were very encouraged. We had action items that we were going to address today. His lawyers, though, say there was a note found in his cell. They still don't know what it says, but it may provide clues into his death. Carmen was just months away from standing trial, for the murder of his mother. He's accused of killing her on a fishing trip off the coast of Rhode Island in 2016, all to inherit millions of dollars. And just like that, the case collapsed. The murder charges
Starting point is 00:25:56 were dismissed and the cloud of uncertainty thickened once again. Yet the story wasn't over. And best-selling true crime author Casey Sherman has investigated this case through and through, and in great detail, has recently released a book about his story. findings called Blood in the Water. And what he uncovered showed another side of this whole thing, when authorities almost quietly tucked away. He found a lead in Joy Washburn, a woman the FBI considered incredibly credible,
Starting point is 00:26:31 who revealed that just two weeks before John Chikolos was killed, a family associate had approached her with an offer of $10,000 to kill him and make it look like a hunting accident. And that wasn't all. Sherman also came across a text message from Linda, sent during a tense family dispute when her father demanded that relatives repay 30 million from a family trust that had been chipped away at. Linda's response was essentially to blow her father's head off and be rid of him. And so was Nathan Carmen then the only person to blame in all this? It doesn't necessarily appear to be.
Starting point is 00:27:16 As Sherman says that based on what he's uncovered, if he were or, on the jury in Nathan's trial, he would have voted to acquit. In his view, Nathan loved only two people in the world, his grandfather and his mother. And yet, he stood accused of murdering both for a fortune he would have inherited regardless. So were others in the family a part of this whole plan using Nathan's disabilities to their advantage? And was he a cold-blooded killer, or maybe a mix of both, a victim of wealth and severe family dysfunction? And the aunts who once accused him showed up at Nathan's funeral. They buried him beside the grandfather whom they believed he had killed.
Starting point is 00:28:07 In the end, they said Nathan was a deeply troubled soul, one who needed peace. The $50 million fortune is still tied up in probate currently. Linda's body was never found, and whatever truth Nathan held onto, well, he took that with him. The waters off-block Island still hold their secrets. And some stories just don't want to be solved. And this looks like one of them. What really happened that night at sea? Who killed John Chikolos?
Starting point is 00:28:40 And if it wasn't Nathan, then who? And the truth, just like Linda Carmen, remains lost at sea. So that's going to do it for this week's episode of Everytown. I hope you all enjoyed it. If you did, please do me a solid before going to the next episode and rate and review our podcast. I just got word 95% of our regular listeners have not, and it would really help us out. Appreciate it very much.
Starting point is 00:29:15 Thank you for tuning in. And remember to come on back next week for another episode filled with scary, strange, and mysterious stories. Because you never know. Maybe your town will be next.

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