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Late Nights with Nexpo

The Billion Dollar Mystery

Wed, 05 Mar 2025

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A powerful couple, a gruesome discovery, and a mystery worth billions. Who killed Barry and Honey Sherman – and how did they get away with it?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Chapter 1: What happened at the Sherman mansion on December 13th, 2017?

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It's December in Toronto. It's snowing tonight. A 12,000 square foot mansion stands dark. None of its windows are illuminated, not even the basement office. That's unusual. This is the home of billionaire power couple Barry and Honey Sherman, owing to the wild success of his generic pharmaceutical company, Apotex. Barry is both a workaholic and an insomniac.

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He does his best thinking at nighttime, and his employees are used to receiving emails and calls from Barry at all hours. But on this night, the night of Wednesday, December 13th, 2017, his employees received no late night messages from Barry at all. In fact, it's the first time they recall this ever happening.

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What the employees don't yet realize, though, is that they'll never receive a message from Barry Sherman ever again. And it's because deep within the bowels of the Sherman mansion, something gruesome is happening, and it'll haunt investigators and the community for years to come. Two days later, the sun rises on the Sherman's upscale neighborhood. It's no longer snowing.

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It's the morning of Friday, December 15th, 2017. There's a for-sale sign in the front of the Sherman's home, and it's been there for weeks. The Sherman's realtor is scheduled to show their home to potential buyers at around 11 o'clock, but the Sherman's housekeeper, who arrives every Friday, is the very first to arrive at 8.30 a.m.

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Immediately upon arrival, though, a few things strike her as slightly unusual. First, the morning newspaper is still lying on the ground out front. It hasn't been taken inside. This only happens when the Shermans are out of town, but the housekeeper can plainly see that the Shermans are home.

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Honey Sherman's Lexus is parked in the circular driveway, still dusted in snow from the storm Wednesday night. The side entrance most commonly used to enter the home is locked, second unusual thing. Even so, she knocks, expecting Honey or Barry to come let her in. However, no one comes to the door. Finally, she lets herself in with her key and goes to disarm the home security system.

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But surprisingly, there's no need to. It's disabled. This housekeeper has worked for the Shermans for three years, and this is the very first time she's ever seen the alarm system completely off. Something is wrong. The housekeeper can sense it. But she has a job to do, so she begins moving from room to room, cleaning and tidying as she goes and dreading what she might find around the next corner.

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The bed in the master bedroom is already made, but Honey always leaves the bed unmade on Friday mornings for housekeeping to handle. In Honey's bathroom, the sink is dry, implying that Honey didn't go through her morning ritual at her mirror. A thought occurs to the housekeeper. She remembers that Barry and Honey were planning a Florida vacation.

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Perhaps those plans had changed and they simply left earlier than planned. Maybe as soon as it began snowing on Wednesday, the couple impulsively decided to bolt for warmer weather and overlooked a few things as they rushed out the door. The housekeeper reassures herself that this is what happened and continues her work.

Chapter 2: How were Barry and Honey Sherman discovered?

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Shortly before 11 a.m., the Sherman's realtor comes into the home with a pair of interested buyers. And to start, their tour begins on the upper floors. Oddly, they find Honey's iPhone lying on the floor of a small powder room near the front of the house. But otherwise, the house is tidy and the showing goes well. The buyers, at first, seem interested. But then it's time to show the basement.

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The realtor has shown the house enough times to know that the basement portion of this tour is where buyers always get cold feet. So as they descend the stairs, the realtor braces herself for the worst. The problem with the basement is that it makes people uncomfortable. It's almost completely devoid of color or decor. It's just beige and gray surfaces everywhere.

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But there is one room in the basement that has decor. And that's the hobby room. In the corner of it, two life-sized human statues sit on large speakers, with their legs and arms positioned in an attempt at being casual. The statues are so-called junk sculptures, constructed entirely of brightly colored trash. They do stand out in the otherwise drab space, but not in a good way.

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There's no other way to put it, the statues are creepy. So when the tour group reaches the bottom of the staircase, the realtor rushes them past the hobby room and towards one that they think will make a better first impression, the indoor pool room. This massive room is dark when they arrive. The realtor flips on the overhead lights and immediately there's a gasp from someone in the group.

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A moment later, the realtor sees why. Barry and Honey Sherman are in the room with them, across the way by the far edge of the pool. From this distance, the realtor can't tell what they're doing. It looks as though they might be doing yoga, but whatever they're up to, it's strange that they're doing it in a completely dark room.

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The realtor quickly ushers the clients from the room and mentions the scene to a gardener working on the property. In response, the gardener offers to go see what's up. The gardener enters the pool room and walks up to the Shermans. However, upon closer inspection, it becomes clear that the Shermans are not doing yoga at all. Barry is in his work clothes, and Honey in her everyday attire.

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Their legs and arms are positioned in an almost casual manner. They almost look like they're politely seated in a waiting room, except their posture is too unnatural. They're both reclined too far back, and it looks uncomfortable, if not impossible. Now right on top of them, the gardener can see exactly why Barry and Honey seem so uncomfortable.

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Two leather belts, one around each of their necks, are tied tight like nooses, tethering them to one of the pool's low metal railings so that they're left dangling in their strange, half-sitting positions.

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In no time at all, the realtor is on the phone with 911, frantically trying to explain the grotesque scene to the dispatcher, trying to explain that Barry and Honey Sherman are dead, murdered right inside their own mansion. One week later, the Toronto Police Department is settling into their investigation, but the case is making international headlines now and the public wants answers.

Chapter 3: What is the police's initial theory on the Sherman case?

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As a result, Honey never went down there if she could help it. Two days after the bodies are found, police announce that, according to autopsies, Barry and Honey both had the same cause of death, ligature neck compression, aka strangulation with a rope or constricting band.

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The preliminary autopsy report for Barry notes that the fragile, U-shaped hyoid bone in his neck is still intact, unbroken, which is odd because typically, deaths involving strangulation break it. Because of this, investigators see this as an indication that this case was not a double homicide, but rather a murder-suicide, in which Barry Sherman killed his wife, then took his own.

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Self-strangulation is an extremely difficult way to kill oneself. Remember, Barry did not hang himself. His feet were touching the floor, meaning that he could have reflexively stood up at any time once he became desperate for oxygen. This is why ligature neck compression is such a rare way for one to commit suicide, yet it's not completely unheard of.

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Police investigators are intrigued by the murder-suicide theory because it fits with so much of the evidence they've gathered. If Barry Sherman is their killer, it would explain why there was no sign of forced entry, why the home security system never went off, and why no unexpected DNA or fingerprints were found in the house.

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And also, if Barry attacked Honey, it would explain why Honey's face showed signs of violence, while his didn't. On top of everything, though, another reason the police are pursuing this theory so aggressively is because of its potential motive. Barry and Honey's 40-year marriage, as it turns out, was secretly on the rocks.

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According to those who knew the Shermans well, Honey and Barry were a completely different couple in private than they were in public. Outside their home, Barry and Honey presented themselves as a happily married couple, constantly attending fundraisers and events on each other's arm. But within the privacy of their own home, Honey and Barry reportedly kept their distance.

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There were rumors that they'd begin sleeping in separate beds, and that Barry spent nearly all of his time at home, working in his basement office. These rumors were bolstered by emails and text messages obtained by police. Honey seemed frustrated with Barry's workaholic tendencies, while in return, he accused her of being quote, abusive to him and their children for years.

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And so, the Toronto police quietly adopt the idea that Barry Sherman killed Honey and then himself as their working theory, proceeding to investigate this as a murder-suicide. But police aren't quite ready to present their working theory to the press, as there are still some pieces of evidence that don't quite fit with the murder-suicide narrative.

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And investigators know they'll need to get them cleared up before they publicly accuse the legendary businessman and philanthropist Barry Sherman of something so heinous. That's the plan anyway, but it doesn't quite work out that way. Instead, the investigator's working theory gets leaked almost immediately, leading to all hell to break loose. The funeral is massive.

Chapter 4: Why do the Sherman children disagree with the murder-suicide theory?

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So with this in mind, to Jonathan and his siblings, the police's murder-suicide theory feels improbable, irresponsible even. In their eyes, not only are the police wrong, but their theory is also destroying a great man's legacy in the process. No matter how you look at it, a targeted double homicide simply cannot be ruled out.

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Barry had too many powerful enemies and bitter business rivals who lost against him in court. And besides, who on earth commits suicide by ligature neck strangulation? It's outlandish. If they were a family of average means, Jonathan and his siblings might have had no choice but to quietly sit by and let the Toronto PD's investigation run its course. But Jonathan and his siblings are billionaires.

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They have the means to hire a completely independent team of experts and private investigators. They have the means to fund their own investigation, one that'll bring the truth to light and restore their father's good name. Jonathan and his siblings act quickly. They hire criminal defense lawyer Brian Greenspan to lead a private, parallel investigation into their parents' deaths.

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Greenspan's first order of business is to arrange a second set of autopsies. For this, he taps Dr. David Chason, a veteran forensic pathologist with an excellent reputation. Greenspan knows that it's crucial that his investigation is done by the book and in the light of day.

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And so he invites everyone who was present at the initial autopsies to attend the second autopsies, including a number of Toronto police officers and detectives assigned the Sherman case. Oddly, though, every single one of them declines. The Toronto PD, it seems, doesn't appreciate having their work picked over. Even so, however, there is one person who accepts Greenspan's invitation.

1306.327 - 1332.196 Narrator

Dr. Michael Pickup, the young staff pathologist who performed the initial autopsies of Barry and Honey Sherman. To Greenspan's surprise, Dr. Pickup takes no offense to having his work double-checked. Rather, he's eager to help. Pickup explains that he delivered his preliminary report days after the Sherman's bodies were found, but the official autopsy report would take about a month to complete.

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So the preliminary report was precisely that, preliminary. The only conclusion Dr. Pickup reached in this preliminary report was the medical cause of death, ligature neck compression for both Barry and Honey. But what this preliminary report didn't reach any conclusions about was the manner of death.

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The manner of death refers to the circumstances surrounding a death, whether it was natural or intentional, suicide or homicide, etc. And in this section of his preliminary report, Dr. Pickup merely listed out the three possible options, murder-suicide, double homicide, and double suicide, with the intention of narrowing the list down in his final report.

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And so, on December 20th, Dr. Chaison carries out the second set of autopsies with Dr. Pickup and Greenspan's small team of private investigators in attendance. With this, Dr. Pickup proves to be invaluable. He tanks Dr. Chaison through his thought process and the incisions he made in his initial autopsies.

Chapter 5: What was Barry Sherman's business strategy with Apotex?

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But no garrote or thin rope was found anywhere in the house, so the idea that Barry could have killed himself was out of the question. Barry couldn't have strangled himself, then gotten rid of the garrote afterwards. It's simply impossible. On top of this, there were thin markings on both Barry and Honey's wrists, indicating that their hands were bound at some point, possibly with zip ties.

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Once again, nothing of the sort was found anywhere in the house, implying that whoever bound them took that evidence with them when they left. Dr. Chaison's report also addresses the matter of Barry's intact hyoid bone. Chaison, who happens to have researched this exact topic extensively, points out that the hyoid bone doesn't always break during strangulation.

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His report also re-emphasizes a key fact that may have been overlooked in Dr. Pickup's preliminary report. That Barry's isn't the only hyoid bone that's intact. Honey's is fully intact, too. Likewise, Greenspan's team makes sure the press hears about certain pieces of crime scene evidence that haven't been properly emphasized by the Toronto Police.

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Like the fact that an exterior door leading to the basement was found unlocked at the crime scene, and that one of the home's windows was found ajar. The fact that there was no sign of forced entry doesn't necessarily make Barry Sherman the killer, as the Shermans lived in an extremely upscale and safe neighborhood, and they were evidently a bit lax about home security.

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For all they knew, their killer could have simply walked inside that evening, completely undetected. Greenspan's team also discovers that Toronto Police failed to collect all of the fingerprints and potential DNA at the scene, and their private team discovers at least 25 new palm or fingerprints that the police missed.

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In light of all of this new information, Greenspan's team asserts that Toronto Police are headed down the wrong path, and that perhaps Barry and Honey were actually the victims of a targeted double homicide. The private investigation's findings begin to turn the tide, just as Jonathan and his siblings had hoped it would. And now, the pressure is on the Toronto Police to respond.

1610.742 - 1633.967 Narrator

A week later, the Toronto PD calls a press conference. They walk back their murder-suicide theory and announce that they're now investigating the Sherman's deaths as a targeted double homicide. With this, Jonathan and his siblings are relieved, but not satisfied. Their father's reputation might be saved, but justice has not been served.

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And so, they announce a $10 million reward to anyone with info leading to the arrest of their parents' killer, and wait to see what comes of it. But what about Honey Sherman? Why was she killed? If her husband was targeted by a business rival or something along those lines, then why did Honey become wrapped up in all of it?

1661.126 - 1680.298 Narrator

If a lifelong killer really did gain access to the home through their basement, the very basement where Barry was most certainly working, then why did they go upstairs in search of Honey? It's not like Honey could have accidentally stumbled in on a murder in progress in her basement. Her knees were far too weak to even come down the stairs.

Chapter 6: How are the Sherman children challenging the police investigation?

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But out of nowhere, in 2019, security camera footage that supposedly never existed begins to surface. While it's true that the Shermans had no security cameras on their own property, one of their neighbors did. Because of the way the neighbor's cameras were positioned, they captured footage of the street in front of the Sherman's home. And on the night of the murders, these cameras were running.

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No, this footage was available to Toronto police officers from day one of their investigation. On the morning of December 5th, 2017, when police first taped off the crime scene at the Sherman's home, the neighbor walked over and told a Toronto police officer about his cameras. But because the Toronto PD believed the case to be a murder-suicide, they dragged their heels.

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The neighbor actually had to remind the police about the footage on four separate occasions before they finally came to retrieve it days later. But even then, they still didn't review it right away, and the footage became lost in the shuffle.

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But in 2019, and now that the case is being investigated as a double homicide by both the Toronto PD and Greenspan's private investigation, this footage gets dug up and finally receives the attention it deserves. and let me tell you, it definitely deserved it.

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According to investigators who have seen this footage, the most shocking portion takes place on the morning of December 14th, just hours after the Shermans were likely killed and a day before their bodies were discovered. A man parks his four-door sedan on the street in front of their home, and the car remains there for over an hour.

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During this time, a man takes three separate trips into the Sherman's home. And not just to the front porch, he physically goes inside their home three separate times. This unidentified man spends a total of 29 minutes inside the mansion, his facial features and the car's license plate too grainy to make out. But it's a shocking revelation. Could this man have been involved in their murders?

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Did he clean up or otherwise tamper with forensic evidence while inside? Was he the one who staged the bodies in their bizarrely casual cross-legged positions? If the police have any answers, they sure remain tight-lipped. But even stranger, as it turns out, this is not the only camera footage the police have been sitting on.

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In 2021, on the four-year anniversary of Barry and Honey's deaths, the Toronto PD released a second clip of security camera footage that has left them equally baffled. It comes from a different home in the area, located 1.3 kilometers away from the Sherman home. In this 22nd clip, an unidentified man is seen walking in the direction of their home.

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During the time window, police believe Barry and Honey were killed. And after poring through 2,000 hours of security camera footage taken from the area that night, this unidentified man is the only individual whose presence in the area police can't explain. It's unclear whether it's the same man who parked his sedan on the street on December 14th.

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