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- [00:00]
Podcast Host/Announcer
Welcome to Canadian True Crime, a completely independent project funded mainly through advertising. To listen ad free and early, subscribe to our premium feed on Amazon Music. Included with Prime, Apple Podcasts and Patreon, this podcast often has disturbing content and course language. It's not for everyone. Please take care when listening.
- [00:21]
Kristy Lee
Hi there, it's Kristy Lee. I hope you're well and thanks so much for tuning in after a longer than expected delay. I appreciate it. Before we begin, an important legal note about why I chose this case. Every time controversial Canadian businessman and TV personality Kevin o' Leary pops up in the news, which is often because Mr. Wonderful loves the spotlight, the comments sections fill with references to a 2019 boat collision that caused the deaths of two people. Kevin O' Leary built his empire on bluntness and playing a reality TV supervillain
- [01:02]
Kevin O'Leary
for three years. Robert, you could see it in that.
- [01:04]
Kristy Lee
So what?
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Kevin O'Leary
This is business. Life is hard. Then you die. Get over it. Well, maybe in your world this sounds terrible, but unfortunately I have the track record to be this arrogant. It's awful. I hate me. Okay, that's wonderful, but how do I make money off depressed people? You know, this is all crap. Money and tears don't mix. Get over it. Life's hard. Money doesn't care. Your tears don't add any value.
- [01:34]
Kristy Lee
He was already rich, but his on screen Persona made him famous. It also meant that when tragedy struck and he was involved, the public at large were hard pressed to give Kevin o' Leary the benefit of the doubt. He was never charged and his wife, Linda O' Leary was found not guilty at her 2021 trial. But five years later, the conspiracy theories around this case have persisted and that intrigues me. So I dug into the facts and pulled every thread I could find. Along the way I learned that Kevin o' Leary recently won a defamation lawsuit against a prominent crypto influencer who, according to a Florida judge, had falsely accused him of murder and of paying millions to cover it up, among other things. More on that later. But O' Leary was awarded $2.8 million. Now, I am not a huge influencer and I'm already extremely careful about the facts. But from an abundance of caution, let me be clear. There is no evidence of murder in this case and no evidence of a cover up of murder. And legally speaking, this isn't even a criminal matter. Despite early announcements that the OPP's Criminal Investigations Branch was taking the lead with forensic testing on the Olearys boat, possible charges that carried jail time, and the fact that both parties hired criminal defence lawyers. Ultimately, the charges in this case were not criminal. We're going to cover it anyway. This is a case about justice. I'm not a lawyer. I'm just an ordinary Canadian citizen looking at a highly sensationalised case through the lens of the open court principle. I've pieced this two part series together from the public record, including court documents, news archives and trial reporting from the Canadian press, cross referenced with the National Post and the Toronto Star. One final thing, if you know anyone related to this case, please respect their privacy. We'll be back in a moment. Thanks for listening.
- [04:14]
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- [06:11]
Kristy Lee
Every summer, Ontario's lakes come alive in a premier vacation area known as Cottage country, just a few hours drive north of Toronto, traffic permitting. It's a sprawling area with thousands of lakes, known for its natural beauty, lush forests, charming local towns and those iconic Muskoka chairs. Often considered the heart of Cottage country is the Muskoka Region, which centres on three of the largest lakes in the area Lake Muskoka, Lake Rosso and the most star studded with the biggest lots, Lake Joseph One particular stretch of shoreline at the northern end of Lake Joseph has the nickname Billionaires Row because it attracts super wealthy people looking for a greater level of privacy and seclusion. From the lake, you'll often see a private dock on the shoreline next to what looks like a mid sized family home. It's just storage for their assortment of boats, jet skis and other water toys. What owners like to call the cottage is often a grand mansion hidden behind a lush tree line. Some live there permanently, but there's an even greater number of seasonal property owners who retreat there each summer. Former supermodel Cindy Crawford and husband Randy Gerber own property in the area and so do actors Lisa Rinna and Harry Hamlin, with countless more a list celebrities spotted in the area during the summers. But as far as Canadians are concerned, perhaps the most famous or infamous property owner in the area is Kevin O'. Leary. He's sarcastically known as Mr. Wonderful thanks to his years as a cutthroat investor on the CBC reality TV show Dragon's Denver, followed by its US spinoff Shark Tank. More recently, he's been publicly advocating for Canada to become the 51st state of the US and he acted in an Oscar nominated movie starring Timothee Chamele. Just two months ago, Kevin o' Leary attended the Oscars wearing a silver and black outfit featuring an NBA trading card themed pendant from Tiffany and company. He estimated it to be worth about $26 million. But this isn't about any of that. Well, not directly anyway. On a Saturday evening in the summer of 2019, Kevin O' Leary speedboat was involved in a collision on Lake Joseph, reportedly ramming into a larger boat. One person passed away from their injuries and another was rushed to hospital in critical condition. The first to report the news was tmz, the American entertainment tabloid news outlet, which included the detail that o' Leary speedboat immediately left the scene and was later seized by police for forensic testing. This article got immediate public attention. In response, Kevin o' Leary released the following Late Saturday night I was a passenger in a boat that had a tragic collision with another craft that had no navigation lights on and then fled the scene of the accident. I am fully cooperating with authorities. So he was claiming it was the other boat that left the scene. A few hours later, a rep for the TV personality and businessmen publicly clarified two things. His wife, Linda o' Leary had been driving the boat and she passed a breathalyser test that night, The Ontario Provincial Police, or opp, announced that the critically injured person on the other boat had tragically passed away after the collision. That's two deaths total, along with three others who'd been taken to hospital with injuries and later released. The police spokesperson clarified that both boats left to seek medical attention. This was not consistent with Kevin Oleary's statement that it was the other boat that fled. When the police spokesperson was asked about this discrepancy, there was no comment, nor could they give any details about whether speed or alcohol were factors in the collision. All the police could say at that time was was that the Criminal Investigations Branch was looking for anyone in the area who might have video from around the time of the crash. This sudden flurry of news reports fuelled a lot of online chatter. People were sceptical of Kevin O Leary's story. The first of two Reddit comments summing up the suspicion reads zero chance a guy like him is letting his wifey be the captain of his boat going high speed in the dark. It was him, guaranteed. The second comment does anyone else not believe for a second his wife was driving the boat? Seems to me the likeliest scenario is that he was shit faced and driving, crashed, drove off quickly, then swapped captain hats with his sober wife before returning to the scene. As the speculation continued, a devastated relative of one of the two people who died in the other boat came forward to speak to the Toronto sun on the condition of anonymity. They insisted it was the o' Leary boat that fled the scene of the collision. That relative also questioned when exactly Lynda o' Leary was asked to take the breathalyser. Was it straight after the collision or sometime later? The same article quoted a different source from the other boat's camp who said they were pissed about Kevin o' Leary's aggressive PR campaign to get ahead of the narrative. I mean, we've seen it play out before. Member of the elite class finds themselves in trouble within hours, they've got a team of top lawyers and crisis PR professionals shaping a favourable narrative with a full media strategy. Because they got in early, that narrative gets ahead of the story and it spreads quickly as public interest builds. By the time the actual facts catch up, the public have largely moved on to the next big thing. So it has far less impact. And the first, loudest narrative is the one that sticks. Is this how this Kevin o' Leary boat crash was going to go? The following month, the online speculation went into overdrive when the Ontario Provincial Police announced that after a third a thorough investigation they had charged the drivers of both boats. The driver of the larger boat, Richard Roo, was charged with failing to exhibit a stern navigation light. Roo, a middle aged family doctor, responded to the charges through his lawyer, announcing that he intended to contest the facts and vigorously fight the charge. Seems like serious words to respond to a small infraction that carried a maximum fine of just $150. And the charge and fine related to failing to exhibit a navigation light wasn't the issue. Two people had died as a result of a boat collision in one of the most affluent vacation spots in Canada. Lawsuits would be sure to come. As for the smaller o' Leary speedboat, the OPP announced that driver Linda o' Leary had been charged with careless operation of a vessel without care, attention or reasonable consideration for other persons. This was a much more serious charge and According to the OPP's initial announcement, it carried a maximum penalty of 18 months imprisonment and or a fine of $1 million if convicted. And the O' Learys quickly retained Brian Greenspan, a well respected criminal defence lawyer and the brother of famed lawyer Edward Greenspan. These charges were not criminal, he said. They weren't under the criminal code, but the Canada Shipping act. And about the reports of possible jail time and massive fine. If Lynda o' Leary were convicted of operating a vessel in a careless manner that was a misinterpretation of the act, according to her lawyer. The correct penalty would max out at a piddly $10,000 fine with no jail time. As Linda Olearys lawyer Greenspan described it, the boat collision was a terrible tragedy and they were surprised there were charges at all. He stressed that his client was a cautious and experienced boater who was driving at a reasonable speed that night. He demanded the Public Prosecution Service of Canada correct the misinformation on the public record about maximum penalties for conviction. Several weeks later the PPSC would announce that on review, Greenspan was right. But by that point, each new update had intensified online speculation about what actually happened on Lake Joseph that night. Kevin o' Leary must have thrown his wife under the hull, according to one Reddit user. Other commenters said they expected Kevin to use his wealth and influence to keep Linda out of prison. Others acknowledged it wasn't hard to assume the worst about a guy like Kevin o', Leary, but cautioned against jumping to conclusions before the full facts are known. So that's what we're going to do next. Who was driving the boat? Was alcohol or speed involved in the collision? What's with that Stern navigation light? Did Kevin o' Leary try to cover anything up? Why can no one agree on who fled the scene first? And are any of these things even relevant to what actually happened that night? Let's go back to Lake Joseph on that fateful day in the summer of 2, 2019, to piece together the chain of events that ended in tragedy. The following has been put together from witness testimony. It's Saturday, August 24th of 2019, a sparkling summer day at Lake Joseph with a clear blue sky. For those lucky enough to spend summers there, it's all about enjoyment and relaxation. Days spent boating, swimming, fishing and doing water sports. And the warm evenings are for gathering with friends. That Saturday evening, Dr. Richard Roo is preparing to attend a dinner party. In his mid-50s at the time, Richard is a family doctor from the Buffalo, New York area, close to the Canadian border at Niagara Falls. He's married with four children. Although he's an American, Richard Roo's family has strong ties to Muskoka. According to a profile published on muskokaregion.com in the 1960s, a friend in Buffalo first recommended the area to Roo's father, who was also a doctor. This was long before it was known as a billionaire's playground. The family fell in love and spent their summers there for decades later, they would become heavily involved in area conservation. This summer of 2019, Dr. Richard Roo and his wife Hilary are renting a cottage from his friend Irv Edwards, who happens to own the place next door as well. He's also a doctor. Irv Edwards is Canadian, but he works as an emergency physician in Los Angeles, and he loves to spend summers at the Lake Joseph cottage he purchased about 15 years earlier. It's in Hammer Bay, the same general area as the O' Leary family's cottage. That Saturday evening, Dr. Irv Edwards is hosting a dinner party with an eclectic guest list that includes his best friend, his cousin and plus one Dr. Richard Roo and his wife Hilary and a couple of their friends from Buffalo. The group enjoys an evening of dinner, wine and conversation. Then Irv suggests they take his new boat out a little way into the lake to cap off a successful dinner party. The boat in question is a 23 foot Super Air Nortique, a wakeboard and wake surfboat only purchased about 10 days ago. It seats 13 people, enough room for everyone at the dinner party, plus his housekeeper. It's a warm evening and the water is flat calm. The Super Air Nortique takes off from the boathouse at about 10:45pm Irv Edwards is driving at first, as they move out a little way from the shore, the guests start lying on their backs to marvel at the sky. It's dark, there's no moon that night, but also no clouds, so the stars and constellations really stand out. Irv Edwards wants to do some stargazing of his own. So Richard Roo takes control of the boat. He proceeds slowly. Boating at night is risky. There's no street lights and boats don't have headlights, but they're in no hurry and they're not going that far out. About 150 metres from shore, just south of the tiny Emerald Island, Richard turns the engine off. There's no wind, no waves and no current. The lake is so smooth that the boat barely moves. There are three guests sitting in the bow or front of the boat. One of them is Irv Edwards best friend, Gary Poltash, a 64 year old retired accountant from Florida. Then there's Irv's cousin Murray Walmuth, a retired denturist turned independent healthcare consultant from Toronto. Next to Murray is his plus one, 48 year old Suzanne Brito, a mother of three from just north of Toronto who is separated from her husband. Over the next little while, the 12 guests on the boat enjoy the night sky, floating in absolute silence and serenity. It's almost 11:30 by this point. From the bow of the boat, retired denturist Murray Walmuth hears his cousin Irv joking about his golfing game. He gets up and walks over to get a friendly jab in. Just as he turns to head back to the bow, he suddenly notices another boat in the distance. It seems to be coming towards them. Murray curses. It's probably drunk young people being reckless. They'll turn away at any moment. He's not the only one who notices a change. Irv Edwards hears a revving engine like a fast speedboat. He expects it will pass them by any second now. From behind the wheel, Richard Roo suddenly sees a light in his peripheral vision. It's moving quickly, coming closer. His friends from Buffalo see a small speedboat appear out of nowhere. Holy shit. I think that boat is going to hit us. There's a jarring crack, a loud jolt, and the small speedboat is somehow on top of their boat. Within seconds, all hell breaks loose. Richard Roo hears a male and a female voice on the speedboat, but he can't make out what they're saying. It's chaos. The speedboat slides back into the water and Richard turns on his phone's flashlight to see if anyone is overboard. His eyes are drawn to the front of their boat, the bowel. It's a distressing scene. Gary Poltash, the retired accountant from Florida, has a deadly skull fracture. His brain tissue is exposed, there's a lot of blood. And Suzanne Brito, the mother of three, is unconscious and bleeding from her nose or mouth. Richard is of course a doctor, so he checks for vital signs. Suzanne is not breathing, but she has a pulse. He starts administering CPR and his wife Hilary takes control of the boat. While all this is happening, Dr. Irv Edwards, the owner of the boat, suddenly hears a female voice from the speedboat say something like, oh my God, you struck someone. And then a male voice calls out, Is everyone ok? Irv yells back, no, they are not okay. They're leaving for the shore to get urgent medical attention. Dr. Irv Edwards has just realised his best friend, Gary Poltash has suffered a catastrophic head wound. Gary is unresponsive, still breathing, but it's more like final gasps. Irv Edwards realises his best friend is not long for this world. Murray Walmuth, the retired denturist who'd been sitting between Gary and Suzanne at the front of the boat, is slowly regaining consciousness after the impact knocked him over. The fact that he happened to get up just seconds before the crash likely spared him from a much worse fate. As Hillary drives the boat toward the marina where an ambulance will be waiting for them, her husband continues to give CPR to Suzanne Brito. She starts breathing on her own a couple of times, but then falls back as they dock. First responders put Suzanne on a stretcher and rush her to the ambulance. Gary Poltash doesn't last that long. The 64 year old dies of his injuries on the dock, leaving behind two adult children. That same summer evening in 2019, there's another dinner party happening at a cottage on a different shoreline of Lake Joseph. This cottage is owned by friends of Kevin and Linda o' Leary and they're among the guests. If they had to drive around the lake to get there, it would have taken about 35 minutes. Fortunately, the Oleirys came on their speedboat, a 1999 Cobalt 202 CS. It's a water ski boat that can seat up to six to eight people. And that night there's just three of them. Kevin, Linda and a family friend named Alison. It's a quick and easy journey, only about three kilometres across the lake back to their cottage. Lynda grew up around boats and the water, although not Lake Joseph and billionaires row. Her own family had cottages around Lake Simcoe a larger, less exclusive cottage district closer to Toronto where she'd grown up. Linda O. Leary's father was Albert Greer, a famous Canadian tenor, composer and professor who was also known for his passion for boating and love of the water. He reportedly taught all his children about boats and boating safety, knowledge that Linda passed on to her own two children with Kevin. She's always been very confident on the water, kevin would say. He is not unlike his wife. He did not grow up around boats. He grew up around business. His mother, Georgette, helped her parents run their successful baby clothing business in Montreal, Quebec, where he was born. She was of Lebanese descent and Kevin's father was Irish and the top salesman at the family business, according to a 2012 profile in the Montreala. But Terry O' Leary liked to party and struggled with hazardous use of alcohol. The marriage broke down and he passed away two years later, aged 37. Kevin was seven years old and he was seriously falling behind at school. Later, he would recount being diagnosed with severe dyslexia at a time when learning disorders weren't very well understood. His mother, Georgette, was a take charge kind of person. She put him in an experimental program with a new approach to learning that reframed his dyslexia as a strength, not a limitation. He credits this program for boosting his confidence and shaping his out of the box thinking in business. But as for the main foundation of his success, Kevin o' Leary repeatedly credits his mother herself. Georgette was always disciplined with money. She didn't just save it, she believed in growing it by following the markets and investing. Every week she set aside one third of her paycheck to invest. No exceptions. And her rule was never spend the principal amount, only the interest it generates. It was a mindset that left a lasting impression on Kevin, although he would later say his mother kept the growing value of her portfolio a secret for decades until her death in 2008. While Kevin and his younger brother were still young, Georgette remarried. Her new husband was an economist with a United nations agency focused on promoting business, fair working conditions and human rights. The family moved multiple times for his job, living in Southeast Asia, East Africa and the Mediterranean, where Kevin was shown other cultures and modes of business. But business wasn't what Kevin o' Leary saw for himself. He was a creative guy. He played guitar and had a passion for photography. In fact, he wanted to become a professional photographer. But his stepfather took him aside and advised him to keep it as a hobby, get a university degree instead. By this point, the family was in Toronto and Kevin took his stepfather's advice. He graduated in the late 1970s with an Honours degree in environmental studies and psychology, followed by the MBA program at the Ivy Business School. He did his internship at a cat food manufacturer, watching the same basic cat food paste being repackaged into multiple flavors. He says he learned a valuable lesson from this about successful marketing. It's often not about inventing a new product, but finding a new way to sell the product you already have. Kevin joined forces with two partners to co found an independent television production company in Toronto focusing on sports programming. It's the 80s now, and that's where he first meets Don Cherry, the former hockey player and coach turned controversial TV broadcaster.
- [31:12]
Kevin O'Leary
We love him. You love him, Doc. Jerry in the face. I'm telling you, when you come to the games, keep your eyes on the puck. And I'm telling you, I've seen some awful smacks and it's always a woman yapping away there. Look at the game.
- [31:29]
Kristy Lee
Lots of fans.
- [31:30]
Kevin O'Leary
If you'd have won, you'd have been playing the Rangers. Yeah, if my aunt had nuts, she'd be my uncle. That's like asking me what I want. Except for gonorrhea.
- [31:47]
Kristy Lee
Kevin learned another lesson just from helping produce Cherry's show Grapevine. If you want to be successful on tv, you can't be boring. That TV venture didn't last, but Kevin was already eyeing up his next opportunity. And what happens next is the beginning of the official origin story he would refer to again and again. It's a well known narrative. Kevin o', Leary, the savvy businessman who sold his company for billions of dollars and leveraged that to launch a career as a TV personality with an asshole supervillain Persona. But he's repeatedly asserted that it's not just an on screen Persona, it's actually his real self. He says the only reason he's thought of as an asshole is because he's brutally honest and lives by the motto the truth is the best you can give someone. Here's how he explained it to NBC News.
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Kevin O'Leary
People ask me all the time, why are you so tough? Did you learn that? I said no. It's just dealing with the truth all the time. In business you've got to deal with the truth. You can't make up stuff, it just happens to you. Reality always comes and bites you in the hiney. So why not deal with it from day one?
- [33:08]
Kristy Lee
Look, I wasn't planning to dig into Kevin O. Leary's business track record. It's not really my lane and I typically find Those things pretty boring. But I did peek behind the curtain. I compared the story Kevin o' Leary tells about himself to the story told by his public business records. A different picture starts to emerge, a much messier picture that might help explain why after the boat collision, there was so much skepticism of his version of events. So here we go. Kevin O' Leary wanted in on computers. It was now the mid-1980s and they were the next big thing. He partnered with a computer programmer and launched a software company from the basement of his Toronto home, calling it Softkey. His mother loaned him $10,000 to get it off the ground. But he never wanted to create his own software. His business model was to purchase the rights to existing software for home computers, things like games and other basic applications, bundle it together on a CD ROM and distribute it to the masses at a low cost. Kevin's role was salesman, and he went ham. He started with niche computer stores, convincing them to bundle his CD ROMs with new computer purchases. Then he got them into mainstream retail stores, which was practically unheard of at the time. It was a growth strategy so aggressive that at one point Softke was on the verge of collapsing. It was a stressful time and Kevin often hit up the gym to let off steam. That's where he met Linda Greer, the club's fitness director. She was nine years younger than him and he'd describe her as someone who moved with confidence and purpose. He looked out for her every time he went to the gym and eventually asked her out. They got married in 1990. Meanwhile, at SoftKey, he moved past the rough patch and the company grew, absorbed a number of smaller competitors, then merged with two other software companies in the US Kevin and Linda relocated to Boston, Massachusetts, which is where their two children would be born. The consolidated company was now called Softkey International, and the next phase of growth was a full pivot into educational software. As president of the company, Kevin set his sights on acquiring a major US educational software maker called the Learning Company, known for the game where in the World Is Carmen? San Diego. Problem was, he had a competitor. Another software company was set to merge with the Learning Company. And here is where Kevin o' Leary demonstrated the entrepreneurial mindset he often refers to business is war. He bypassed company management and went directly to shareholders of the Learning Company with a higher bid. It's a bold and highly controversial move, known as a hostile style takeover. But it paid off. Softkey acquired the Learning Company for almost $600 million. Kevin O' Leary technically won that business battle, but the controversy was not over at the Learning Quay, company management who'd been blindsided by the hostile takeover, had concerns about how his company's financial situation had been presented to shareholders. According to a 2012 article in the Globe and Mail's report on business, a forensic accounting firm was hired to examine and audit SoftKey International's books and found indications that the company did make its profits look stronger than they actually were. The forensic accounting firm also identified gaps in the company's financial controls that increase the risk of financial manipulation going unnoticed. In response, Softkey signalled its cooperation by announcing it would bring in a consultancy to fix those problems. Turns out that consultancy was headed by a softkey vice president, a clear conflict of interest, and the auditor was not happy with this fix, so Sofke replaced him with someone else. Kevin o' Leary and his original business partner were still at the helm and decided it was time to retire the name Softkey International. The company rebranded to the Learning Company and left SoftKey in the dust along with its troubled reputation. Four years later, in 1999, Mattel came knocking. The toy giant known for the explosion of the Barbie doll had been in a slump. It was the peak of the dot com boom and Mattel was desperate to get in on it. The CEO believed educational software was the key to future growth, and Kevin O. Leary's company was perfectly positioned to take advantage. This would become the biggest deal of his career, the moment that cemented his billionaire origin story. But for Mattel, it would be a big financial face plant of epic proportions. One of the worst deals in corporate history, according to BusinessWeek, the kind of disaster where you briefly consider feeling sorry for a giant corporation. That's coming up next. Thanks for your support. By listening to these messages from our sponsors, it helps us produce the show and give back to people facing injustice like Feed Ontario Food Banks for ending hunger and poverty, who we're donating to this month. Back in a moment.
- [39:45]
Podcast Host/Announcer
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- [40:21]
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- [41:04]
Kristy Lee
Mattel acquired Kevin O. Leary's the Learning Company for the grand sum of about US$3.6 billion. Most of that went to investors and stockholders. So it didn't make Kevin o' Leary a billionaire personally, but it certainly did make him rich and put him on the business map as an emerging leader. Someone to Watch Mattel created a new educational software division and installed Kevin as president, giving him a very high salary, stocks and a generous severance package. But three months later, in August of 99, Kevin sold most of his Mattel stock for about $6 million. It's interesting timing because cracks were already starting to show in the deal. It's a familiar tale. Within weeks, financial auditors found a series of accounting gymnastics that revealed the Learning Company under Kevin o' Leary had not made as much profit as their financials indicated. And worse, the company actually lost money for three consecutive years before Mattel acquired it. So desperate to jump into educational software that they apparently skipped the due diligence part. Just two months later, in October of 99, the toy giant was in serious trouble thanks to its new acquisition. Mattel had to inform their shareholders that not only did they not project a profit from the Learning Company division, but they actually projected a significant loss. It was a shock for shareholders. This announcement alone caused Mattel's own stock to plunge almost to the point of collapse. This didn't really affect Kevin o', Leary, though. He'd already sold most of his own Mattel stock. The following month he was fired from Mattel along with his business partner. He walked away with about $5 million in severance pay on top of the 6 million he got from selling the stocks. Two months later, Mattel reported an actual loss that was far worse than anyone expected. The shock projection was for the learning company to lose between 50 and $100 million that quarter, but it ended up being a loss of 183 million, according to the LA Business Journal. A catastrophe the CEO of Mattel was fired less than 12 months after Mattel first purchased the Learning Company for $3.6 billion. They sold it for just $27 million. It was a massive loss that made major headlines. Mattel's acquisition of Kevin Oleary's the Learning Company was widely described as one of the most disastrous in corporate history. Angry shareholders launched a lawsuit against Mattel and named Kevin o' Leary and his business partner among the defendants, alleging in part that that they'd used accounting manipulations to gain market share and drive up the company's stock price. Mattel settled the lawsuit for 122 million. Salt in the wound but Kevin O' Leary doesn't regret a thing. The way he sees it, the Mattel debacle solidified his reputation as a visionary leader and credible business figure. According to a recent bio, in 2012 he would tell the Globe and Mail's report on business that he was proud of what he'd built. He blamed the disaster on Mattel's mismanagement of his business. After that, Kevin o' Leary tried to buy Atari, which wasn't successful, and he attempted to launch a television channel focused on video games, which never got off the ground. In 2003 he invested money into a self storage company which was sold four years later, netting him $4 million. But even that came with controversy. The deal required him to settle a lawsuit filed against him by the founder of the company. All this time Kevin's wife Linda had been a self described homemaker, running the household and raising their two children while he worked and made the financial decisions. They'd purchased 14 acres of land on Lake Joseph about 10 years earlier, according to a 2010 profile in the National Post. Now it was time to build their dream holiday home or cottage. In 2004 their 9,000 square foot opulent cottage with 10 bedrooms and 11 bathrooms was finished, along with a private dock and matching boathouse. By this point Kevin had set his sights on getting back into tv, this time not as a producer but as on screen talent. It was time to leverage his extensive business success into a public profile. He cold called the head of Canadian broadcast channel the Business News Network, or bnn, and told them that he belonged on the air. It was another aggressive move that made a big impression and got Kevin o' Leary an audition. He proved he had the chops. The network head would later describe him as a natural who lit that camera up from the moment he opened his mouth. Before long, Kevin o' Leary was co hosting a business show on BNN where his blunt delivery and sharp one liners helped him stand out. That Persona really took off in 2006 when he was announced as a dragon in CBC's new innovative reality TV show, Dragon's Den. The show was about entrepreneurs pitching their business ideas to a panel of wealthy investors, or dragons, to try to get them to invest. Kevin o' Leary quickly became known as the harsh theatrical investor, the stereotypical reality TV villain who was willing to to say the cruel things everyone else was thinking but afraid to say.
- [47:57]
Kevin O'Leary
Nobody cares. Everybody wants to hug a beaver love away. But when we get into what really motivates everybody at the end of the day, and this is a sad reality, but you got to deal with it, is money. You are an idiot, and that's exactly what you've done. And I'm sorry if you take offense. I am very, very frustrated that you wasted my time. I think damage control is what you should try and do now and look for something else that might work. It's not this. This is a horrible idea. This is the tea from hell. I'm out. You know, here's the thing about me. I always tell the truth. You haven't sold any more than 30,000. I'm starting to get on my nerves. Listen, here's how you're lying. You go downstairs, you come into my kitchen, buddy, you got to take the heat. This is not your kitchen. It's a TV show. This is my money. You want to get to this side
- [48:41]
Podcast Host/Announcer
of the state, we can do whatever we want.
- [48:42]
Kevin O'Leary
It's a big option for me, and I'm being honest about it. That's what's so wonderful about me. I don't lie. I don't care about your feelings. I care about your money. You're not. You can lead. You be Mr. Nasty. All right, Mr. Wonderful.
- [48:55]
Kristy Lee
I don't want to touch it with a 10.
- [48:56]
Kevin O'Leary
Are you in for 100?
- [48:57]
Kristy Lee
The origin of his nickname, Mr. Wonderful, is from the very earliest episodes of Dragon's Den.
- [49:04]
Kevin O'Leary
If you're the only dragon that tells the truth, you are truly Mr. Wonderful. And as a result of all, always staying on the path of the truth. I'm even more wonderful today than I was then. I'm Mr. Wonderful. Wonderful.
- [49:17]
Kristy Lee
Dragon's Den quickly found its audience and would grow into one of the most successful programs in CBC history. And Kevin o', Leary, one of its breakout stars. It didn't even matter if the deals he made on the show or walked away from had mixed results. His confrontational Persona was Irresistible to the audience, including me. Dragons Den was actually the first Canadian TV show I discovered when we first moved here in 2009. I watch reruns in between job applications because nothing motivates you to get a job like seeing someone else get roasted for their business plan. And Kevin o', Leary, I loved him. Turns out I'm a sucker for a reality TV villain. I even liked Donald Trump on the Apprentice. Please keep listening. Anyway. Of course, the on screen Persona that Canadians found entertaining also created controversy. Kevin o' Leary pushed past the boundaries of what the CBC would normally expect from on air talent, often making inflammatory remarks that drew complaints. The CBC largely defended his role by referring to him as a commentator, not a journalist. By this point, he was no longer just a businessman on television. He was a prominent Canadian media figure whose brand depended on being provocative, polarising and impossible to ignore. He started looking for ways to further monetize his newfound fame. In 2008, two years after Dragon's Den premiered, he launched an asset management company called o' Leary Funds, where once again, he was the salesman, partnering with a licensed asset management firm. While he leveraged his fame to raise significant money, the fund faced issues related to performance management and governance. Critics pointed to a familiar pattern of bold marketing promises that sometimes had questionable results. Kevin would eventually sell the firm to one of his co stars. On Dragon's Den. In 2009, TV producer Marc Burnett called Kevin out of the blue and invited him to a vaguely worded business meeting. Burnett is a huge deal, the man behind wildly successful reality TV shows like Survivor and the Apprentice. Here's how Kevin describes what happened next.
- [51:51]
Kevin O'Leary
He said, look, I'm doing this show called Shark Tank and I'm looking for a real asshole and you're it. Those were his exact words. And I said, well, I don't know whether to take that as a compliment or not. Of course, the next day we shot the pilot and wow, look what happened.
- [52:08]
Kristy Lee
That was in 2009, and Kevin agreed to do Shark Tank while still remaining on Dragon's Den.
- [52:19]
Kevin O'Leary
I like to have people like you doing all the work so I can sit at home, eat bonbons. You've got a real business, but you're a pig. You're greedy. You're not leaving anything for me to wet my beak with. Encourage the person. I told her the truth and I'm proud to do it and I'll do it again. Wow. That's it. End of story. We swim in different waters. I don't want to talk about it anymore.
- [52:46]
Kristy Lee
It too became A massive hit, skyrocketing his on screen talent brand out of Canada and into the stratosphere. But apparently this put a wedge in his marriage. In a 2011 interview with the Globe and Mail, he revealed that he and Linda separated during this time and his TV career was largely to blame. But he was not going to apologise for it. Money equals freedom, he said. You may lose your wife, you may lose your dog, your mother may hate you, none of those things matter. What matters is that you achieve success and become free. Then you can do whatever you like. The separation only lasted two years. Kevin would later tell Toronto Life that he, quote, did the LA celebrity overboard thing and it got tired pretty Damn fast. In 2011, Kevin O. Leary's appearance on a CBC News segment resulted in hundreds of complaints about him. It was about Occupy Wall street and his opponent, Pulitzer Prize winning author and journalist Chris Hedges, argued that the movement was needed to protest economic inequality, corporate greed and the influence of money in politics. Kevin o' Leary is in favour of those things and the interview did not go well. Here's part of it, edited for clarity and brevity.
- [54:19]
Kevin O'Leary
We are on the cusp of perhaps another major banking crisis. There's been no restrictions, no regulations of Wall Street. They've looted the US treasury, they've played all the games that they were playing before and we're about to pay for it all over again. Listen, don't take this the wrong way, but you sound like a left wing nut bar. If you want to shut down every corporation, every bank, where are you going to get a job? Where are you going to work? Where's the economy going to go? Somehow attack this critique by calling someone a nutcase, engages in the kind of trash talk that's polluted the corporate airways. Excuse me. Let's debate the issues then. You were the one who started it. You weren't debating. I called you a nutcase. I called you a nutcase. You said you sounded like a left wing nutcase. Yes, Bar. Okay, that's an insult. And.
- [55:13]
Kristy Lee
After all the complaints, the CBC ombudsman found Kevin in violation of their journalistic standards and the public broadcaster issued a private apology to Chris Hedges. But Kevin o' Leary himself did not have to apologise. And he didn't. In fact, the only consequences he faced was a boost to his personal brand. All publicity is good publicity, after all. There were many instances where Kevin's on screen comments drew complaints. One notable one was on The Lang and O' Leary Exchange, a CBC business show he co hosted with Amanda Lange in 2014, she brought up the topic of extreme global wealth inequality. And things went off the rails again. Edited for clarity and brevity.
- [56:05]
Kevin O'Leary
The combined wealth that's, according to Oxfam,
- [56:08]
Kristy Lee
of the world's 85 richest people is equal to the three and a half billion poorest people.
- [56:15]
Kevin O'Leary
It's fantastic. And this is a great thing because it inspires. Everybody gets the motivation to look up to the 1% and, and say, I want to become one of those people. I'm going to fight hard to get up to the top. This is fantastic news and of course I applaud it. What can be wrong with this?
- [56:29]
Kristy Lee
Really?
- [56:30]
Kevin O'Leary
Yes, really. Somebody living on I celebrate capital a
- [56:33]
Kristy Lee
day in Africa is getting up in the morning and saying, I'm going to be Bill Gates.
- [56:37]
Kevin O'Leary
That's the motivation.
- [56:38]
Kristy Lee
Everybody needs motivation. I just need to pull up my socks. I don't have socks.
- [56:43]
Kevin O'Leary
Look, don't tell me that you want to read.
- [56:45]
Kristy Lee
That was 2014. Six months later, Kevin O' Leary left the CBC altogether. In Canada, he was effectively a big fish in a small pond. But over in America, the pond was much, much bigger. And while he had property in Toronto, his primary residence was still in Boston, Massachusetts. So now he could focus on continuing to grow his profile in the US as well as his various business interests and new opportunities. In 2017, Kevin O' Leary formally entered politics, running for leader of the Federal Conservative Party of Canada. Drawing from Donald Trump's successful campaign messaging that won him the 2016 election, Kevin positioned himself as an outsider businessman who could shake things up. He announced, people are tired of politicians spinning them bs. They're done. Canadians did not know what to make of it. Was Mr. Wonderful actually serious, or was it some kind of stunt for publicity? Kevin o' Leary had branded himself as a straight talker who could stop the political bs. But his actual platform turned out to be, well, the usual bs, just with better lighting. He wanted lower corporate taxes for businesses to keep more profit instead of passing it on to the government. Great for him. But for ordinary people, that means less money to invest in hospitals and healthcare, schools, transit, public services and supports. Kevin also campaigned on cutting business regulations, which again, is great for him and his peers. But for everyone else, those regulations are what stop working workers from getting hurt on the job, stops companies from doing dodgy stuff like poisoning waterways and financial disasters from wiping out people's savings. So while Kevin o' Leary was promising the public he'd cut through the bs, his actual policies only benefited those at the top. It would be Everyone else that would pay the cost, including ordinary workers and families. But his campaign only lasted for a few months. Apparently his polling numbers weren't bad. But he suddenly dropped out, citing a lack of support in Quebec. There'd been questions about whether he could adequately speak both English and French, a requirement for federal politicians. By the time of the boat collision two years later, Kevin o' Leary had solidified a polarizing reputation shaped by aggressive salesmanship, strong personal branding and questions about what was real and what was just smoke and mirrors. Public reaction to his involvement in the boat collision was never going to be neutral. Linda O', Leary, by that point, 56 years old, pleaded not guilty to the charge of careless operation of a vehicle under the Canada Shipping Act. But she did not testify herself. The official, more detailed version of what happened that night from the perspective of the O' Leary speedboat, came from Kevin O' Leary himself. At his wife's 2021 trial, their defence lawyer, Brian Greenspan, announced that Kevin would be the only defence witness because Oliver, Linda deserves to be exonerated. So 65 year old Kevin O' Leary took to the witness box, or rather he testified via zoom from LA about that Saturday, August 24th of 2019, how he, Linda and a friend took their speedboat across the lake to attend a dinner party at a cottage owned by friends. He testified that he knows how to drive the boat, but he's not a boating guy. He's not very good at docking it like his wife is. Linda was from a boating family and she's meticulous about boating protocol and safety standards. That's why she almost always takes the wheel of their speedboat, he said. So let's go back to that evening, to the dinner party the o' Learys attended across the lake before the tragic collision on the way home. Back in a moment.
- [61:41]
Podcast Host/Announcer
This episode is brought to you by Progressive Insurance. Do you ever think about switching insurance companies to see if you could save some cash? Progressive makes it easy to see if you could save when you bundle your home and auto policies. Try it@progressive.com Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states.
- [62:01]
Kristy Lee
Hannah, I just Venmo'd you for dinner. Obsessed. I'm literally spending right now on the lip gloss that's been sitting in my cart. What do you mean, spending it right now? You instantly spend your balance with the Venmo debit card. Stop. Say more. More. Exactly. The more you do with Venmo, the more you get, like, earning up to 5% cash. Back with Venmo Stash get the Venmo debit card or check out online. Venmo Stash Bundle terms and exclusions apply. Max $100 per month. See terms at Venmo Me Stash Terms Venmo Checkout not available at all merchants. The Venmo MasterCard is issued by the Bancorp Bank NA. Kevin o' Leary maintained his wife almost always takes the wheel of their speedboat, including that evening, and there's security footage from the dock where the dinner party was being hosted. The footage shows the O' Learys arriving via speedboat earlier that evening at about 7:15pm the owner of the cottage is waiting for them on the dock. Linda is in the front driver's seat, which is on the right of the boat next to the dock, and she's clearly driving it. As they pull in, Kevin is sitting behind her with their family friend Alison. Linda drives the boat parallel to the dock, then confidently jumps onto it barefoot and ties the bowline. Then she attaches a safety light onto the back of the boat because it'll be dark by the time they leave. The dinner party is hosted by a couple named Leah and Bruce, and Leah testified for the prosecution at the trial. She says she was making welcome cocktails for their guests. Linda comes over and asks for hers to be made super light because she was the designated driver of the boat. Leah says she only uses half the amount of water vodka. She and another friend notice that Linda's wine glass is upside down on the dining room table throughout the meal, and it's still that way when the party is over. During the meal, Linda complains about being the designated driver. Quote I wish Kevin was the dd, but I'm the dd. I'm always the dd. At about 11:25pm the same security camera on the dock shows Kevin and Linda o' Leary getting back into the speedboat with their friend Alison. It's dark now, so things aren't as clear as the previous video when they arrived, but the safety light bar on the end of the boat provides some light. Kevin o' Leary is standing on the dock by the front of the boat holding the bowline. He's wearing a jacket that looks white with sleeves that billow out like a parachute. Linda and Alison are by the back of the boat. You can tell which is which because Alison is taller and is wearing the same flared pants she had on when they arrived, and Linda is clearly taking charge, helping her friend step onto the boat and into the back seat. Then Kevin steps on at the front and moves past the driver's seat to sit in the passenger seat next to it. Only his arm is in view and you can see the white, billowy sleeve. Linda is the last one to step onto the boat and she lands behind the driver's seat, which is clearly empty. She uses her leg to push the boat away from the dock. Now, despite several news outlets reporting that the video shows Linda driving the boat, it's not quite that clear cut. There is no actual footage that clearly shows her in the driver's seat, clutching the wheel as the boat leaves to return home. After she's seen behind the driver's seat, there's a split second of movement that suggests she clambers over behind the wheel just as the boat moves out of view of the security camera. When the video was publicly released, some online commenters interpreted this movement as Linda sitting sideways on the seat while Kevin is driving the boat. But a comparison to the footage of the boat arriving earlier shows Linda driving the boat on the seat closest to the dock. This is the same seat she's standing behind. Later, as her leg pushes the boat away and then she appears to climb
- [66:53]
Kevin O'Leary
in,
- [66:56]
Kristy Lee
there's another camera further down the dock that picks up the boat moving further away before it turns and takes off. The safety light is clearly visible on the back of the boat. And while you can't make out who's in the driver's seat at the front, you can see the same billowy jacket Kevin was wearing in the passenger seat. For these reasons, the prosecution and the defence agreed that Linda o' Leary was driving the boat when they left the dock. The crash happens just five minutes later. But while it seems we can put that matter to bed, there are a number of other issues involved in this collision. All of the following is from trial testimony. Kevin O' Leary describes that Saturday, August 24th of 2019, as a beautiful night, but a dark night. He says the boat was planing, which means it was traveling at speed, with the hull lifted partly out of the water and skimming along the surface. There was no moon and the lake was in complete darkness, so they couldn't see anything. Suddenly, they hit something that Kevin testified had been completely invisible in the darkness until they went wrong right into it. He described it as almost having a shroud on it or something. He says the minutes after that are chaotic, same as the Edwards boat. They did not know what happened. Both he and Linda call out to the other boat to see if everyone was okay, but they don't hear any response. Kevin's immediate focus turns to their friend Allison, who is bleeding from a head injury. But then the other boat suddenly lights up like a Christmas tree. According to Kevin it was huge. It was like a torch being lit. You have to work very hard to make a boat of that size be that dark. The boat started moving and drove away from the sc. Gary Poltash, the 64 year old retired accountant from Florida, passed away minutes later on the dock. His body was flown back to Los angeles for burial. 48 year old Suzanne Brito was rushed to hospital with devastating head injuries. She remained on life support long enough for her organs to be donated. According to the Toronto sun, she passed away on the Monday two days after the collision. Suzanne left behind two sons and a daughter aged just nine to 12 years old, as well as her husband and her parents and siblings. Hundreds reportedly attended Suzanne Brito's funeral. The mayor of Uxbridge, the community just north of Toronto where she lived, told CBC that Suzanne and her family were active in the community and her energy and enthusiasm would be missed by all who knew her. Suzanne was often called Susannah and friends remembered her as a devoted mother who was beautiful inside as she was on the outside. Her sister described her as joyous, a nature lover. Her motto was to live life to its fullest. In an interview with a US media outlet, Gary Poltash's adult daughter remembered him as an avid sports fan with deep roots in Southern California who worked hard to provide for his family and be present in their lives. Lake Joseph was one of his favorite places on earth and she took comfort from that quote. He lived his life up until its final moments to the fullest. Gary Poltash's family started a GoFundMe for a scholarship to benefit Suzanne Brito's children. Gary's adult son wrote that since his father was a true believer in the power of education, they felt this was an appropriate way to honour and respect his values. Although we never got to meet her, we're told that Susanna and my father became friends, fast friends, while enjoying the beauty of the lake. An image was posted of Gary and Susanna on a boat on the lake, likely taken earlier the day of the collision. Suzanne is smiling at the camera and Gary is laughing broadly. Three months after the collision in November of 2019, the first of a series of wrongful death and injury lawsuits were filed. Suzanne Brito's family, including her three young children and husband, her parents and siblings, as well as members of Gary Poltash's family, alleged that the deaths were the result of negligence in the operation of both boats. As a result Suzanne's children lost their mother's guidance, care and companionship and were asking for $2 million in damages from both Kevin and Linda O' Leary and Richard Roux and Irv Edwards. Several news outlets published details of the lawsuit focusing on Kevin and Linda o' Leary because of their public profile. It alleged that either one or both of them were responsible for driving the speedboat with an arrogance and a callous disregard regard for Suzanne Brito's rights. It accused the o' Learys of being impaired by alcohol and drugs, distracted by electronic devices, lacking proper boating licenses and failing to wear corrective glasses despite poor vision. It alleged that Linda o' Leary was driving too fast and failed to keep a proper lookout, that she failed to take action in response to the horn sounding from the Edwards boat and drove directly into its path. As for Kevin o', Leary, the claim alleged he either failed in his own duties on the boat or negligently allowed his wife to operate it when he knew or should have known that she was inexperienced, unsafe and incapable of operating it with proper care. These were just allegations in the Statement of Crime claim none of them had been proven in court and the origin of many of them is unknown. At Lynda o' Leary's later trial, it was established that she was an experienced and licensed boat operator. There's been no evidence of a horn sound prior to the collision, nor evidence of distraction from electronic devices or vision problems that required corrective glasses that they failed to wear. But possible alcohol impairment and the speed of the o' Leary boat was part of the trial proceedings. Of course, the o' Learys weren't the only ones named. Irv Edwards, the boat owner, and Richard Roo, who was driving that boat, were also named, but no details of the allegations against them were publicly released. So what's the deal here? Was the Edwards boat just floating on the lake without any lights on at all while their 12 passengers were stargazing? Thanks for listening. In Part two, we continue to examine what happened on the Edwards boat and the sequence of events that unravelled at the o' Leary cottage in Mount immediately after the collision. A reminder that Linda Oleary's charge and trial did not fall under the Criminal Code, but the Canada Shipping Act. And again, if you happen to know anyone related to this case, please respect their privacy. Part two will be available in a week if you're subscribed to our ad Free premium feed on Apple Podcasts. Amazon Music included with prime or Patreon. Look out for early release if you found this episode compelling. Please tell a friend, post on social media or leave a review wherever you listen to podcasts. This series has been pieced together from court documents, the news archives and most notably, the trial reporting of Holly Mackenzie Sutter for the Canadian Press, Betsy Powell for the Toronto Star and Adrian Humphries for the National Post. For the full list of resources, visit canadiantruecrime CA and follow us on Facebook and Instagram for updates. Canadian True Crime donates monthly to those facing injustice. This month we have donated to Feed Ontario food banks for ending hunger and poverty. Audio editing was by Crosby Audio and Eric Crosby voiced the disclaimer. Our senior producer is Lindsay Aldridge. Research, writing, narration and sound design was by me and the theme song was composed by we talk of dreams. I'll be back with another Canadian True Crime episode. See you then.
- [77:11]
Podcast Host/Announcer
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- [77:40]
Kristy Lee
law Hannah, I just Venmo'd you for dinner. Obsessed. I'm literally spending it right now on the lip gloss that's been sitting in my cart. What do you mean spending it right now? You instantly spend your balance with the Venmo debit card.
- [77:51]
Kevin O'Leary
Stop.
- [77:52]
Kristy Lee
Say more. More. Exactly. The more you do with Venmo, the more you get. Like earning up to 5% cash. Back with Venmo Stash. Get the Venmo debit card or check out online. Venmo Stash Bundle terms and exclusions apply. Max $100 per month. See terms at Venmo Me Stash Terms. Venmo Checkout not available at all. Merchants the Venmo MasterCard is issued by the Bancorp Bank n a.