Muskoka is Ontario’s most coveted cottage-country region, with its vast swaths of towering jack pines and deep, clear waters, and all within a two-hour drive—or 30 minutes by floatplane—from downtown Toronto. Among Muskoka’s three main lakes, Joseph is the smallest and most exclusive, its shoreline dotted with summer homes so splendid they make a mockery of the term cottage. And yet, even by monster-cottage standards, the residence of Kevin and Linda O’Leary stands out.
The three-storey, 9,800-square-foot mega-chalet, painted in soft grey with white trim, perches high on a promontory of Canadian Shield, looming imperiously over 345 metres of rocky, pine-forested shoreline. Inside are 10 bedrooms, 11 bathrooms and a turreted staircase winding up to a master suite with ensuite and a private deck. In the great room, a pink granite fireplace soars 32 feet to the pine ceiling. The furnishings are suitably grand, with “an antique in just about every room,” as Linda once boasted to a National Post reporter. Off the main cottage is a broadcast room from which Kevin beams in for newscast cameos and Zoom calls, and, nestled in the woods, an artist’s shed, where he paints. Down at the water, the boathouse, painted grey and white to match the main cottage, is big enough to accommodate a large family but is in fact occupied by an ever-expanding collection of pricey water toys, including—at least until one calamitous, heartbreaking day last August—an 18-foot Cobalt bowrider.
Kevin, of course, is the Canadian venture capitalist and erstwhile political aspirant also known, ironically, as Mr. Wonderful on the American reality show Shark Tank. He has a large social media presence, including a YouTube channel where he posts regular rants in his signature irascible style about politics, business, pop culture and whatever else is on his mind. While Kevin built his business, Linda, his wife of 30 years save for a two-year separation in 2011, stayed home to raise the kids (Savannah, a New York–based video producer, and Trevor, a McGill engineering student, are both now in their mid-20s). More recently, Linda has taken up the role of VP of marketing of the family’s private label, Kevin O’Leary Fine Wines.
The penultimate Saturday of August 2019 was a spectacular cottage day at the end of a perfect summer. The O’Learys enjoyed a clear morning, which gave way to a bright afternoon, the temperature hanging in the low 20s, any trace of humidity dispersed by a cool breeze off the lake. As the sun touched the horizon, a chill entered the air, and soon after that, Kevin and Linda, accompanied by a friend, a woman from Toronto, piled into their Cobalt and headed northeast, across the mouth of Hamer Bay, to the cottage of their friend Bruce Smith for a dinner party. Around 11 p.m., the party wrapped up, and Linda got behind the wheel of the Cobalt to drive home. According to documents unsealed last October, police believed that Linda had been drinking before getting into the boat. Her lawyers didn’t dispute that claim, but they contend that alcohol played no role in what happened next.
The O’Leary party retraced their route, travelling southwest toward their cottage. Like her husband, Linda was an experienced boater, having spent over a quarter of a century summering on the lake. She knew the waters well. Perhaps it was because of this familiarity that she drove the boat at what police later characterized as “significant speed”—the exact speed wasn’t specified.
Around the time the O’Leary party set out, a separate, much larger dinner party had wrapped up nearby. This one was hosted by Irv Edwards, a Canadian-born ER doctor and businessman who lives in the U.S. and spends summers on Lake Joe. Edwards had just bought a pontoon boat, a low-speed pleasure cruiser. He and 11 others headed out into the open water to stargaze. In Canada, navigation lights—green at starboard, red at port and a white light at the stern, viewable from 360 degrees—are required by law after sunset, but shortly after the Edwards boat set out that night, video evidence from Edwards’s dock shows that the navigation lights on the pontoon boat were switched off, perhaps to cut down on light interference and give a better view of the night sky. Whether they were later switched back on is a matter of intense disagreement.
Seated in the bow of the pontoon boat was a slim, handsome, silver-haired man named Gary Poltash, a 64-year-old former accountant from California who had retired to Florida. Beside him was Suzana Brito, a 48-year-old married stay-at-home mother of three from Uxbridge, Ontario. A much-circulated photo shows them looking windswept and flushed with health, waterproof jackets zipped to the chin. Poltash is laughing uproariously at someone’s joke while Brito gazes just past the camera, smiling wistfully.
A short distance from shore, Edwards turned over control of the pontoon boat to his friend Richard Ruh, a general physician from Orchard Park, an affluent suburb of Buffalo. The Ruh family had spent summers on the lake for generations, long before it became a billionaire’s playground. His love of the area ran deep—he and his extended family had helped preserve a large tract of land from development by raising funds from nearby cottagers. With Ruh at the helm and the engine turned off, the lake was serene, the shoreline indiscernible from the dark lapping water.
The quiet was broken by the roar of the O’Learys’ Cobalt bearing down on the pontoon boat. Susan Auricchio, a friend of Edwards’s also from Orchard Park, was on the pontoon boat that night. By the time they heard the oncoming vessel, according to Auricchio’s statement, it was already too late. The Cobalt slammed into the pontoon boat’s starboard bow, then travelled up and over it, killing Poltash on impact and knocking Brito unconscious with a catastrophic head wound. The injuries on the O’Leary boat were insignificant by comparison: Linda sustained an ankle injury, and her friend suffered a minor head wound. Kevin was unhurt.
The pontoon boat was in chaos, its bow covered in blood. While the doctors, Ruh and Edwards, attended to Poltash and Brito, there was a brief exchange between the boaters. According to passengers on the pontoon boat, the O’Learys didn’t identify themselves, though one of Edwards’s guests later told police she recognized them. The O’Learys’ lawyer confirmed that “maybe a word or two was said” but that in the chaos of the moment no significant information was exchanged. The passengers on the Edwards boat said they needed to go to the nearby Rocky Crest Golf Resort to meet paramedics and quickly departed. The O’Learys, whose boat had a damaged hull, proceeded directly to their dock a few hundred metres away.
In 2017, Kevin O’Leary posted to Facebook a photo of the lights of his dock glowing on the inky lake, with a portentous caption: “Boating at night freaks me out so it’s good to see the boathouse lights because it means we made it home alive!” Ontario is blessed with a vast network of freshwater lakes and waterways, and people, understandably, enjoy travelling on them, especially in summer. Yet that pastime comes with inherent risks. In Ontario, there’s an average of 24 fatalities per year on OPP-patrolled waters—which excludes jurisdictions that have their own police force, like Toronto. This year is proving to be just as dangerous. By the end of July, there had already been 15 boating deaths, putting the province on track for 24, and potentially more as pandemic-stressed urbanites flock to cottage country for a little R and R.
Yet despite the obvious risks, Ontarians have historically displayed cavalier attitudes about boating. As late as the 2000s, long after DUI awareness campaigns had shamed drunk drivers into handing over their keys, on-board boozing remained the norm. Despite a steady creep of regulations—including an online certification program that’s notoriously easy to pass—the lakes of cottage country become the Wild West in summer. And when you take a dangerous pastime and do it during the night, the risks are exponentially elevated. The O’Leary crash was only the most high-profile recent example of a tragic problem that the OPP has tried to combat for decades.
Who was to blame for what happened that night? When two boats collide, the place to start is usually the right of way rules under the shipping act. Because the O’Leary boat approached the starboard side of the Edwards boat, the rules dictate that the pontoon boat was expected to change course to avoid collision; however, if the pontoon boat didn’t change course—and with its engine off, it wouldn’t have been able to, at least not quickly—then the O’Leary boat was expected to alter course to prevent a collision. And were that the end of the story, the matter might be relatively straightforward.
The O’Learys, however, insist that the Edwards boat’s navigation lights were switched off at the time of the collision, thereby absolving Linda. How could she have been expected to obey right of way rules for a boat that was effectively invisible? Ruh, who was behind the wheel of the pontoon boat, has a different point of view. He claims via his lawyer that the boat was “lit to the legal requirement” at the moment of impact, a claim backed up by at least two of his passengers.
According to boating safety expert John Gullick, at night, lights on a stationary boat can often be mistaken for faraway shore lights and give the approaching boater the false impression of open water ahead. If Ruh is correct that the lights were switched on, perhaps Linda mistook them for shore lights; if the lights were off, it’s possible the O’Learys didn’t see the boat at all.
At some point after the O’Learys arrived home—the exact timeline has not yet been made public—their son, Trevor, called 911. Soon after that, still in the early hours of Sunday morning, Constable Michelle Ingham of the West Parry Sound OPP arrived at the O’Leary cottage. Ingham smelled alcohol on Linda’s breath. On its surface, the case might have appeared open and shut: a man was dead, a woman was in critical condition and the driver of the other boat had alcohol on her breath. But in Ontario, an officer must have evidence of a blood-alcohol concentration over 80 milligrams of alcohol per 100 millilitres of blood to test further and pursue a DUI. Using the same device police use for roadside stops, Linda blew an “alert,” indicating a blood alcohol concentration of between 50 and 80, high enough to trigger an immediate three-day driving suspension—applicable for both road vehicles and boats—but not enough to warrant a drunk-driving charge. (Officers can in some cases pursue that charge when an alert is combined with signs of impairment—slurred speech, red eyes, stumbling and the like.) When Ingham asked Linda what she’d had to drink, Linda explained she’d been served “a vodka drink” following the crash, after arriving at the dock. When asked who’d served it, Linda said she couldn’t remember. That explanation, while perhaps curious for an event that had transpired so recently, is also plausible: she was no doubt rattled—who wouldn’t be?—and perhaps wanted a drink to calm her nerves. With her mind elsewhere, it’s possible she didn’t notice who handed her the drink.
At the same time, the explanation raises questions. Calvin Barry is a prominent Toronto defence lawyer with decades spent representing people charged with drunk-driving offences. Clients regularly call him when they’ve been behind the wheel in a car accident, often where alcohol is involved, to strategize before the police arrive. Drinking alcohol immediately after an accident, he says, makes it extremely difficult for a toxicologist to determine the crucial question of what booze was consumed when. The loophole, which Barry stresses he does not exploit, is often referred to as the “intervening drink defence.” It was a common legal strategy until 2018, when Parliament passed Bill C-46, a controversial measure that makes it an offence to have a blood alcohol concentration of over 80 within two hours of driving. Of course, Linda wasn’t in contravention of that rule because she didn’t blow over 80. “You’ve got to wonder,” says Barry, “why would somebody pound back a drink after being involved in a horrific boat crash?”
After the crash, the OPP sent an officer to observe the O’Leary boathouse to ensure the evidence wasn’t contaminated. Once they’d obtained a search warrant, specialists examined the boat for DNA, fingerprints (presumably to confirm who was driving) and paint transfer to recreate the angle and speed of the collision, and tested the boat for mechanical failings. A crash technician examined the Edwards boat as well. Soon after, the police released a statement confirming that they were investigating a fatal boat crash on Lake Joseph but gave no further details. Then, given the profile of the O’Learys, and anticipating the media circus to come, the police successfully requested that a judge seal the case.
At the hospital, Poltash had been pronounced dead. Brito’s family held vigil, and on the following Tuesday, she died. In the absence of names or other concrete facts, gossip swirled thick on the three lakes, as well as in the nearby towns of Bracebridge and Port Carling. In the end, TMZ broke the story. Three days after the crash, the U.S. tabloid site ran a piece featuring several photos plucked from O’Leary’s Instagram account. One featured the gorgeous Muskoka shoreline leading up to O’Leary’s boathouse near where the crash occurred—a stretch Kevin calls “the wedge” because of the way a jack pine casts a long triangular shadow along the lake. Within hours of the TMZ story breaking, Kevin had shut off public comments on his accounts, and Linda’s Instagram went from public to private. But while they remained silent, privately the O’Learys were in damage-control mode. They retained Brian Greenspan, a criminal lawyer from Toronto known as much for his ferocity in court as for the celebrities he’s represented, among them Naomi Campbell and Justin Bieber. The O’Learys also reached out to private investigators and Kevin’s agent, Jay Sures, the co-president of United Talent Agency and one of the most powerful men in Hollywood. Sures directed media outlets to the statement provided by Kevin’s director of public relations. That statement was a master class in strategic omission: “On late Saturday night I was a passenger in a boat that was involved in a tragic collision with another watercraft that had no navigation lights on and then fled the scene of the accident. I am fully co-operating with law enforcement in their investigation. Out of respect for the victims’ families and to fully support the ongoing investigation, I feel it is inappropriate to make further comments at this time. My heartfelt prayers and condolences to the victims, the families and those affected by this loss.” Reading the statement, the average person might have surmised that the O’Learys had been victimized by a renegade boater in a hit and run.
If Kevin O’Leary had intended to pour water on the fire, the actual effect was dumping gasoline. According to a Toronto Sun story, the passengers on the pontoon boat were “pissed” about the O’Learys’ PR campaign. And a member of the Brito family, speaking on condition of anonymity, alleged that O’Leary was in fact the one who had fled the scene. In Muskoka, the smouldering gossip exploded. The most common theory among locals—unfounded, it would turn out—was that Kevin had been driving drunk, and that Linda was taking the fall for her husband. Mark Clairmont, owner of the news website Muskoka Today, was skeptical about the lights being off. “If you’ve ever been out on a boat on a Muskoka lake at night under that bright starry sky, it strains belief to think they’d need to turn off the lights just to stargaze,” he told me.
Oversight of the investigation was assigned to Detective Inspector Martin Graham of the Orillia OPP. It turned out he and Greenspan had a history. They’d recently faced off in court over a case in which Greenspan had defended the former mayor of Thunder Bay, who’d been charged with extortion. The case was front-page news in Northern Ontario for months. In the lead-up to the trial, Greenspan’s client accused Graham of being an opportunist who was trying to take down a local bigwig to make a name for himself. (Greenspan eventually prevailed—his client was found not guilty in February.) With the O’Leary trial, Graham and Greenspan were once again set up to clash.
Graham and his team began interviewing witnesses and reconstructing the scene, the latter proving complicated given the need to duplicate weather and light conditions on the night of the accident. They asked that members of the public with information pertaining to the case come forward to police.
In the first week of September, just days after Brito’s funeral, which was attended by hundreds of mourners in Uxbridge, Graham took several witnesses from Edwards’s boat back to the scene of the accident. Around the same time, Poltash’s body was flown home and later buried near Los Angeles.
Originally, the OPP filed paperwork that suggested they were pursuing four counts of operating a vessel in a manner that was dangerous to the public, two causing death and two causing bodily harm. The potential penalties for Linda O’Leary were significant—up to 14 years’ imprisonment. But as the investigation continued, Graham and his team had trouble gathering enough evidence to support criminal charges.
A contributing factor was video evidence produced by the O’Learys. They had installed a state-of-the-art security system on their vast property. When Kevin O’Leary viewed the footage, it seemed to show the collision. How clearly and from what angle isn’t known, but some time after O’Leary played it for investigators, they had become confident enough that the Edwards boat was unlit at the time of the collision that they soon charged Ruh with failing to exhibit navigation lights while under way, punishable by a fine under the shipping act.
Meanwhile, Linda was charged with a regulatory violation for careless operation of a vessel, which would mean zero jail time and at most a $10,000 fine. The news was presumably a welcome relief for the O’Learys, but in September, prosecutors informed the media that Linda was facing a million-dollar fine and up to 18 months in prison. The prosecutors, it turned out, had been referencing penalties for commercial travel—ocean-going vessels and the like—rather than small pleasure craft on a lake. It was a mistake, possibly an honest one, but it was too late, and word quickly spread that Linda was facing significant jail time. Detective Graham said not a word. Greenspan normally keeps schtum in the lead-up to court cases, but this time he went ballistic, telling any outlet that would listen that the prosecutor had misinterpreted the law and caused the O’Learys considerable harm. Linda “has always been a cautious and experienced boater who came into collision with an unlit craft on a dark and moonless night,” Greenspan told the Los Angeles Times. “The other boat was sitting in a dark spot on a lake, no cottage lights nearby, no moon.”
Greenspan demanded a correction, but the OPP and the Crown stayed quiet for weeks. Finally, on October 11, Natalie Houle, a spokesperson for the Public Prosecution Service of Canada, corrected the earlier statement via email to reporters. A few days later, Kevin was spotted at LAX, arriving on a work trip. He waved off the cameras but seemed otherwise relaxed and upbeat, smiling and kibitzing with reporters. And why not? His wife was effectively off the hook.
Then, in early November, Suzana Brito’s parents and sister filed a civil suit against the O’Learys, Ruh and Edwards for a total of $1 million. That action won’t be resolved until after Linda’s case wraps up, which won’t happen until this fall at the earliest. If the Britos win, reliable sources close to the case told me a possible outcome is that the insurance companies would pay out. By early July, Poltash’s family had not filed suit, nor had Brito’s husband.
In September, Alex Poltash, Gary’s adult son, started a GoFundMe scholarship for Brito’s three young children. It was, he wrote on the GoFundMe page, the best way he and his family could think of to “honour and respect the values that were near and dear to our father’s heart.” The target was $15,000, and the page raised $25,000 in a matter of weeks before being deactivated.
The case dragged on for months without a significant update. The O’Learys had provided police with video they felt exonerated them, but that still hadn’t expedited the case or caused the entire matter to be dropped. Then, in early March 2020, just before the pandemic hit, Kevin appeared on CP24 to promote his investments, throw some signature shade at a few politicians and address the incident. He described how awful the ordeal had been for his family, and his wife in particular. “I have to watch this every day,” he said plaintively, adding that he also “felt horrible” for the families of the dead. He implored that all forensic evidence be made public. “Let’s get it all out, let’s flush it, with transparency…to put it to rest for all the families,” he said.
Neither Linda nor Kevin responded to my requests for an interview. The same was true of the other parties involved in the crash. In the course of my reporting, I spoke to several nearby cottagers, many of whom passed along what they knew, but most of it was speculation and innuendo. What I did learn: the O’Learys have some defenders beyond the lawyers and agents who are paid to do so. One of their wealthy neighbours told me the couple feel they’re being unfairly persecuted because of their wealth and fame. This neighbour’s view was that the charges against Linda are trumped up, opportunistic and essentially a non-story. “It’s an accident that just happens to involve a famous guy and a bunch of wealthy folks,” he said. The O’Learys also have more than their share of detractors. But as Kevin O’Leary well knows, being disliked is different from being a liar.
This story appears in the September 2020 issue of Toronto Life magazine. To subscribe, for just $29.95 a year, click here.