Kevin O'Leary's Boat Collision [1]

Kevin O'Leary's Boat Collision [1]

Author: Kristi Lee | Canadian True Crime May 18, 2026 Duration: 1:13:14

A two-part series | “Mr. Wonderful” built an empire on bluntness and being the reality TV villain we love to hate. So when his speedboat collided with another boat on Muskoka's "Billionaire's Row" - leaving two people dead, the public was ready to assume the worst of him.


Early reporting - and Kevin O’Leary’s own response to the tragedy - sparked suspicion that he’d “thrown his wife under the hull”, and was using his wealth and influence to control the narrative.


In this series, we go back to the summer of 2019 to trace the chain of events that ended in tragedy on Lake Joseph, examine all the evidence, and explore why conspiracy theories continue to thrive long after the case was legally closed.


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IMPORTANT:

– If you know anyone related to this case, please respect their privacy.

– This series does not frame this incident as a "crime" - the charges ultimately fell under the Canada Shipping Act.

– This series has been pieced together from the public record, including court documents, online news sources and daily trial reporting.

– Our intention is to look beyond the headlines, rumours and conspiracy theories surrounding a highly publicized boating tragedy, and carefully examine the evidence to better understand what happened. 

– Kristi Lee is not a lawyer, but a member of the general public reviewing this case through the lens of the open court principle.

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Part 2 will be available to all in a week. Look for early, ad-free release on CTC premium feeds: available on Amazon Music (included with Prime), Apple Podcasts and Patreon.


Canadian True Crime donates monthly to those facing injustice. This month we have donated to Feed Ontario - a charity that supports food banks across the province to help end hunger and poverty.


Full list of resources, information sources, and more:

www.canadiantruecrime.ca/episodes/212


Hosted on Acast. See acast.com/privacy for more information.


Canadian True Crime is a podcast that explores the nation's most compelling criminal cases, hosted by Kristi Lee. This isn't just a recounting of facts; it's an immersive deep dive that moves from the snowy streets of small towns to the darker corners of major cities. With meticulous research and a trauma-informed perspective, Kristi goes beyond the sensational headlines. Each episode weaves together the intricate details of a case with the broader social and historical forces at play, aiming to unravel not only what happened but why it happened and the profound impact on those affected. Listeners will hear a thoughtful, detailed examination of true crime that respects the gravity of the subject matter while seeking a deeper understanding of the stories that have shaped communities across the country. The podcast provides a narrative journey that is both specific in its focus on Canadian cases and universal in its exploration of human nature and societal structures. By focusing on thorough research and contextual storytelling, Canadian True Crime offers a listening experience that is engaging, respectful, and consistently compelling for anyone interested in the complexities of real-life mysteries and the Canadian context from which they emerge.
Author: Language: English Episodes: 100

Canadian True Crime
Podcast Episodes
Kevin O'Leary's Boat Collision [2] [not-audio_url] [/not-audio_url]

Duration: 1:27:46
[Part 2 of 2] In 2019, a late-night boat collision involving Kevin and Linda O’Leary on Ontario’s Lake Joseph, left two people dead and sparked years of intense public scrutiny and conflicting narratives.In part two, we…
Production delay: new episodes coming soon [not-audio_url] [/not-audio_url]

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Colin Thatcher and the murder of JoAnn Wilson [2] [not-audio_url] [/not-audio_url]

Duration: 1:15:39
[Part 2 of 3] As she recovers from her gunshot wound, JoAnn Wilson decides to back down from the custody fight with her former husband.Colin Thatcher has won this battle, but his fixation is far from over. A series of wi…
Colin Thatcher and the murder of JoAnn Wilson [replay] [not-audio_url] [/not-audio_url]

Duration: 1:10:52
A three-part series—A man walking home from work suddenly hears screams coming from a house... then a single sharp crack.He follows the sound to the garage, where he finds a woman bleeding out on the floor. It's JoAnn Wi…
The Twisted Story of Sergeant John Wilson [2] [not-audio_url] [/not-audio_url]

Duration: 1:01:34
[Part 2 of 2] After picking up his pregnant wife from Saskatoon train station, Sergeant John Wilson drives them north to their new home.They just have one stop to make on the way to take care of some "police business"...…
The Twisted Story of Sergeant John Wilson [replay] [not-audio_url] [/not-audio_url]

Duration: 1:02:46
A two-part series—A gripping, action-packed miniseries about a mountie who finds himself at the centre of a sordid love triangle.Pieced together from a treasure trove of real love letters, forged letters and police and c…
Quick update: new episodes return in April [not-audio_url] [/not-audio_url]

Duration: 4:40
A quick update and some thanks! Over the past 12 months... Canadian True Crime has had the opportunity to take on several meaningful projects alongside the usual podcast production. These included the CBC documentary Bre…