Kevin O'Leary's Boat Collision [1]
Canadian True Crime
Kristi Lee
4.7 • 5K Ratings
🗓️ 18 May 2026
⏱️ 73 minutes
🧾️ Download transcript
Summary
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
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Transcript
Click on a timestamp to play from that location
| 0:00.0 | Welcome to Canadian True Crime, a completely independent project funded mainly through advertising. |
| 0:05.8 | To listen, add free and early, subscribe to our premium feed on Amazon Music Included with Prime, Apple Podcasts, and Patreon. |
| 0:14.1 | This podcast often has disturbing content and course language. It's not for everyone. Please take care when listening. |
| 0:21.2 | Hi there, it's Christy Lee. I hope you're well and thanks so much for tuning in after a longer |
| 0:26.8 | than expected delay. I appreciate it. Before we begin, an important legal note about why I chose |
| 0:33.7 | this case. Every time controversial Canadian businessman and TV personality Kevin O'Leary |
| 0:40.1 | pops up in the news, which is often because Mr. Wonderful loves the spotlight, the comment |
| 0:46.0 | sections fill with references to a 2019 boat collision that caused the deaths of two people. |
| 1:00.0 | Kevin O'Leary built his empire on bluntness and playing a reality TV supervillain. That woman put her life into this for three years. |
| 1:02.0 | Robert. |
| 1:03.0 | You could see it in that. |
| 1:04.0 | So what? |
| 1:05.0 | This is business. Life is hard. Then you die. |
| 1:06.0 | Get over it. |
| 1:07.0 | Well, maybe in your world. |
| 1:09.0 | This sounds terrible, but unfortunately, I have the track record to be this arrogant. |
| 1:14.6 | It's awful. I hate me. |
| 1:16.6 | Hey, that's wonderful. |
| 1:18.6 | But how do I make money off depressed people? |
| 1:21.6 | You know, this is all crap. |
| 1:23.6 | It's not. |
| 1:24.6 | Money and tears don't mix. |
... |
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