Kevin O’Leary’s Boat Collision

ONTARIO

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 Kevin O’Leary.

Early reporting - and his 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.

IMAGE: Screenshot from Kevin O’Leary YouTube. Image is unrelated to case.

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IMPORTANT NOTES:

• This series does not frame this incident as a crime. While it was initially investigated and reported as a potential Criminal Code matter (per Toronto Life, August 24, 2020), the charges ultimately laid fell under the Canada Shipping Act.

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

• The intention of this series 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. This series has been pieced together from the public record, including court documents, online news sources and trial reporting by media outlets including the National Post, CBC News and the Toronto Star.

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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.

Credits:

Research, writing, narration, sound design: Kristi Lee
Audio editor, voice of disclaimer: Krosby Audio
Senior producer: Lindsay Eldridge

Music credits:

Theme songs: We Talk of Dreams
All other music from Epidemic Sound and Blue Dot Sessions.

Sources:

Court documents

• O'Leary v. Ragone, 2021 FC 185 (CanLII)

• O’Leary v. Ragone, 2022 FC 749 (CanLII)

• O'Leary v. Ragone, 2026 FC 44 (CanLII)

• Wrongful Death Civil Suit Issued in O'Leary Boat Crash
  (press release by McLeish Orlando LLP)

• Benjamin Armstrong Bitboy Crypto Vs Kevin and Linda O’Leary

Video Evidence - surveillance videos in order of time:

• 7:10 pm - The O'Leary boat arrives at cottage across the lake for dinner party

• 10:41 pm - The Edwards boat pulls away from their cottage; the lights disappear (start of video to timestamp 1:21)

• 11:25 pm - The O'Leary boat leaves the dinner party;Linda appears to be driving

• 11:30 pm - Camera from O'Leary cottage depicts collision in the distance (starts at 1:23)

Legal information

• Canada Shipping Act, 2001 ( SC 2001, c. 26)

• Collision Regulations, C.R.C., c. 1416, CANADA SHIPPING ACT, 2001

• Small Vessel Regulations ( SOR /2010-91)

• Small Vessel Regulations (education course)

News articles

• Kevin O'Leary Says Video is Smoking Gun in Boat Crash, Second Victim Dies(TMZ) 

• The Kevin O'Leary boat crash: What we know and what we don't (CBC News)  

• KEVIN O'LEARY BOAT TRAGEDY: Conflicting stories on fatal collision (Toronto Sun)

• Water complicates the investigation into fatal boat crash involving Kevin O’Leary, expert says (National Post) 

• Kevin O'Leary's wife charged in Muskoka area boat crash that killed 2 (CBC News) 

• Ontario police charge two, including Kevin O’Leary’s wife, in fatal Muskoka boat crash
  (The Globe and Mail) 

• Linda O’Leary faces fine, not jail time in fatal boat crash, Public Prosecution Service now says(National Post)

• Prosecutors overstated penalties Linda O'Leary faces if convicted in boat crash
  (National Post)

• Linda O’Leary won’t receive prison time in connection with fatal Ontario boat crash
  (GlobalNews.ca)

• Kevin and Linda O'Leary sued for wrongful death by family of boating crash victim
  (National Post)

• Unsealed search-warrant documents offer new details on O'Leary boat crash: report
  (National Post)

• Linda O'Leary was not impaired' during fatal boat crash, says defence lawyer
  (National Post)

• Linda O'Leary had alcohol on breath on night of fatal boat crash, warrant documents say
  (CBC News)

• ‘We could not see it, it was completely unlit’: Kevin O’Leary testifies at wife’s trial in Muskoka boat crash(Toronto Star)

• Police documents in Kevin O’Leary boat crash case won’t be given to victims' families before trial(National Post)

• Linda O'Leary trial hears grim detail of fatal boating crash in Ontario cottage country | National Post(CRASH VIDEO HERE)

• Prosecutors look for mysterious vodka drink Linda O'Leary said someone gave her after fatal boat crash(National Post VIDEO)

• Boat had lights on when it was hit by vessel operated by Linda O'Leary: Witness
  (National Post)

• Boat hit by Linda O'Leary was well lit, driver tells court, despite conviction for no lights
  (National Post)

• Woman in O'Leary's speedboat sounded 'pissed or bitchy' after fatal boat crash, court hear(National Post)

• Linda O’Leary's lawyers accuse Crown of not providing proper disclosure from witnesses
  (National Post)

• Careless vs. reckless: Why the Crown likely didn't pursue criminal charges against Linda O'Leary(National Post)

• O'Leary speedboat 'ridiculously close' and driven like 'drunk kids' before fatal crash: witness
  (National Post)

• Linda O'Leary was 'hostile' and 'not co-operative' after fatal boat crash, officer tells court
  (National Post)

• Prosecutors look for mysterious vodka drink Linda O'Leary said someone gave her after fatal boat crash(National Post)

• Police re-enacted fatal boat crash involving Linda O'Leary — and this is what they found (National Post VIDEO)

• 'My heart still races': Police nearly collided during simulation of fatal O'Leary boat crash
  (National Post)

• Ontario police officer tells Linda O'Leary trial about nerve-wracking re-enactment of crash
  (National Post)

• At O’Leary trial, officer describes ‘nerve-wracking’ reconstruction of deadly Muskoka boat crash(Toronto Star) 

• Lack of lighting on hit boat was cause of fatal O'Leary crash, OPP specialist concluded
  (National Post)

• 'Linda O’Leary deserves to be exonerated': Kevin O'Leary to testify at fatal boat crash trial

• 'Nobody drives into a boat they can see': Kevin O'Leary testifies in defence of wife at trial over fatal crash(National Post)

• Photos Show Boat Damage from Kevin O'Leary's Wife's Fatal Crash

• Video shows Linda O'Leary's speedboat collision in fatal crash(National Post)

• Officials trying to reconstruct scene of boat crash involving O’Leary(Citynews )

• Kevin O'Leary involved in deadly boat crash(ABC News)

• No accountability in O'Leary boat crash, says victim's sister(CBC) 

• Linda O'Leary had alcohol on breath following fatal boat crash, documents say(CBC)

• "Shark Tank" star Kevin O’Leary involved in fatal boat crash(Global News)

• Case against Linda O'Leary is a 'house of cards,' defence says in closing arguments
  (National Post)

• 'Alcohol played no part': Linda O'Leary not guilty of careless driving in fatal boat crash
  (National Post)

• MANDEL: Linda O'Leary found not guilty in fatal Muskoka boat crash

• Lawsuits in fatal cottage country boat crash involving Kevin O’Leary finally settled. Here's what we know(National Post)

• What really happened the night of the O'Leary boat crash in Muskoka (Toronto Life)

• The Kevin O'Leary boat crash: What we know and what we don't(CBC News)

• Hundreds attend funeral for Suzana Brito, victim of Muskoka boat crash(CBC News)

• Kevin O'Leary confirms he was passenger in boat involved in double-fatal crash(CBC News)

• Linda O'Leary's case adjourned until Nov. 21 as charges against her amended(CBC News)

• Linda O'Leary had alcohol on breath on night of fatal boat crash, warrant documents say
  (CBC News)

• Prosecutors look for mysterious vodka drink Linda O'Leary said someone gave her after fatal boat crash (National Post)

• Driver of 2nd boat in O'Leary crash convicted of failing to exhibit navigation light
  (CBC News)

• Trial begins for Linda O'Leary, charged in 2019 boat crash that killed two people
  (CBC News)

• Boat hit by vessel driven by Linda O'Leary had lights on at the time of crash, witness says
  (CBC News)

• Linda O'Leary's blood alcohol in 'alert' range after deadly boat crash, officer testifies
  (CBC News)

• Linda O’Leary recorded ‘alert’ on breathalyzer; told officer she had alcohol only after deadly boat crash

• O’Leary blood alcohol in warning range in test after boat crash: officer
  (The Gazette via newspapers.com) 

• Video appears to debunk theory that Kevin O’Leary drove speedboat
  (National Post via newspapers.com) 

• Woman tells court she didn't see Linda O'Leary drink after boat crash that killed 2
  (CBC News)

• Frequently Asked Questions - Alcohol-impaired driving(justice.gc.ca)

• NEW ALCOHOL-IMPAIRED DRIVING LAWS(justice.gc.ca)  

• Warn-range blows mean car loss, suspension(Ron Jourard)

• The "Warn Range" for Impaired Driving in Ontario(Kruse Law Firm)

• New impaired driving laws close loophole but have lawyers up in arms
  (Globalnews.ca - Example case before loophole closed)

• At O’Leary trial, officer describes ‘nerve-wracking’ reconstruction of deadly Muskoka boat crash

• The other boat’s lights were off, OPP reconstructionist testifies at O’Leary trial

• 'My heart still races': Police nearly collided during simulation of fatal O'Leary boat crash
  (National Post)

• Linda O'Leary trial wraps after defence argues other boat's lights were off at time of crash
  (CBC News)

• Careless vs. reckless: That’s the relevant distinction in O’Leary trial
  (National Post via newspapers.com) 

• Linda O'Leary found not guilty in fatal boat crash (CBC News)

• No accountability in O'Leary boat crash, says victim's sister (CBC.ca VIDEO)

• Kevin O’Leary’s wife charged in boat crash that killed 2(CBC.ca VIDEO)

Additional sources

• South Bay native killed in boat crash involving Kevin O’Leary was doting father who balanced career and family, daughter says(Daily Breeze - Gary Poltash)

• Justice system's handling of O'Leary boat crash case a 'slap in the face' for victims' families(CBC News - Suzane Brito)

• ALBERT GREER, C.M. Obituary | 2025 - 2025 (Toronto Star - Linda O’Leary’s father) 

• Hamer Bay Island K preserved by cross-border cottagers and Muskoka Conservancy (Muskoka Life - Ruh family)

• Not Your Average Joe: who cottages where on Muskoka's luxest lake (Toronto Life)

• This Canadian Town Is A Magnet For A-Listers On Vacation— Here Are 8 Celebs That Were Spotted There This Summer

• Dragons' Den S03E02 - video Dailymotion

• Don Cherry Post Game Interview 70's

• Don Cherry - on women at hockey games

• CKVU promo & Don Cherry's Grapevine 1984

• Kevin O'Leary's Most SAVAGE Moments | Dragons' Den Canada

Kevin O’Leary Background

• About Kevin (Political website)

• Kevin O'Leary got choked up sharing the 4 ‘very simple’ investing rules his mother followed for 55 years that put two kids through college (Moneywise)

• The Kevin O'Leary machine (The Globe and Mail)

• Kevin O’Leary Youtube - Why Dislexia might be a superpower

• Kevin O’Leary – from Dragon’s Den to Redemption Inc. (The Montrealer)

• Kevin O’Leary’s tweet about family children’s clothing business

• Kevin O'Leary: He's not a billionaire, he just plays one on TV(The Globe and Mail Report on Business)

• Kevin O'Leary: The shark who swims alone(The Globe and Mail)

• The dragon is in (Winnipeg Free Press Homes)

• Did Kevin O'Leary once wipe out an entire industry?(Canada's National Observer)

• Mattel chief promises report on Learning troubles (CNET)

• Mattel Has Nobody to Blame but Itself for The Learning Co. Fiasco

• Mattel Decides to Put on Sale Software Unit Bought in May (The New York Times)

• TV's Shark Tank Guru: In Real Life, No Business Whiz (TIME)

• Inside Kevin O'Leary's investing fund misadventure(Macleans.ca)

• Hot air: The truth about Kevin O’Leary’s business history(The Globe and Mail)

• Mattel CEO's Report Fails to Ease Investors' Doubts (Los Angeles Times)

• MATTEL-How the Giant Toy Maker Fell So Far So Fast (Los Angeles Business Journal)

• Kevin O’Leary’s video about meeting Mark Burnett (Facebook video)

• Kevin O’Leary’s video about being honest (Facebook video)

• Kevin O'Leary's Brutally Honest Relationship With The Truth | Better | NBC News

• CBC Kevin O'Leary - Occupy Wall Street - Chris Hedges Shuts him up

• O'Leary's 'nutbar' remark breach of policy, CBC ombudsman says(The Globe and Mail)

• Kevin O'Leary Tells All In Dragons' Den Extended Interview
  (CBC.ca Amanda Lang controversy)

• The Political Pearls of Kevin O’Leary(The Tyee)

• Kevin O'Leary is a blowhard, a relentless self-promoter and, maybe, Canada's future leader(Toronto Life)

• ‘Failed politician struggling for relevance,’ Kevin O’Leary’s loud Oscars appearance has banded the internet together to roast him (NOW Toronto)

• Kevin O’Leary credits acting chops to years of convincing people he wasn’t driving the boat (The Beaverton)

Reddit Threads

• r/canada - Linda O'Leary found not guilty in fatal boat crash

• r/canada on Reddit: Report: ‘Shark Tank’’s Kevin O’Leary Was A Passenger On Boat Involved

• In r/canada - Fatal Collision That Killed An American Man On Muskoka’s Lake Joseph On The Weekend

• r/sharktank on Reddit: Sad news: Kevin O’Leary’s boat involved in fatal crash

• r/sharktank on Reddit - What really happened the night of the Oleary boat crash

• r/canada on Reddit - Conflicting stories on fatal Kevin O'Leary boat collision

• r/canada on Reddit: Kevin O’Leary credits acting chops to years of convincing people he wasn’t driving the boat

• r/canada on Reddit: Kevin O'Leary's wife charged in fatal Muskoka boat crash.

• r/lawcanada - Kevin O’Leary just tossed a toonie to the kids of the mother that he absolutely for sure did not kill7:10 pm - The O'Leary boat arrives at a cottage across the lake

  10:41 pm - The Edwards boat pulls away from their cottage; the lights disappear (start of video to timestamp 1:21)

  11:25 pm - The O'Leary boat leaves the dinner party; Linda appears to be driving

  11:30 pm - Camera from O'Leary cottage depicts collision in the distance (starts at 1:23)