Adrian Humphreys

July 13, 2021

-National Post


A widely held conspiracy theory that celebrity investor and TV personality Kevin O’Leary was really behind the wheel of the speedboat during a fatal crash on a lake surrounded by luxury cottages seems debunked by new video evidence.

Ever since the terrible collision on Lake Joseph in 2019 — after which Linda O’Leary, wife of the star of the Dragons’ Den and Shark Tank television series and a former candidate for the leadership of the federal Conservative party, was charged with careless operation of a boat — there has been a public pushback against the narrative.

The question lingered even after Linda O’Leary’s ongoing trial began in June and a declaration from court, agreed to by the prosecution and the defence, that she was the operator of the boat that night.

Cynical messages to reporters and frequent social media posts rejected or questioned that judicial finding.

It is partly born of Kevin O’Leary’s public persona — one of swagger, assertiveness, arrogance, calling himself “Mr. Wonderful” — alongside the trope of the playboy millionaire driving a speedboat with women alongside him.

In court on Monday afternoon, a different picture emerged, literally, in the form of previously unseen security video, and descriptively, through testimony.

On the evening of the fatal crash on Aug. 24, 2019, Linda and Kevin O’Leary set out with a family friend, Allison Whiteside, in a sleek speedboat to visit a friend’s lakeside cottage for dinner.

Video surveillance from the cottage of their host captured their arrival at the neighbour’s dock shortly after 7 p.m., with the sun shining brightly.

Behind the wheel of the boat is Linda O’Leary, with her husband and Whiteside in the back. She is seen confidently piloting the boat alongside the dock.

On the dock, their host greets them as Linda O’Leary jumps out of the boat with rope in hand and starts tying up the front of the boat.

She then moves to the rear of the boat and, with the help of her host, attaches the rear stern light, a practice, court heard, she had of making sure the light was ready and working for when it would be needed, later, at night, for their return journey.

A second video, shown from the same camera source, shows the trio leaving. It is night and the image is less clear. A portion shown in court shows Linda O’Leary seeming to again take charge of the boat, climbing in and arranging things.

Technical difficulty forced the remaining video to be unavailable before the day’s end but her lawyer, Brain Greenspan, said he expected it to be shown when a different witness testifies.

Linda O’Leary behind the wheel of the Cobalt speedboat was almost always the case, an unusual witness told court Monday.

Trevor O’Leary, 24, is the son of Kevin and Linda, but was called to testify as a witness by the Crown’s prosecutors. Trevor got his boating licence when he was 11 years old; all his boating knowledge was taught to him by his mother, he said.

Does his father drive the boat much, he was asked?

“Not at all,” said Trevor.

He and his mother were out in that speedboat together countless times over 20 years on Lake Joseph. It was a favourite boat of theirs, and they knew the waters well. He said his mother gave him hands-on lessons on boat safety and operation over many summers.

Earlier in his testimony, Trevor said that at lunch the day of the crash, his mother, father, Whiteside and Trevor’s girlfriend shared a bottle of rosé wine.

Earlier in the day, court heard that after the accident, Linda O’Leary told a police officer she had not been drinking alcohol — even before being asked — and was reluctant to take an alcohol breath test after the crash.

Const. Michelle Ingham, an officer with the Ontario Provincial Police, testified that O’Leary was sometimes hesitant and reluctant to provide information, questioned the accuracy of the officer’s statements on the law and said she felt like she was in trouble but hadn’t done anything wrong.

“I told her that in my opinion her pupils appeared to be dilated. In response,” Ingham testified, “she in turn said to me that my pupils appear dilated to her.”

O’Leary asked her what would happen if she refused to take the test, Ingham said. After being told she would be criminally charged with refusing to provide a breath sample with potential penalties being equivalent to failing a breath test, O’Leary complied, about two hours after the crash.

In the end, the police officer gave herself a breath test to show O’Leary how it is done, court heard.

O’Leary’s test showed a blood alcohol range between 50 and 99 milligrams of alcohol per 100 millilitres of blood, registering a warning level of alcohol content, requiring an immediate three-day licence suspension, court was told.

Ingham said that O’Leary told her the other boat involved in the collision didn’t have any lights on and she didn’t see it. She said she called out to the other boat asking if anyone was hurt but didn’t hear any response before the other boat left the scene.

“Without any prompting or questioning from myself, she continued to speak further and told me that she had not consumed alcohol and again, she kept repeating that she felt as though she had not done anything wrong,” Ingham said.

“I did detect an odour of an alcoholic beverage on her breath.

“The first time she denies and says she doesn’t consume alcohol often, ever. I then formed suspicion and I expressed those suspicions to her and then when I ask her for the second time then she tells me she consumed a vodka-water beverage.”

O’Leary said she had a drink after the collision when someone handed her a drink at the boathouse. She said she didn’t know who it was, but said she knew it wasn’t her husband or Whiteside.

Trevor O’Leary said he did not give his mother a drink.

Earlier in Trevor’s testimony, he said he and several friends were sitting around a fire overlooking the lake at the time of the crash. He said he heard their speedboat returning home as he recognized the sound of its engine and looked up to see its lights moving across the dark lake.

He then heard a “loud slam” and saw his parent’s boat was no longer moving. He then saw another boat, a much larger one, suddenly light up. He said he heard his mother’s voice ask if everyone is OK.

He telephoned his mother, but she didn’t answer, and then he called his father, who answered.

Trevor said he asked what was going on and his father seemed to fear it was his son’s group they had collided with. He said his father asked: “Were you guys out in the water? Was that you?”

He and his friends went down to help their parents into the boathouse.

The trial is expected to hear evidence and submissions until July 22.

Justice Richard Humphrey said he would not be issuing his decision immediately after, rather reserving it to a later date.