Kevin O’Leary’s last-minute ‘confession’ made the Crown case at his wife’s trial, prosecutor says

While most court cases involving regulatory legislation fly under the radar, the just-completed careless boating trial in Parry Sound, Ont., was always destined to attract attention.

A rich, reality TV star who once had prime ministerial ambitions and his wife were involved in a fatal nighttime crash on an Ontario lake dotted with multimillion-dollar cottages and boathouses larger than many homes.

On Thursday, both sides laid out their positions as to why Linda O’Leary, wife of Toronto businessman Kevin O’Leary, is or is not guilty of operating the family ski boat carelessly. It is a non-criminal, Canada Shipping Act charge and she could be subject to a fine up to $10,000.

The backdrop of the case is the kind of setting that draws curious onlookers to cruise Muskoka waterways just to “see how the other side of the world lives,” federal prosecutor Samir Adam observed earlier this week.

On Thursday, he told judge Richard Humphrey the Crown had made out its case in part due to the “confession” of Kevin O’Leary, who testified remotely a day earlier from Los Angeles where he is shooting the 13th season of the TV show “Shark Tank.”

While defence lawyer Brian Greenspan said he called the 67-year-old, one-time Conservative Party leadership hopeful in order to exonerate his wife, Adam said his testimony did the opposite by revealing the couple was not looking out for unlit objects on the water the night of Aug. 24, 2019.

The O’Leary vessel struck a drifting boat, a Super Air Nautique, filled with stargazing passengers. Two seated in the bow died.

That happened because the O’Learys wrongly assumed “that if they didn’t see any lights, there was nothing in their way,” which is in clear contravention of the collision regulations in the Shipping Act, he said.

“If you’re boating in pitch black conditions, you cannot make assumptions of what may or may not be in front of you,” Adam said. And even if the Nautique’s lights were out at the time of the collision, the accused’s driving conduct was still careless, he argued.

“The collision and deaths… are the unfortunate and tragic consequences of Ms. O’Leary’s carelessness.”

The prosecution is also alleging the O’Leary boat was travelling at an excessive speed that night, bolstered by Kevin O’Leary’s testimony that they were driving at “planing” speed, which means the hull of their boat had lifted out of the water, Adam said.

There was also evidence in dockside video surveillance footage that showed the light of the O’Leary boat travelling across the water before the crash. Police estimated the O’Leary’s Cobalt was going anywhere from 24 to 30 miles per hour, consistent with testimony from passengers aboard the Nautique, the prosecutor said.

As well, the impact of the crash was “not a small bump in the night,” said Adam.

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Gary Poltash, 64, from Florida, died at the scene, while Suzanna Brito, 48, from Uxbridge, died a few days later.

Adam also summarized “lies” Linda O’Leary told police that “impact her credibility,” including denials that she consumed any alcohol that day — though she had a glass of wine at lunch, and a weak vodka before dinner. She registered an alert on a police alcohol screening device but told the officer she had only one drink after the crash, triggering a temporary driver’s licence suspension.

She also refused to give “contact details” of the hosts of the dinner party where they had been, obstructing an officer’s efforts to get to the bottom of what happened, he continued.

He told the judge Linda O’Leary’s boating skills — which her husband testified were excellent — are not relevant for the judge to consider and noted cases involving regulatory legislation often give greater weight to public good over individual interests.

“This is about public safety. It is not about Linda O’Leary,” Adam said during a closing that used a PowerPoint demonstration.

The judge had only one question at the end of Adam’s submissions. He wanted to know if Richard Ruh, the operator of the Nautique, was also charged with careless boat operation. Ruh pleaded guilty to failing to display a navigational light.

Adam told the judge he wasn’t involved in the charging decisions.

During his submissions, Greenspan reiterated the defence position that alcohol played no role in what happened and accused the prosecution of “cherry picking and focusing in on what they strangely call Mr. O’Leary’s ‘confession.’”

When Adam, during his cross-examination, asked Kevin O’Leary about his role as a lookout on a boat, and whether he keeps an eye out for unlit objects, “he (Kevin) said you have to consider everything,” Greenspan said.

Greenspan said his client has been the target of a “misguided prosecution,” that the Crown had not produced a “scintilla of evidence” that she operated her vessel in a careless manner, and she should be acquitted.

“The Crown cannot and has not proven beyond a reasonable doubt that Mrs. O’Leary was driving at a careless speed, that alcohol impaired her operation or indeed affected her operation of the Cobalt or that she failed to exercise due care and attention.”

Justice Richard Humphrey said he will return with his decision Sept. 14. A former Sudbury-based regional senior judge with the Ontario Court Justice, Humphrey now sits part-time but told counsel this week that he has been at the courthouse until 9 p.m. each night.

Betsy Powell is a Toronto-based reporter covering crime and courts for the Star. Follow her on Twitter: @powellbetsy

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