On 24 August 2019, O'Leary and his wife Linda were involved in a fatal crash on Lake Joseph in Muskoka, Ontario when the two were on a boat owned by O'Leary and operated at the time by Linda. Their boat collided with another boat, and a 64-year-old man and 48-year-old woman on the other boat were killed. O'Leary said in a statement that he was cooperating with the police investigation, and that the other boat did not have its lights on and "fled the scene". The police stated that both boats left the scene to "attend a location and both parties called 911." On 24 September, Linda O'Leary was charged with "careless operation of a vessel" under the small vessel regulations of the Canada Shipping Act, a charge that carries a maximum 18 months imprisonment and a $1 million fine. The driver of the other boat, Richard Ruh of Orchard Park, New York, was charged with "failing to exhibit navigation light while underway." On 11 October, the Public Prosecution Service of Canada ruled out any jail time for Linda.