The action against Ron Joyce, who claims he's the victim of a "blatant" extortion attempt, predates an unrelated but similar lawsuit filed earlier this year by another woman, who alleges his son, Steven Joyce, assaulted her aboard his megayacht in Florida in an incident he says was consensual.
In mid-2011, according to previously unreported court documents, the woman, now 34, spent the night at Joyce's home in Burlington, Ont., so she could drive him to a doctor's appointment in Barrie, Ont., the following day — apparently because his helicopter had been grounded.
They went to bed separately and she slept alone in the guestroom, they say.
"At 6 a.m., she awoke to find (Joyce) in her bed naked with his hands down her pyjama bottoms with his fingers inserted into her vagina," her unproven claim states. "(She) screamed repeatedly for the defendant to get off of her."
The Toronto woman says she has audio recordings of conversations with him in which he admits to assaulting her, according to her statement of claim.
The claim filed in May 2013, which seeks $7.5 million in damages, alleges the incident left her suffering anxiety attacks and with severe emotional loss.
The Canadian Press does not name alleged victims of sexual assault without their consent.
While both sides agree they continued a relationship afterward, she says in her suit that he subsequently denied the attack and bad-mouthed her to mutual acquaintances.
Joyce, 84, an Order of Canada honouree and one of the country's richest people, admits going into her room that morning but says it was only to awaken her for his doctor's appointment.
"(She) arose from a deep sleep and immediately started screaming and accusing (Joyce) of improper advances," according to his unproven statement of defence from October 2013.
"He did not touch her inappropriately and did not attempt to penetrate her."
Documents say Joyce, a twice married father of seven who has been divorced for decades, met the woman in 2005 when he was 74 and she 24. They developed a relationship.
"The plaintiff and him engaged in consensual sexual activities but on an 'on-call' type of basis," according to his defence statement.
In any event, he maintains that in May 2013, she tried to blackmail him by threatening a lawsuit if he didn't help her financially.
According to his defence statement, she threatened to damage his reputation and report the alleged attack to the police — who declined to lay criminal charges.
"Details of the alleged attack have been fabricated by the plaintiff in an attempt to extort money from the defendant."
While she says they were a committed couple and even talked marriage, he argues she was "almost delusional" about their relationship and "emotionally troubled."
She was younger than his children and some of his grandchildren but referred to him as her boyfriend or fiance even though he made it clear the relationship was casual, he says. She also asked him for money and he extended her a $150,000 loan at one point, he says in his defence.
Two months after the incident, according to Joyce, her lawyer sent him a draft statement of claim related to the alleged attack. To make the matter disappear, he says, she wanted him to forgive the $150,000 loan and pay off another $50,000 to defray her legal expenses.
He agreed, with no admission of liability, as a way to "assist a troubled friend" and considered the matter settled. For that reason alone, Joyce argues, the courts should throw out the suit.
Neither statement of claim nor defence has been tested in court and any trial is likely months if not years away.