Bill Cosby paid nearly $3.4m (£2.4m) in a settlement to a woman now accusing him of sexual harassment, according to a prosecutor.
The actor's retrial opened on Monday, with his defence team expected to focus on one of the accusers' previous conviction.
Andrea Constand claims she was drugged and molested by the TV star at his home in 2004. He says the encounter was consensual.
District Attorney Kevin Steele told the court she had been paid $3.38m (£2.4m), a previously confidential figure, after the civil case closed in 2006.
The judge ruled the amount could be discussed in this case, although it was not in the last, which ended in a hung jury.
Mr Steele said: "This case is about trust. This case is about betrayal and that betrayal leading to the sexual assault of a woman named Andrea Constand.
"She's unconscious. She's out of it.
"She will describe how her body felt during this circumstance. She's jolted during this. She feels herself being violated. And she'll tell you she remembers waking up on this sofa with her clothes dishevelled at 4 o'clock in the morning. This is hours after this starts."
Cosby's lawyers produced documents referencing the criminal past of another, Chelan Lasha. She pleaded guilty in 2007 to making a false report to Arizona law enforcement, which the actor's lawyers said is vital to assessing her credibility.
Ms Lasha is one of five additional women allowed to testify as part of an effort to portray the entertainer as one of Hollywood's biggest predators.
She said she was left immobilised and unable to speak after she was given a pill by Cosby and then assaulted.
She was 17 and he was 48 at the time of the alleged attack in 1986.
Her attorney Gloria Allred said the guilty plea to a 2007 case is irrelevant, and nothing to do with the comedian.
On Cosby's arrival to the court for his retrial, a topless protester launched herself at him, with the names of the accusers painted across her body.
Nicolle Rochelle, who appeared in four episodes of The Cosby Show from 1990 to 1992, was intercepted by police as she jumped over a barricade outside the courthouse in Philadelphia. She was charged with disorderly conduct.
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Cosby, 80, faces three counts of aggravated indecent assault, each punishable by 10 years in prison.
His lawyer, Tom Mesereau, won an acquittal in Michael Jackson's 2005 child molestation case.