Jackson is a veteran Temple University employee and was an academic adviser to the school's women's basketball team when Constand was the team's director of operations.
Jackson claimed that she had once taken a Temple University road trip with the accuser and that Constand had said that the Cosby rape "didn't happen".
Jackson testified while watching television in a hotel room a story aired about high profile celebrities sexually assaulting women.
Ms Constand said she never reported the assault because her assailant was a "high-profile person" and she knew she could not prove it, Ms Jackson testified.
During direct questioning from Cosby's attorney on Wednesday, Jackson recalled a conversation she had in 2004, in which she said Constand allegedly mused about framing an unnamed celebrity for money. "The defendant admitted to the contact that she said happened", Reape told jurors. "I would get that money". I could quit my job. "And then I stopped, and I went up to bed. I could open up a business".
Cosby paid Constand $3.38 million to settle a civil lawsuit she filed after Pennsylvania prosecutors in 2005 initially declined to charge Cosby for the alleged assault.
Jackson's account was immediately challenged by prosecutors, who suggested she was not on the trip on which she says her conversation with Constand took place.
Prosecutors wound down their case earlier Wednesday, introducing the comedian's explosive testimony about giving quaaludes to women before sex - an old admission that's taken on new significance after a half-dozen women testified that he drugged and violated them.
On Tuesday, Montgomery County Detective James Reape, who has been working on the Cosby investigation since it was reopened in 2015, told jurors he wasn't concerned about inconsistencies the defence played up in Constand's story - such as her early uncertainty over the date of the alleged assault - because Cosby's testimony had filled in numerous blanks. He says their encounter was consensual.
Cosby gave the deposition as part of a lawsuit chief accuser Andrea Constand filed against him.
Jackson's name first went public past year after Cosby's publicist Andrew Wyatt mentioned her as a potential witness during the first trial that ended in a hung jury.
Q: How did (the doctor) know that you didn't plan to use (them)?
"Quaaludes happen to be the drug that kids, young people were using to party with, and there were times when I wanted to have them just in case", Cosby testified, according to the transcript. Cosby, who was deposed in 2005 and 2006 as part of his chief accuser's civil suit, was asked about quaaludes, a 1970s party drug that's been banned in the USA since 1982.
Cosby was asked in the deposition. Defense attorney Kathleen Bliss underscored that most of that testimony pertained to the 1970s, and a police detective acknowledged during cross-examination that authorities didn't find quaaludes in a search of Cosby's home after Constand went to police.
O'Neill said there were "simply no grounds for a mistrial" and that Cosby's lawyers were raising the issue too late.
He told jurors that he met Constand three to fives times during the fall of 2002 and spring 2003.
The expert testimony came on the ninth day of Cosby's retrial on sexual assault charges that could send the "Cosby Show" star to prison for years.
The book contained a highly sanitized version of the encounter, with no sex at all, let alone a rape.
Regan said in a sworn statement to prosecutors that she felt she had a duty to publish the truth.
Q: You gave them to other people?