Cosby's attorney Jennifer Bonjean argued Tuesday in the virtual hearing that these witnesses unfairly prejudiced the jury -- and some judges suggested they agreed.
"I tend to agree that this evidence was extraordinarily prejudicial to your client," Justice Max Baer said to Bonjean.
The state Supreme Court is made up of seven members, and at least four sharply questioned Assistant District Attorney Adrienne Jappe, who argued for the prosecution. She argued that the prior bad acts witnesses showed Cosby had a common scheme or plan in his assault. She also said their testimony showed Cosby did not make a mistake or accident in his actions.
However, Justice Kevin M. Dougherty questioned whether the witness accounts, which dated to incidents in the 1980s, were too distant to be appropriate. In addition, Justice Christine Donohue questioned whether the prior bad acts witnesses were too dissimilar from Constand's allegations.
"Frankly, I don't see it," Donohue said.
The sharp questions open the possibility that Cosby's conviction could be overturned on appeal. A ruling on the case is not expected for months.
Deputy District Attorney Robert Falin argued Tuesday that Castor had simply issued a press release declining to prosecute. The press release was not legally binding, he argued, and left open the possibility that future evidence could change his decision.
Indeed, Cosby's attorney admitted Tuesday that Cosby's deposition may have been a mistake.
"In hindsight, we would have preferred to have seen a written agreement," Bonjean said.
In a statement sent through a spokesman, Cosby praised his attorney's arguments in the hearing.
"This was not just an historic day for me, Bill Cosby, but it became a beacon of hope for those countless American Citizens of the Keystone State in Pennsylvania Correctional Facilities, whose constitutional rights might have been grossly abused because they lacked resources and means to fight prosecutorial corruption," he said in a statement.
"I'm so happy because I hope and truly believe that justice will prevail."