He could get probation to 30 years in prison on Monday, when he is scheduled for sentencing for three sexual assault convictions.
Cosby, 81, is due in Montgomery County Court of Common Pleas on Monday to be sentenced by Judge Steven O'Neill in the drugging and sexual assault of his one-time friend Andrea Constand, a former Temple University administrator, in 2004.
Cosby, who was found guilty in April, is the first celebrity to be convicted since the start of the #MeToo movement, the national reckoning with sexual misconduct that has brought down dozens of powerful men in entertainment, politics and other industries. But given his ability to push for an appeal, and the resources that he has to pay bail and remain far from a correctional facility, it is quite possible that he could live his last days as free as he has since the judge overseeing the proceedings ruled that he may remain confined to his residence leading up to this week's sentencing. Therefore, prosecutors will reportedly ask that Cosby be taken straight from court to prison.
Pennsylvania's sex-offender board has examined Cosby and recommended he be deemed a predator, concluding that he has a mental defect or personality disorder that makes him prone to criminal behavior.
Cosby and his legal team have shown that they want to mitigate the amount of damage being done to his reputation, starting with the classification of him as a "sexually violent predator".
The sentencing hearing, which could extend into Tuesday, could also feature testimony and victim impact statements from women, including Constand, who have accused Cosby of assault.
Prosecutors said they would "present numerous witnesses who will testify that defendant sexually abused them" and argued those "uncharged crimes" were relevant to establishing Cosby's character and as a danger to the community. Convicts typically use the opportunity, before a sentence is handed down, to beg for mercy.
"I really think it's important that he spend some time behind bars", said Lise-Lotte Lublin, who said Cosby assaulted her when she was 23 in 1989. His wife of over 50 years, Camille, was noticeably absent.
Since the April verdicts, Cosby has not been permitted to leave his Pennsylvania home.