Why Bill Cosby Could Wind Up Behind Bars Again

Bill Cosby has been a free man ever since his 2018 sexual assault conviction was overturned five years ago. But now, new court filings could see him back behind bars – if a judge sees fit.

New documents filed by Debra Motsinger—the woman whom we previously reported filed a civil suit in September 2023 alleging that Cosby drugged and sexually assaulted her in 1972—ask a judge to hold the disgraced actor in contempt for failing to pay out any of the $59.25 million he owes her in her suit.

Motsinger also claims that the former “The Cosby Show” star didn’t turn over any financial documents needed for the judgment, despite the judge in the case ordering him to submit information about his “bank accounts, income and assets” in early October, per TMZ. At the time, Cosby was also ordered to pay $1,560 in sanctions within the next 10 days, but he allegedly didn’t make good on that either.

Related: Bill Cosby Finally Makes This Shocking Admission in Sexual Assault Case!

As a result, Motsinger is hoping that a judge can force him to come back to court so he can explain why he hasn’t handed over any money. If he doesn’t show up, she’s seeking a warrant for his arrest and asking for him to be jailed until he complies with the court’s orders. As noted by Complex, she’s also asking the judge to jail the comedic veteran for five days for each violation and to receive up to $1,000 in fines and an additional $3,284 in attorney’s fees. 

Despite Motsinger’s civil suit win, Cosby maintained his innocence and has yet to respond to these new court filings. His case with her came with horrifying details and surprising admissions. As we told you in January 2026, Cosby admitted during a deposition in this case to regularly and repeatedly refilling a prescription for quaaludes with the intent of giving them to women before or during sexual encounters.

Motsinger claimed that Cosby gave her wine and what she believed was an aspirin in his dressing room, causing her to become ill and drift in and out of consciousness. She alleged that she was then placed in a limousine with Cosby before waking up at home partially undressed and believing she had been drugged and raped.