Wynonna Judd & Rosie O’Donnell ‘Depending’ on Each Other Amid Daughters Grace & Chelsea Legal Woes

Wynonna Judd and Rosie O’Donnell have been friends for over 30 years, but they’re now finding it necessary to lean on each other as they commiserate over their troubled daughters who continue to give them grief, a source exclusively tells In Touch. 

Wynonna, 60, has been fretting over her wayward daughter, Grace Kelley, for years. The legal consequences for Grace’s behavior have the country star “worried out of her mind,” says the source

The prodigal daughter, 28, was recently sent to jail for the third time this year. This time, she’s looking at seven charges — including three pretty serious counts of grand larceny — for allegedly stealing a church van in Albemarle County, Virginia, on October 27.

This most recent arrest comes after she skipped out on a court hearing in Georgia. According to court docs obtained by In Touch, a judge in the state issued an arrest order on September 12, after Grace failed to appear as ordered to follow up on an August 3 arrest stemming from an incident in June that saw prosecutors officially charge her with three misdemeanors: driving while license suspended, fleeing or attempting to elude a police officer and failure to wear protective gear on a motorcycle.

Before the motorcycle-related pick up, Grace was arrested and charged with soliciting prostitution, indecent exposure and obstructing government operations in April. 

While Grace is now being held in jail without bond, Wynonna is caring for Kaliyah, her granddaughter via Grace, but the Grammy winner is finding it difficult to deal with the non-stop stress from her daughter.

“She’s never been as tough as Rosie is and she’s falling apart as Grace languishes in and out of jail – grand theft larceny being the latest charge,” the source says. 

“For Wynonna, raising a young child, her granddaughter, is a lot harder at her age, too,” the insider adds. Luckily for her, “Rosie has her back and she’s telling Wynonna to hang in there and toughen up.”

The View cohost, 62, has plenty of experience in this arena, as she’s been dealing with her daughter Chelsea’s erratic behavior since she first ran away from home in August 2015. Like Grace, Chelsea, 27, has struggled with addiction issues and has been in and out of jail for most of her adult life.

Chelsea was recently picked up by police on October 11 after they executed a search warrant of her Wisconsin home. They ended up charging her with neglecting a child, possession of methamphetamine, possession of THC and maintaining a drug trafficking place after they found her 11-month-old in the home, in horrifying conditions and surrounded by meth pipes, according to court documents obtained by In Touch. She was released on bond, then rearrested, then bailed out again with an upcoming court appearance in December.

“Rosie has her own grievances with Chelsea, who’s been arrested for the third time, but Rosie’s always been better at tough love,” the source adds. 

“Still, it helps to have someone to unload all these burdens on and Wynonna and Rosie are depending on each other for support and encouragement now more than ever.”