Why Wynonna Judd, Rosie O’Donnell Are Quickly Becoming Friends

The country music singer and the comedian have been repeatedly named in headlines over their troubled children’s legal woes. Their daughters have gained infamy for addiction issues and multiple run-ins with the law, including new charges this year.

Given the similarities of their struggles, a source recently claimed Wynonna Judd and Rosie O’Donnell had found comfort in each other.

According to the source, Wynonna has been struggling because of her daughter, Grace Kelley. They noted she suffered for years because of her child’s troubled lifestyle and numerous arrests.

Grace’s latest run-in with authorities left the mother “worried out of her mind,” especially since she has been tasked with raising her granddaughter Kaliyah. The minor child fell under Wynonna’s care after her daughter was arrested and held in jail without bond.

“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 said about Wynonna’s situation, telling In Touch:

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

The insider shared that Rosie’s situation barely differed from her pal’s, with her daughter Chelsea frequently causing trouble. The latter’s infamy began in August 2015 when she ran away from home.

Like Wynonna’s daughter, Chelsea has struggled with addiction issues and has spent a significant part of her adulthood in and out of custody. However, the source implied that Rosie could handle her daughter’s troubles better than her pal could, saying:

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

“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,” they shared.

Days earlier, The Blast reported that Rosie’s adopted daughter made it home just in time for the holidays after her third arrest in two months. Chelsea regained her freedom thanks to an agreement with prosecutors that allowed her temporary release from custody.

The terms of the agreement stated that Rosie’s daughter would be allowed to leave for a drug addiction treatment program. Chelsea would spend 28 days completing the residential treatment program before returning to the Marinette County Jail.

Additionally, her $7,500 bond would be reinstated per the agreement. Chelsea’s biological mother, Deanna Micoley, would also retrieve her from jail and provide shelter for her until she “physically arrives at residential AODA treatment.”

Rosie’s daughter nearly missed the chance to regain her freedom after her initial request for temporary release was denied.

Chelsea requested a furlough from the $7,500 bail set by a judge in Wisconsin after she was arrested for the third time in two months. Her lawyer argued that she needed the exemption for treatment, noting:

“Counsel has spoken with Ms. O’Donnell about the specific details of the treatment obtained for Ms. O’Donnell and would like to direct the court regarding the specific details of the treatment out of respect for the personal information involved.”

However, the judge denied her petition. Chelsea’s time behind bars began after her November 18 arrest. She was taken into custody after being charged with felony possession of methamphetamine, misdemeanor, resisting an officer, and more.

Earlier this month, The Blast shared that Wynonna’s troubles had increased thanks to her infamous daughter. Grace was arrested in October in Albemarle County after allegedly stealing a van from a Charlottesville church.

The country music singer’s daughter was taken into custody and held without bail at the Albemarle-Charlottesville Regional Jail. Grace’s situation worsened when authorities slammed her with seven additional charges, including three felony counts of grand larceny tied to the alleged theft.

Additionally, Officer Corey Legg of the Albemarle Police obtained a search warrant to review Grace’s medical records and determine if she was under the influence of drugs during the incident. However, no drug-related charges were part of the new charges against Wynonna’s daughter.

Will Wynonna Judd and Rosie O’Donnell be able to find peace amid their daughters’ troubled lives?