The Tragic Truth About Wynonna Judd's Daughter, Grace Pauline Kelley

Country music sensation Wynonna Judd is best known for her collaborations with her late mother, Naomi Judd. Off-stage, Wynonna has two children with her ex-husband, Arch Kelley III. They welcomed their son, Elijah Kelley, in 1994 and their daughter, Grace Pauline Kelley, in 1996. Wynonna and Arch divorced in 1998, which has the potential to have triggered some of the tragedy that has plagued daughter Grace, who has notoriously been in and out of trouble throughout the years. 

Five years after Wynonna divorced Kelley, she married D.R. Roach, a man who was once her bodyguard. Roach was later arrested on allegations that he sexually assaulted a child, per CBS News. 

Wynonna's tumultuous life may be part of the reason her daughter has rebelled against the system and led such a chaotic lifestyle, as is sometimes the case with children who have celebrity parents. As for Grace, she's been arrested for some serious drug-related offenses and has been in and out of the prison system multiple times over the years. 

Wynonna Judd may have named her daughter Grace Pauline Kelley, but the young woman seems hardly as angelic as Princess Grace Kelly. In 2015, Kelley was busted for delivery, manufacture, possession, and intent to sell meth in Maury County and Williamson County, Tennessee. According to Radar Online, Kelley was first busted in a Walgreens parking lot in Nashville after getting into and out of her car multiple times. Cops reportedly found a plastic bag containing pseudoephedrine and a receipt for "Coleman fuel," ingredients that are typically used to make meth.  

The incident landed Kelley a short stint behind bars and more than $3,000 in fines, according to Radar Online. Kelley was put in a court-ordered drug program when she was sentenced to eight years in prison for violating probation. It turns out Kelley left her drug treatment program before she was actually done with rehab. 

With the pressure of being a celeb's kid, it's no surprise that Kelley's arrest wasn't her first taste of being a bad girl.

As Wynonna Judd's daughter, Grace Pauline Kelley had a chaotic upbringing. Sadly, it's not much of a surprise that Kelley's eight-year prison sentence for meth dealing and possession wasn't her first run-in with trouble. According to Radar Online, Kelley went missing "for several days" when she was on a flight layover on her way home from boarding school. She was just 15 years old at the time. 

Kelley also spent time living with her aunt, Ashley Judd, in 2014, after the younger Judd got custody of Kelley amid rumors that Wynonna was allegedly popping pills and being abusive toward Kelley. The custody battle got bitter at one point and Wynonna was even reported to have placed a GPS tracking system on her sister Ashley's car. At the time, Fox News reported that "Wynonna and Arch's teen daughter may have been the anonymous driver of Ashley's vehicle."

As for what happened next for Kelley, she was released from prison four years early in 2019, but must report to a parole officer until 2024 when her sentence would have been up. But, unfortunately, her troubles only continued to intensify after that.

That wasn't the end of Grace Pauline Kelley's legal dramas. Wynonna Judd's troubled daughter was arrested again in April 2020 for violating her probation in relation to her drug case. The U.S. Sun reported she was then sentenced again to eight years behind bars and initially faced a release date of 2028, though it wasn't revealed exactly what she did to land herself back in hot water.

But Kelley got lucky and 2021 saw her granted parole with an order to complete treatment for her demons, per The U.S. Sun. "The Board reached a final decision on April 22, 2021, recommending releasing her to parole supervision with post-release conditions," a spokesperson for the Tennessee Board of Parole said in a statement. It was confirmed Kelley had agreed to get initial treatment for her drug addiction, aftercare, and submit to random drug tests. She wasn't able to head straight home to celebrate the news though, with the spokesperson explaining, "Her home plan will need to be approved by Tennessee Department of Correction, then a parole certificate will be issued and then Tennessee Department of Corrections will manage her release back to the community."

But it didn't end there, either. In August 2021, Kelley was arrested yet again and debuted a surprising new accessory in her mugshot — a face tattoo! Judd's daughter was arrested on another probation violation, according to The U.S. Sun, and showed off some unique ink above her right eye.

In 2020, Wynonna Judd got candid about her daughter Grace Pauline Kelley's struggles as she's spent much of her life getting into trouble with the law. "I will tell you this. My daughter is the strongest Judd woman in our 'herstory.' She's healthier than I was at 23," Wynonna said of her daughter on Fox Nation's "The Pursuit! with John Rich." "How she got there — I would not go that way, but I was also sequestered," she added. Wynonna then even went as far as to claim that she believes she could have gone the way of her daughter had she not spent so much of her time on the road with her mom, the late Naomi Judd, touring the world as country music duo The Judds.

Sadly, Naomi died tragically by suicide in May 2022, and Kelley's legal issues appear to have stopped her from being able to spend her grandmother's final years with her. The U.S. Sun confirmed Kelley was still behind bars when Naomi died and revealed that she was expecting a baby in March 2022, reportedly with a man who is also incarcerated. Kelley's fellow inmate Florence Fort spoke about her pregnancy with the outlet, revealing Kelley already had a name picked out for her baby. "She would call Wynonna all the time. She talked to her mom a lot. We even gave her a baby shower in jail and her mom called in the middle of it," Fort revealed.