Inside Wynonna Judd's Heartbreaking Family Drama

Country music star Wynonna Judd rose to prominence in the 1980s as one half of mother-daughter act, The Judds. She and her mom Naomi had a string of number one hits in the late '80s and were considered to be among the biggest country stars in the world at the time, though things started to go downhill for Wynonna after The Judds disbanded in 1991. The fiery redhead launched a solo career and managed to stay relevant for a few more years (1994's "Girls With Guitars" peaked at number ten on the charts), but before long she would become known for her dramas away from the music industry rather than her achievements in it.

The Judds have reunited for tours now and again over the years, but Wynonna's relationship with her mother has never been straightforward. Sadly, her relationship with her own daughter has become just as complicated, not to mention what she's been through in her love life. From drugs and abuse to life-changing accidents, let's get inside Wynonna Judd's heartbreaking family drama.

On December 18, 2015, Judd's daughter Grace Pauline Kelley was arrested in the parking lot of a Walgreens store in Nashville. Arrest records obtained by RadarOnline reveal that detectives who had been surveilling the lot approached Kelley's car after noticing that her number plate was dangling from the vehicle by a single screw. Judd's daughter was behind the wheel while a man named Richard Wilcutt was next to her in the passenger side seat, and both had been there for a suspiciously long period of time.

They might have gotten away with what they were doing had it not been for the actions of a concerned citizen. As the pair were being questioned, a vigilant passer-by informed police that a bag had been tossed from the passenger-side window. In it, they found a torn up box of pseudo-ephedrine and a receipt for Coleman fuel, ingredients typically used to make meth. Kelley (Judd's daughter by her first husband Arch Kelley) and Wilcutt were both arrested and charged with promotion of meth manufacture.

Could Kelley and her friend have simply been buying the pseudo-ephedrine (sold in small doses for the treatment of blocked sinuses) for medicinal use? The arresting officers were able to rule this out after they put both of their names into a national database and discovered that they had made "a pattern of psuedo-ephedrine purchases consistent with cooking meth," the Daily Mail reported. Wilcutt had the drug on his person when he was searched, and police used store security cameras to confirm that Kelley had purchased it for him, but in the end Judd's daughter got off lightly — she pleaded guilty to the lesser charge of possession.

This lucky escape really should have been enough to scare Kelley straight, but on November 13, 2016, she was arrested for being a fugitive from justice. The troubled young woman was picked up by authorities in Decatur, Alabama, and her probation was immediately revoked. Her case was reportedly transferred to drug court, but once again she flouted the restrictions put on her. On February 20, 2017, Kelley was again arrested for trying to flee from the law.

Kelley's luck eventually ran out in 2018, when she was sentenced to eight years at West Tennessee State Penitentiary. Judd's tearaway daughter ditched the drug recovery program she had been required to attend in November 2017, and authorities were forced to issue a warrant for her arrest. "The defendant was terminated from the recovery court program on November 21, 2017," a court clerk revealed to RadarOnline. "A warrant for probation violation was issued on November 22, 2017 and served on December 16, 2017."

A Williamson County spokesperson was able to confirm that Kelley's most recent probation was officially revoked on February 8, 2018. "She was sentenced to serve eight years," the rep said. "The meth manufacture, delivery, sale and possession with intent charges run concurrent with charges at Maury County." If she served her full term then Kelley would be 30 years old when she got out (her official release date is August 10, 2025), but court records indicate that she will be eligible for parole on February 4, 2019.

Wynonna Judd may not have been arrested and jailed over drug-related activities, but just like her daughter, she too had a tough time growing up. Her sister Ashley Judd (an activist and actress best known for starring alongside Tommy Lee Jones in 1999's Double Jeopardy) aired the family's dirty laundry in All That is Bitter and Sweet, a tell-all memoir in which she revealed how she and her sister were neglected and mistreated as kids. In fact, Ashley became so depressed that by the time she reached sixth grade she was actually considering suicide.

"My mom and sister have been quoted saying that our family put the 'fun' in dysfunction," she wrote (via People). "I wondered: 'Who, exactly, was having all the fun?'" Ashley had a different father than Wynonna, though her dad Michael Ciminella didn't stick around much longer than Charles Jordan had before him. After Ciminella walked out, Naomi married gospel singer Larry Strickland, but things didn't get much better for the kids upon his arrival. Ashley revealed that their mother Naomi even pulled a gun on Strickland on several occasions. "That was just the way we lived," she said.

Judd followed in her mother's footsteps when it came to music, and the apple didn't fall far from the tree when it came to men, either — both have been through a string of failed relationships. Her marriage to Arch Kelley fell apart in 1998 and the pair went their separate ways, leaving the door open for her bodyguard Dan Roach to make his move. Roach became Judd's second husband and things were good for a while, but things came crashing down when he did the unthinkable. In 2007, he was convicted of attempted aggravated sexual battery against a minor.

"He was out of the house within the hour," Judd told CNN in 2010. "I called him everything I could think of. I had a moment where I let it all fly, and then it was done." She filed for divorce just five days later, though the pain Roach caused would last a lot longer than that. "I trusted him with my life, and I didn't want to stop trusting [people]," she said. "It's a little tough because once burned, forever fears the fire. I didn't want to be hell hath no fury like a woman scorned."

While she refused to go into too much detail about the incident, Judd did reveal that the child in question was known to her and the family. "That's what's so scary, is that it is someone that you know," she said. "There's a trust there. There's a bond." The former country star revealed that the victim was in the process of healing, but she also said that the process was none of her business. "This story is so deep and wide," she said. "There's more to it than I can tell you. Because of the child, I won't speak about it. It's their story [to tell] when they're ready to talk."

Remarkably, Judd went on to explain how she was able to eventually forgive Roach, who was struggling with addiction at the time of his crime. "He's sober, and that's what matters to me now," she said. "[I] haven't forgotten, but I have forgiven, enough that I humanly can. I don't wish him dead or anything like that. I just wish to be one of those people that doesn't spend my life being defined by that."

The fact that Judd's ex-husband attempted to sexually assault a child must have cut her pretty deep considering that she went through a similar ordeal when she was a child herself. She and her mother starred in a short-lived reality TV show called The Judds on Oprah Winfrey's OWN network back in 2011, and during the course of the six-part series both Wynonna and Naomi admitted that they were sexually assaulted in their youth.

"She told me about it when we went on tour, but to see her talk about it in front of the cameras... It was so hard to watch," Judd said about her mother being assaulted (via the Daily Mail). "I wanted them to shut the cameras down." Things got even more complicated when they received a copy of Ashley Judd's memoir, which revealed that she was molested when she was still in second grade. "I'm very protective of her, yet it's between her and Ashley," Judd said. "I just have to figure out a way to deal with the dynamics."

Wynonna and her mother Naomi have always had a love-hate relationship, which their reality show made abundantly clear. The pair actually became more distant during the making of The Judds, as Naomi explained when she sat down for an interview with ABC in 2016. "I love her but there are just times we need a break from each other," Naomi said of her daughter (via Taste of Country). "We're still a little estranged from each other. And that happens with mother, daughters."

The country legend revealed that she struggled with depression after the curtain came down on her music career, but she didn't excuse some of her earlier behavior. Naomi (who was only 17 when she became pregnant with Wynonna) lied to her daughter about the true identity of her biological father for 30 years. "Through the decades, we kind of grew up together and I'm always telling her, 'If I'd known better I would've done better,'" Naomi said. "Wy bore the brunt of all of the mistakes I made and we talk about them. We've been through a lot of therapy together."

It was a case of third time's a charm for Wynonna Judd when it came to marriage, though she nearly lost her third husband not long after they tied the knot. Musician Cactus Moser was in a devastating motorcycle accident just months after marrying Judd in 2012, and their lives were forever changed because of it. Moser had to have his left leg amputated below the knee because of the damage caused by the impact, just one of several serious injuries he suffered during the crash. "His hand was shattered, so he had to struggle to hold a fork," Judd told USA Today. "He was doing physical therapy in bed, not able to take a shower by himself. Our bedroom was turned into a medical facility."

Despite the extent of his injuries, Moser (who plays alongside his wife in five-piece blues and rock band Wynonna and the Big Noise) managed to recover and the couple are now happier than ever. "He's playing more passionately than ever," Judd revealed. "I've seen him overcome so many obstacles. The sight of him using the stairs again for the first time had me in tears." After all she's been through, we're happy to hear that Judd finally managed to find some happiness in the end.