How Naomi Judd’s death has reignited family’s lifelong feud over money

Their story is worthy of a chart-topping country song. Behind their unquestionable fame and fortune, the Judds have been beset by decades of dysfunction – abuse, addiction, and depression. And the tragic suicide of matriarch Naomi, 76, on April 30 – one day before she was due to be inducted into the Country Music Hall of Fame – was the catalyst for more family drama.

This week it emerged that elder daughter Wynonna (pictured right), 58, plans to contest her mother’s will, which made no provision for her or her half-sister Ashley, 54. Instead, Naomi appointed their stepfather, her husband of 33 years, Larry Strickland, as executor of her $25million fortune. 

Strickland (pictured) has no children, but Naomi doubled down on her decision to exclude her own, instructing that, if he were unable, the executorship should pass to his brother, Reginald. Now, DailyMail.com can reveal that Wynonna’s decision to push back at her mother’s wishes is driven by a deep-seated sense of injustice and simmering discord that has plagued the family for decades. According to one well-placed source, ‘With Wynonna, her mother leaving all of her wealth to Larry sticks in her craw. To Wy, her feeling is Naomi built her fortune at least partially on the back of Wynonna’s own hard work.’

The source explained: ‘She was the one who was the lead singer of The Judds dating back to the 1980s and took Naomi from working as a nurse to being a star. ‘Naomi sang harmonies and kind of acted like the ringleader on stage, but it was Wynonna’s amazing voice that pushed them over the top.’ The Judds were the most successful country singers of the 80s, winning five Grammys, nine CMAs and selling 20million records. Pictured: Naomi and Wynonna performing as ‘The Judds’. 

Two weeks before her shock death, Naomi stood on stage with Wynonna in a surprise reunion at the Country Music Awards (pictured). They sang a powerful song of reconciliation, written by Naomi – ‘Love Can Build A Bridge.’ Wishful thinking perhaps. Because if love can build a bridge, then fame and fortune can burn it down. Naomi’s will makes no mention of leaving her share of the duo’s song catalogue to the daughter who sang with her, meaning that whatever portion she owned will go to Strickland – another bitter pill for Wynonna to swallow.

She drew up her will in 2017, ‘being of sound mind and disposing memory,’ but, the source confirmed, ‘Wynonna is still considering her options as far as contesting [it].’ DailyMail.com has also learned that Wynonna’s belief that she is due ‘a piece of the pie’ has pitted her against her A-lister sibling, Ashley, casting their differences into stark relief and bringing old grievances to the fore. Speaking to DailyMail.com, the source revealed that Ashley has sided with Strickland over her mother’s decision.

‘Ashley Judd ( pictured left) has no problem with her late mother Naomi leaving her entire $25million fortune to her second husband Larry Strickland,’ the insider said. ‘With Ashley it’s never really been about the money. She has a net worth of some $14million but lives a relatively simple life.’ In contrast, the source added, the ‘finances are near and dear,’ to Wynonna, who has long had a troubled relationship with money, spending habits, and with her mother whom she called, ‘my beloved enemy.’

It was Wynonna’s fraught relationship with money that, one family source told Radar, lay behind Naomi’s decision to leave her estate in Strickland’s safe hands rather than leave any portion to her older daughter. And, according to the source, Ashley believes that her mother ‘knew what she was doing.’ Another source told DailyMail.com: ‘Wynonna blew through literally tens of millions of dollars she earned with the Judds and as a solo artist.’

That spending was so extreme that in 2000 she was forced to hold a yard sale in her property in Leiper’s Fork, Tennessee in a bid to raise funds. Four years later, still teetering on the brink of bankruptcy, she checked herself into a treatment center to address her ‘money disorder.’ Speaking about her issues, Wynonna once admitted that her early days of poverty with Naomi – a single mother to her girls, living ‘one paycheck from the streets,’ for many years following the end of her first marriage – were hard to reconcile with the wealth of her later life.

She said: ‘I literally went from the outhouse to the White House. I traveled, I took friends, I rented jets. I loved the great rock-star life.’ Today, according to one well-placed source: ‘Wynonna has gotten better at keeping her spending in check, but she’s still not flush as she should be given all the money she’s earned – Ashley is wealthier than her.’ Her hunger for money is also, DailyMail.com has learned, the reason Wynonna made the surprising decision to forge ahead with the previously scheduled farewell tour, The Judds – an 11-date affair that kicks off September 30.

The source said: ‘Wynonna has been out there hustling for years as a solo act, but she plays casinos and small theaters for mostly modest paydays. ‘The Judds are a much bigger draw than Wynonna by herself – this fall tour is playing at good-sized arenas and Wynonna stands to gain a lot better pay than she gets solo.’ The source continued: ‘Of course with Naomi’s death The Judds farewell tour was a solo affair for Wynonna, but she fixed that problem. ‘She called in some favors from some famous friends. So, Trisha Yearwood, Faith Hill and Brandi Carlisle among others are joining Wynonna at various shows to sing Naomi’s harmony parts with Wy as she performs The Judds’ biggest hits.’

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Strickland welcomed Wynonna’s decision when she announced it in May, saying: ‘I am so happy that in this time of grief for us all, Wynonna has agreed to move forward with this tour as my sweet wife, Naomi, would have wanted her to do.’ But in solving one problem Wynonna has caused another, driving a wedge between her and her half-sister. According to one source: ‘Early on, Ashley believed she was going to be part of this Judds farewell tour, to join Wynonna on stage and offer up some remembrances of their mother. But it looks like she has been shut out by Wynonna.’

In fact, in the immediate aftermath of their mother’s death Ashley and Wynonna supported each other in their loss, attending her induction into the Country Music Hall of Fame, May 1, the day after their mother’s suicide. But the sisters’ united front was short-lived. The source said, ‘[At first] Ashley and Wynonna really leaned on each other in their grief over Naomi’s death, but you knew it was only a matter of time before their ages-old sisterly issues would resurface.’ Because behind the seemingly dazzling carousel of celebrity, family life has been anything but harmonious for Naomi, Wynonna and Ashley.

For Naomi’s part she attributed her depression to the sexual abuse she suffered at the hands of an uncle when she was just three. She was 18 when she gave birth to Wynonna on the night of her high school graduation. Speaking many years later she recalled: ‘I got pregnant the first time I had sex. Three months later when I called him to tell him I thought I was pregnant he said, ‘Well, tough luck, kiddo,’ and he hung up the phone and we never heard from him again.’ She had, she said, ‘to marry the town jerk to have a roof and a name.’ That ‘jerk’ was Michael Ciminella who moved Naomi and Wynonna to Los Angeles where Ashley was born three years later.

The marriage ended soon after with Michael abandoning Naomi and her girls (pictured). When she was 22, Naomi was raped and beaten by an ex-boyfriend, a trauma that saw her flee Los Angeles for rural Kentucky where she lived with her children on welfare while training to become a nurse. Their situation was dire. They lived in a home with no electricity, phone, television or indoor plumbing. Naomi moved to Nashville when she qualified and ultimately became head nurse in an intensive care unit. It was there that she learned a patient’s father was in the music industry. She made a tape of herself singing with Wynonna, gave it to him and ‘The Judds’ career in music was launched.

But professional success could do nothing to heal the damage already done. Wynonna attributed the weight issues with which she has struggled all her adult life to her discovery, age 7, that she was not Ciminella’s daughter. Ashley countered her sister’s assessment saying, ‘I think not knowing the truth is what messed Wynonna up rather than having found out’ By her own admission Ashley too was ‘messed up’ by her childhood. In 2006 she checked herself into rehab in Texas for emotional issues including depression, isolation and co-dependency in relationships. ‘I needed help,’ she said. ‘I was in so much pain.’

Ashley elaborated on this pain in her 2011 memoir ‘All That Is Bitter and Sweet.’ In it, the Hollywood star described her childhood as chaotic because of her mother’s drama, claiming that she had been sexually abused by a family member but that when she tried to tell her mother she paid no heed. She wrote: ‘There was too much trauma, abandonment, addiction and shame. My mother while she was transforming herself into the country legend Naomi Judd, created an origin myth for the Judds that did not match my reality. She and my sister have been quoted as saying that our family put the ‘fun’ in dysfunction. I wondered: Who, exactly, was having all the fun? What was I missing?’ Perhaps it wasn’t surprising that, given her own introduction to it, Naomi struggled with motherhood.

Age 49 she gave an interview in which she addressed the subject saying, ‘It’s agony and ecstasy. There’s no question that the mother-daughter relationship is the most complex on earth. It’s even more complicated than the man-woman thing.’ Ciminella once admitted, ‘When the three of them walk into a room they can soak up all the oxygen,’ referring to Ashley, Wynonna and Naomi. According to Ashley her mother would ‘play favorites’ with her daughters. For many years, she has claimed, she felt like ‘the forgotten Judd child,’ left in the care of relatives while Naomi and Wynonna were out playing as many as 200 shows a year. Then in 1990 The Judds’ days of touring came to an end when Naomi contracted Hepatitis C, and it was Ashley’s star that was in the ascendant as an A-List Hollywood actress in movies such as Kiss the Girls, Double Jeopardy and Heat.

One source told DailyMail.com, ‘Suddenly it was all Naomi could talk about much to Wynonna’s chagrin.’ The source revealed: ‘Even though they lived on adjoining properties tension got so bad between Naomi and Wynonna that at several junctures they would go months without speaking to one another – at one point, nearly a year. ‘Ashley has also had times when she would go months without talking to her mother.’ Relations between the women were so strained that, when Wynonna married her third husband, musician Cactus Moser, 65, in 2012, she didn’t invite either her mother or sister.

Wynonna’s first marriage to businessman Arch Kelly III lasted two years ending with divorce in 1998 and resulting in two children, son Elijah, 27 and daughter, Grace, 25. Her second marriage to former bodyguard D.R. Roach ended after three years in 2006 when he was arrested for sexually molesting a child. He is now serving a 25-year-prison sentence. When she tied the knot for a third time to Scott ‘Cactus’ Moser it was outside of Ashley and Naomi’s presence, though they could hear the revelry from their nearby homes.

The following year, in 2013, Ashley’s apparently happy eleven-year marriage to Scottish racing driver Dario Franchitti came to a surprising if amicable end. But, far from turning to her older sister for solace, Ashley’s relationship with Wynonna became only more fraught. Never more so than when Wynonna lost temporary custody of her daughter to her. Grace had sought refuge with her aunt after clashing with her mother. In a bizarre turn of events Ashley filed a police report claiming that Wynonna was spying on her after finding a tracking device attached to her Mini Cooper.

Wynonna ultimately admitted that she had simply wanted to know where her daughter was. Meanwhile, while Wynonna once described Grace (pictured) as ‘the strongest woman in Judd ‘herstory,’ Grace was unable to attend her grandmother’s funeral earlier this year because she is in jail. In 2015 she was arrested and charged with promoting meth manufacture. She pleaded guilty to a lesser charge. One year later, she was arrested once more this time as a fugitive from justice in Alabama and her probation was revoked.

Her prison term is due to run until August 2025 and she will be eligible for parole in February 2023. On May 29, one month after her mother’s death, Wynonna wrote an emotional Instagram post in which she spoke of her unbearable grief and her fear that she would never be able to ‘surrender to the truth’ of the way her mother left this life. She wrote about ‘personal healing,’ her sense of being ‘helpless’ and the few things she knew in the face of such despair and drama.

She said she would continue to fight for her faith, herself and her family, to continue to ‘show up & sing.’ And she vowed to ‘break the cycle’ of addiction and dysfunction that has stalked the Judd women and, with Grace’s incarceration, threatens to tumble into yet another generation. With the drama now tearing through her family that promise hangs, unfulfilled, in the air but, according to Wynonna, one thing is certain, ‘This cannot be how The Judds story ends.’