Behind the scenes, Jason Aldean’s relationship with his two oldest daughters is allegedly troubled or even non-existent. Major media outlets seem to be reluctant to report any fallout between Jason and the kids from his first marriage. However, inside sources allege that Jason and his current wife, Brittany Kerr, have been fighting with Jason’s oldest daughter, Keeley Williams, “for years.”
Jason’s second daughter is 17-year-old Kendyl Williams. While some insiders allege that Kendyl is equally unhappy with her dad and stepmom, Jason continues to paint a rosy picture of his relationship with Kendyl.
RELATED: Uncovering Jason Aldean’s Sad Rift with his Daughter
On August 20th, Taste of Country reported that Jason had shared a “touching reflection” about Kendyl around her birthday, and it sounded as sweet as a greeting card. Taste of Country wrote that “hitmaker” Jason had 21-year-old Keeley and Kendyl “before… his two children with Brittany, 6-year-old Memphis, and 5-year-old Navy.” They added that “life is flying by for the singer and his family” and “it’s something [that Jason] is well aware of.”
Jason Is Proud of One of His Daughters
Jason’s critics would throw shade at him for being equally “well aware” of his rumored estrangement with Keeley. He never mentioned Keeley when he celebrated Kendyl in a birthday tribute on Instagram for his 4.5 million followers.
The truth is Jason praised himself on social media before he mentioned Kendyl. He wrote, “As parents, we spend all the young years runnin’ and gunnin’, just trying to keep up and raise good humans.”
When he woke up one day, Jason realized that “they are almost grown.” He thought he “did pretty good at this dad thing.” That’s shocking, considering the unverified but highly suspect rumors that Jason and Brittany have made grown-up Keeley’s life unbearable.
Jason mentioned Kendyl on Instagram when he wrote that he couldn’t believe it’s been “17 years” since she came into the world. He added that Kendyl has “been such a joy” for everyone around her as she’s grown up.
Jason wrote that he was “so proud” of Kendyl and all she stands for. He finished with, “I love u so much and hope u have the best day.”
Jason Stopped Posting About His Eldest Daughter
On Kendyl’s birthday this year, People Magazine updated a report that was “all about” Jason’s four kids. After Jason’s ex-wife, Jessica Ussery gave birth to Kendyl in 2007, Jason often took his first family “on the road with him.” as People described in their article.
A few years ago, Jason posted a throwback photo on Instagram of Kendyl and big sister Keeley. While Keeley has been mysteriously absent from Jason and Brittany’s social media since then, Jason did confess in 2021 that the photo of his two oldest girls was one of his favorite memories of touring when they were little.
Kendyl officially became a teenager four years ago, and People described Jason as a “proud dad” who celebrated her on social media. Jason wished Kendyl a “happy 13th ‘bday’” and called her “one of the coolest and sweetest kids” he knows.
Jason also claimed it was “so cool” watching Kendyl grow up and “turn into the person u are.” He sweetly said, “I love u so much and couldn’t be prouder of you.”
Kendyl celebrated her milestone “sweet 16” birthday in 2023, and Jason went overboard in last year’s birthday tribute on Instagram. Jason described then-16-year-old Kendyl as “one of the sweetest, kindest, and most thoughtful people” he knows. He said it was “truly an honor and a blessing” to be her “daddy.”
Since Jason and Keeley appear to be estranged by then, something about his birthday tribute to Kendyl sounded suspicious. He wrote that “we” are “so proud of the person you are and what you stand for.” Jason finished with, “Don’t ever change that,” with three exclamation marks!!!
Jason and Brittany Spared No Expense for Kendyl’s Party
Country Now reported that Jason and Brittany pulled out “all the stops” for Kendyl’s “lavish… birthday bash.” The real truth is this party sounded hella expensive.
That’s shocking considering that Jason allegedly refused to fund Keeley’s whole college education. According to inside sources, Jason’s alleged stinginess with his oldest child is one of the major reasons behind their fallout.
Country Now called Kendyl’s birthday party “exquisite.” For the record, no one in attendance confirmed that Keeley was a guest at her little sister’s milestone event.
As Country Now reported, Jason and Brittany hosted the party at one of their mansions, and “no detail was missed.” Brittany bragged about Kendyl’s party on social media, mentioning a “braid bar,” a “permanent jewelry bar,” a “customized photo booth,” and “custom illustrations” of the guests.
No one went hungry at this celebration, either. Brittany mentioned the “personal chef” on social media. Country Now wrote that Brittany “recapped the party in an Instagram reel” that featured lines of “custom cookies… and an extravagant cake adorned with colorful roses.”
Brittany and Jason seemed to spend a small fortune on color-coordinating birthday party “flower arrangements” in “various shades of pink and orange.” Thankfully, Kendyl was gracious in thanking her dad and stepmom on social media.
Kendyl Praised Her Dad and Stepmom on Social Media
Country Now confirmed that Kendyl “quickly took to the comments” of Jason’s 16th birthday tribute on social media. She thanked her dad and called Jason a “role model” and “best friend all in one!”
Kendyl also wrote, “Thank you for always making me happy.”
Brittany praised her second stepdaughter on Instagram, wishing Kendyl a “Happy Sweet 16” and calling her “one of the best kiddos in the whole world.” Then, Brittany revealed something that shocked her.
She wrote, “Being [Kendyl’s] bonus mama has been such a blessing.” Brittany could not believe she had been watching Kendyl grow for “a whole decade.” She also acknowledged all the vendors they hired who had made Kendyl’s 16th birthday “extra special.”
Jason and Brittany’s critics might be surprised at how Kendyl reacted to Brittany’s post. Country Now reported that Kendyl “showcased gratitude” for Brittany “in the comments section.”
Kendyl wrote, “Thank you for making this day so special.” Believe it or not, Kendyl finished by writing, “I love you,” to Brittany.
One of Jason’s more playful birthday tributes to Kendyl was posted in 2019, her last year as a preteen. Jason posted a casual-looking photo on Instagram where he’s hugging Kendyl. Jason wished Kendyl a “Happy 12th birthday, ” calling her a “lil baller” and his “Kendyl Bug!”
This all sounds warm and loving, but is it the real truth?
Jason Has No Regrets
People Magazine reported that they interviewed Jason in November 2021, and he opened up a bit more than usual about the struggles of managing his career and raising a family. Jason began optimistically, stating that it felt good “to know that for the past 16 years,” he’d woken up to “a job” that he truly loved to do.
A few years ago, Jason claimed that “if it all went away tomorrow,” he would think to himself, “My kids are good. It’s been great,” and he had “no regrets at all.”
Then, Jason dropped that bombshell. According to People, Jason “shared” that it hadn’t “always been easy balancing his career and his family.”
He told People that he didn’t want to say he’s accomplished “everything” in his life that he “set out to do.” Jason thought he hadn’t done it all, but believed he “accomplished a lot more” than he “thought” he would.
Jason said, “I got four beautiful kids. I got a beautiful wife and had a great career.”
Jason Gave a Nod to Donald Trump
This year, Jason also spoke out again about his extreme political viewpoints. On July 15th, USA Today reported that Jason had “tipped his cowboy hat” to Donald Trump.
This happened after Donald lived through an “assassination attempt” at a campaign rally. Jason was performing a few days later, and he dedicated his “controversial hit “Try That in a Small Town” to Donald.
Someone at Jason’s concert shared a video of the moment, and Jason revealed that “President Trump” is a “friend.” Jason claimed, “We all know what’s going to happen come November, so it’s all good.”
Shockingly, Jason claimed that there’s a lot of stuff in the world. He said, “That’s kind of what this song right here was about.”
Then, he said, “This one goes out to the pres.” Jason was referring to Donald Trump, as there seems to be no stopping the Aldeans and their MAGA love.
