Kristin Cavallari and Jay Cutler’s Messy Split: Everything We Know About Their Divorce

Credit: Mark Humphrey/AP/Shutterstock

Kristin Cavallari and Jay Cutler’s Messy Split: Everything We Know About Their Divorce

More to the story? Kristin Cavallari and Jay Cutler’s divorce may not be as amicable as fans originally thought. Cavallari and Cutler met in 2010 after Giuliana Rancic, who lived in Chicago at the time, introduced the pair. “We balanced each other out nicely, me being very outgoing and Jay more reserved,” Cavallari recalled in her 2016 book, Balancing in Heels. “Jay told me he loved me weeks into our relationship and told me he wanted to marry me after only 2 months. It all happened quickly, but it made sense: He was exactly what I was looking for. I wanted a man, a real man. … Eight months after our meeting came the ring.” The former Hills star and the ex Chicago Bears quarterback tied the knot in June 2013, but their wedding didn’t go off without a hitch. Cavallari briefly called off their engagement in 2011. "At that moment, something wasn't right," she admitted in her book, noting that she didn’t want to be a stay-at-home mother. "A few things needed to change, and I knew the only way Jay would see how serious I was, was if I ended the relationship. … If I stayed at home, I wouldn't be happy. And would probably end up resenting Jay for it." [jwplayer JF3SoTqs] Cavallari and Cutler welcomed their first child, a son named Camden in 2012. Not long after she gave birth to their second boy, Jaxon, in 2014, the twosome welcomed daughter Saylor in 2015. Cutler retired from the NFL in 2017 after 12 seasons. Not long after his last season, Cavallari made the return to reality TV on E!’s Very Cavallari, which documented her fashion line, Uncommon James. The Laguna Beach alum has been very vocal about the roles in their marriage changing after Cutler was done with football. For more hot celebrity news, listen to Us Weekly editors dish on top topics & trends with these clips from the Hot Hollywood Podcast! "It's been interesting. We've really completely shifted roles, so it's just been trying to navigate this new normal,” she told Entertainment Tonight in 2019. "He's been great. I mean, obviously he's here with my three kids today and you know, this is not the first thing he wants to be doing so he's been great and I couldn't do it without him, truly." Cavallari and Cutler called it quits in April 2020 after seven years of marriage and a decade together. Scroll through for everything we know about their split:

Credit: Mark Humphrey/AP/Shutterstock

Kristin Cavallari and Jay Cutler’s Messy Split: Everything We Know About Their Divorce

More to the story? Kristin Cavallari and Jay Cutler’s divorce may not be as amicable as fans originally thought. Cavallari and Cutler met in 2010 after Giuliana Rancic, who lived in Chicago at the time, introduced the pair. “We balanced each other out nicely, me being very outgoing and Jay more reserved,” Cavallari recalled in her 2016 book, Balancing in Heels. “Jay told me he loved me weeks into our relationship and told me he wanted to marry me after only 2 months. It all happened quickly, but it made sense: He was exactly what I was looking for. I wanted a man, a real man. … Eight months after our meeting came the ring.” The former Hills star and the ex Chicago Bears quarterback tied the knot in June 2013, but their wedding didn’t go off without a hitch. Cavallari briefly called off their engagement in 2011. "At that moment, something wasn't right," she admitted in her book, noting that she didn’t want to be a stay-at-home mother. "A few things needed to change, and I knew the only way Jay would see how serious I was, was if I ended the relationship. … If I stayed at home, I wouldn't be happy. And would probably end up resenting Jay for it." [jwplayer JF3SoTqs] Cavallari and Cutler welcomed their first child, a son named Camden in 2012. Not long after she gave birth to their second boy, Jaxon, in 2014, the twosome welcomed daughter Saylor in 2015. Cutler retired from the NFL in 2017 after 12 seasons. Not long after his last season, Cavallari made the return to reality TV on E!’s Very Cavallari, which documented her fashion line, Uncommon James. The Laguna Beach alum has been very vocal about the roles in their marriage changing after Cutler was done with football. For more hot celebrity news, listen to Us Weekly editors dish on top topics & trends with these clips from the Hot Hollywood Podcast! "It's been interesting. We've really completely shifted roles, so it's just been trying to navigate this new normal,” she told Entertainment Tonight in 2019. "He's been great. I mean, obviously he's here with my three kids today and you know, this is not the first thing he wants to be doing so he's been great and I couldn't do it without him, truly." Cavallari and Cutler called it quits in April 2020 after seven years of marriage and a decade together. Scroll through for everything we know about their split:

Credit: Jake Giles Netter/E! Entertainment

The Signs on ‘Very Cavallari’

While their marriage wasn’t the focus of Cavallari’s E! series, there were certainly signs that they weren’t on the same page on the show.

"Jay has been great, yes. From the outside, things are so perfect and things are so great,” Cavallari said on an April 2019 episode. "But actually, they're not. And that sucks. It sucks. That's the thing, though, with marriage … It's ups and downs.”

She added that their “whole relationship” has had highs and lows.

"Jay and I have problems … I've always been very vocal about that,” Cavallari explained. “We have to work at our relationship, so hearing him say that we're perfect is kind of silly to me. We definitely have issues."

Credit: Courtesy Kelly Henderson/Instagram

Drama With Kelly

Cutler was front and center during season 3 of Very Cavallari after the Uncommon James designer revealed during the premiere that there were rumors that he was unfaithful with her former best friend Kelly Henderson. On the show, however, Cavallari made it clear she didn’t believe the rumors and was more upset with how Henderson handled the situation.  

“When season 2 was airing, there was a lot of talk on social media about Jay and Kelly having an affair,” Cavallari explained on the January 2020 premiere. “Not for one second have I ever thought that it was true. It wasn’t the actual accusations of them having an affair that made me upset, it was how Kelly went about it.”

Cavallari added that she thinks the celebrity stylist was using her for fame.

“The whole time, her whole thing has been like, ‘I don’t care about the show. I only care about your friendship,’” Cavallari told the cameras. “She drank the Kool-Aid, big time. I thought Kelly was the last person on the planet that this would ever happen with.”

In May 2020, Henderson spoke out, denying any type of affair with Cutler. "I have nothing to do with their divorce and I am not dating Jay Cutler,” she said on the "All’s Fair” podcast.

Credit: Courtesy of Justin Anderson/Instagram

Quarantine in the Bahamas

Cavallari and Cutler spent three weeks in the Bahamas with her best friend Justin Anderson and fiancé Austin “Scoot” Rhodes in March 2020. While the vacation wasn’t supposed to last that long, the coronavirus pandemic kept the two couples and Cavallari and Cutler’s kids on the island. While Cavallari and Anderson shared several snaps from the trip, the Hills alum didn’t share any solo pics with Cutler.

“Being stuck on an empty island and forced to quarantine could be worse. thankful for my wolf pack during these scary times,” Anderson captioned a group photo on March 27. “This is where we are, this is us staying positive. we couldn’t be social here if we tried ✌🏼 i am afraid of what we will go home to when they let us back into the states 😢 hope you’re all staying safe where ever you happen to be ♥️.”

Cavallari confirmed on April 7 that they made it back to Nashville.

Credit: Jim Smeal/BEI/Shutterstock

Growing Apart

According to an insider, the twosome “fell out of love and grew apart.” The source added that both parties plan to stay in Nashville to coparent their kids.

Credit: Shutterstock; Inset: MEGA

The Accusations

While the twosome’s split seemed amicable, Cavallari accused Cutler of “inappropriate marital conduct” in her divorce filing in April 2020. She also cited “irreconcilable differences” as the reason for the split.

“[Cutler] is guilty of such inappropriate marital conduct as renders further cohabitation unsafe and improper,” Cavallari claimed in the paperwork.

Credit: Mark Humphrey/AP/Shutterstock

The Announcement

The pair shared the same statement via Instagram on April 26: “With great sadness, after 10 years together we have come to a loving conclusion to get a divorce. We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of. This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family.”

Credit: Jen Lowery / MEGA

The Custody

While the former NFL star asked for joint custody of their three children, Cavallari is seeking  primary physical custody. In her filing, she also denied that Cutler “has always been the available at-home parent and primary caretaker” of their kids.

Additionally, the reality TV personality is asking for the athlete to pay for their kids’ health insurance and other related expenses, including dental, orthodontic and eye care.

Us confirmed in May 2020 that the duo agreed to split time with their two sons and daughter down the middle, with 182.5 days a year dedicated to each parent. As a result, Cavallari and Cutler will divide holidays by odd and even years. While he agreed to pay for their kids’ health insurance and other related expenses, including dental, orthodontic and eye care, neither party is seeking child support.

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The Date of Separation

According to the court docs obtained by Us, Cutler listed their date of separation as April 21. Cavallari, however, declared they were done on April 7 — right after they returned to Nashville from the Bahamas — on her counter-complaint.

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The Animosity

“The word around Nashville is they really just don’t like each other anymore,” a source told Us in April 2020. “They would accuse each other of cheating, but nothing really solid. They are both very stubborn and bump heads a lot and neither backs down.”

The insider added that their relationship became “antagonistic” by the end. "Kristin and Jay always seemed annoyed with each other and they were only on the same side when it came to their kids,” the source said. “It was better for their whole family to divorce.”

Credit: Jen Lowery/MEGA

The In-Laws

After the split news broke, a source told Us that Cavallari did not get along with Cutler’s parents, Jack and Sandy Cutler. “They didn’t gel from the get-go,” the source said. 

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House Hiccups

According to court papers obtained by Us on April 29, the reality TV star started searching for a new place to live five months before her split from the former quarterback. As of November 2019, “things were so bad in the marriage” that Cavallari signed a contract for a new property, which according to the docs, Cutler “never objected to.”

Despite finding a house to move into for her and the three kids, the Laguna Beach alum decided not to buy it and instead “attempted to salvage the marriage.” Shortly after the decision, the couple “realized that attempt to reconcile was not working and knew a divorce was inevitable.”

Days after announcing their split, Cavallari claimed in court papers that Cutler was refusing to release funds for her to buy a new home and was “punishing” her for refusing to agree to his plans for custody of their kids.

In May 2020, Cavallari was able to move forward with her purchase of the $5.5 million home in Franklin, Tennessee.

Credit: Cindy Barrymore/Shutterstock

The Tension

In her divorce filing, Cavallari claimed that Cutler “makes inappropriate statements to and about [her] and attempts to draw her into an argument in front of their minor children.” As a result, Cavallari worries their drama will “escalate” if she doesn’t move out of their shared home.

“Wife does not believe that it is in the best interest of either party or their minor children to reside in the same household,” the docs state. “Wife fears that if the parties are required to remain in the same residence, it would be an unhealthy environment, causing irreparable harm to their minor children.”

Credit: Shutterstock

More Money Woes

“Kristin always knew that Jay was trying to keep some of his money from her,” an insider claimed to Us. “She suspected this for a while and found some type of proof.”

Credit: Courtesy of Kristin Cavallari/Instagram

His Temper

According to an insider, Cutler’s temper played a role in their split.

“There have been instances while filming [Very Cavallari] where he would be mean to her, embarrass her, make her feel bad or storm off. He was never pleasant to the crew or others filming,” the source said. “Her breaking point was this last year. She felt like it was time. They had been trying to make it work and she certainly had been. They had been to counseling.”

The source added that he’s a “shouter.”

“He didn’t have an issue about calling her out or yelling at her in front of other people. That experience was really embarrassing her,” the insider explained. “He would be rude to fans and that was really embarrassing to her. That’s not her at all; she’s always nice to her fans. It’s been like that for a long time, but she was sticking it out for the kids.”

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The Living Arrangements

An insider told Us in May 2020 that the former couple is splitting up time at their main residence in Nashville. “Kristin stays at the house three days then Jay stays at the house for three days,” the source said. “They are three days in the house on, three days off. Then she goes to a friend’s, or he goes to the Bancroft house.”

Cavallari, however, doesn’t like spending time at their former property — the Bancroft house — which they have tried to sell in the past. “She doesn’t feel safe at the Bancroft house because it doesn’t have phone or internet,” the source said. 

Credit: AP/Shutterstock; NINA PROMMER/EPA-EFE/Shutterstock

Jay’s Side of the Story

According to court documents obtained by TMZ, Cutler believes Cavallari buying another home would be “completely frivolous and unnecessary expense” as they already own several properties in Tennessee.

Credit: Courtesy of Kristin Cavallari/Instagram

The Latest

While Cavallari and Cutler worked out their issues legally, a source told Us in May 2020 that things between them had “not improved.”

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His Step Back From Work

After reports surfaced in May 2020 that Cavallari split from Cutler largely because of his unwillingness to work following his retirement from the NFL, a source told Us that there was “no truth” to the rumors. “Kristin never had a problem with him retiring. She didn’t find him unmotivated or lazy,” the insider said. “He took the Miami Dolphins job because it was a lot of money and way more money than sports broadcasting. Why would he not take that? She never criticized him about not working or not working hard enough. She didn’t care.”

Credit: Jake Giles Netter/E! Entertainment

The End of ‘Very Cavallari’

Cavallari announced in May 2020 that her E! series wasn’t returning for season 4. According to a source, she made the decision to “pull the plug” because she didn’t want to discuss the divorce on TV.

“Kristin couldn't do a reality show without addressing the divorce and she doesn't want this to unfold on camera,” the source said. “It's not what she wants to go through.”

Credit: Richard Shotwell/Invision/AP/Shutterstock

Getting Priorities in Check

Cavallari opened up to Us exclusively about what she’s focusing on following the split. “This is the first time in a very long time that I feel like I can take a breath. I’m enjoying things slowed down and having more time to focus on what really matters in life,” she said. “I want to take this extra time I have right now to better myself and be the best mom I can be and continue to grow Uncommon James.” 

She continued, “I’m not thinking about what I want to be doing next year or the year after that. I’ve driven myself crazy with that mentality the past few years. Right now, I just want to be present and enjoy this journey.”

Credit: Courtesy Kristin Cavallari/Instagram (3)

Pushing Through

On August 25, Cavallari debuted two tattoos she got after the split. One of the designs featured a sleek version of her three children’s initials, while the other was a small and elegant butterfly. “Butterflies have been such a sign for me when going through difficult times,” she shared in an Instagram Story update.

Credit: Jim Smeal/BEI/Shutterstock

The Build-Up

The cookbook author told People on September 23 what led to the demise of her relationship with Cutler. “It didn’t happen overnight,” she explained. “We tried really, really hard for years and years. It was the hardest decision I’ve ever made. … I still care so much about him and talk to him almost every day.”

Cavallari said that the choice to end their marriage “wore on” her daily, adding: “A year ago, I felt like I was drowning. I’m proud for making this decision. … I feel like my whole world is opening up now because of it, and I’m just feeling the best I’ve felt in a really long time.”

Credit: Courtesy of Kristin Cavallari/Instagram

The Hard Truth

"It was not an easy decision, obviously," Cavallari told Entertainment Tonight in an interview in September 2020. "It was something that I truly thought about every single day for over two years. It was the hardest decision that I have ever made. But I don't know, my mom used to say, 'You'll know when it's time.' I feel like that was true. I knew. And that's that."

Credit: Courtesy of Jay Cutler/Instagram

Uncommon James

In May 2021, Us Weekly confirmed that the athlete is fighting for half of Uncommon James, Cavallari's business. According to TMZ, she does not agree since she funded the brand with her own money.

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Brief Reconciliation

“Jay and I actually went on a couple of dates, like, months and months and months ago,” Cavallari said during an October 2021 appearance on the “Off the Vine” podcast. “But then I was, like, it’s not there for me anymore.”

She confirmed that the two had since parted ways for good added: “The thing with Jay is, we aren’t getting our divorce because of love lost, which made it really challenging because we were crazy about each other. And so I just decided I didn’t want to be in a toxic relationship anymore and I had to break it off. But then going back and dating him a little bit made me reaffirm it, like, ‘No, I know that I’m doing the right decision.’”

Credit: Shutterstock (2)

Party Time?

“When the settlement came through, I threw a party,” Cutler said on a June 2022 episode of his “Uncut” podcast. He added: “I don’t recommend divorce for anybody. I’m just gonna go ahead and say that, but, um, it worked out. It worked out for Kristin. It worked out for me, so it is what it is.”

Cavallari, for her part, told TMZ later that month that she was not “going to comment” on the pair’s legal status, with Us confirming on June 1 that their divorce was not finalized. The Laguna Beach alum responded to Cutler’s previous comments, joking to TMZ, “I’ve been partying for two years straight.”