Reality TV star Kristin Cavallari and former NFL quarterback Jay Cutler have always had a rollercoaster relationship. But the pair appear to have reached the point of no return after announcing their divorce a decade after they first met. And according to the gossip pages, there’s more to their split than meets the eye.
Things initially seemed to be amicable between the couple, though. They announced their split with a joint statement, posted on their respective Instagram pages, that began, “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,” Cutler and Cavallari added. “We ask everyone to respect our privacy as we navigate this difficult time within our family.” The statement was accompanied by photos of the pair in happier times. So, how did things reach such a stage?
Well, it’s fair to say that both parties come from different worlds. Cavallari entered the limelight due to her appearances on Laguna Beach: The Real Orange County. She later became a regular face on another reality show when she joined MTV phenomenon The Hills. Cavallari subsequently added Dancing with the Stars to her resume, on which she danced with Mark Ballas.
Cavallari has also pursued an acting career, showing up on the likes of CSI: NY, Veronica Mars and Adventures in Hollyhood. Moreover, on the big screen she’s appeared in horror Fingerprints, indie movie Green Flash and comedies Spring Breakdown, Wild Cherry and National Lampoon’s Van Wilder: Freshman Year. Then, in 2018 she returned to the reality TV genre with her show Very Cavallari.
The E! series gave viewers an insight into Cavallari’s life with husband Jay Cutler, a former NFL star. The footballer began his sporting career representing Vanderbilt College before the Denver Broncos selected him as a first-round pick in 2006. Cutler enjoyed a few seasons in Colorado and then moved to the Chicago Bears.
Cutler spent close to a decade with the Bears before announcing his retirement from the game in May 2017. He planned to focus upon forging a TV career with Fox’s sports channels. However, the lure of the football field proved to be too strong and he soon came back for another 15 games, this time with the Miami Dolphins. He then hung up his boots for good in December of that same year.
So, how did Cutler and Cavallari’s worlds collide? Well, apparently the footballer initially did all the running. “I got a call from my publicist that Jay wanted to fly me out to Chicago and take me out,” Cavallari told the A Drink With podcast in 2013. “I didn’t know who he was! I had to Google him. I was in the middle of filming The Hills, so I was like, ‘I don’t want a boyfriend in Chicago’ and passed on it.”
However, destiny eventually helped to draw the couple together. “A year later, I was here visiting my mom,” Cavallari explained. “And we ended up going to a preseason game. I had forgotten all about it, and my mom said, ‘Didn’t Jay Cutler ask you out?’ Long story short: I ended up meeting him, and when he walked in, I was like, ‘Oh my goodness!’ I thought he was really cute.”
Cavallari and Cutler had their public debut as a couple in the spring of 2011 when they attended a gala screening of Jake Gyllenhaal flick Source Code. And despite having waited a while to go on a date together, the pair didn’t waste any more time in taking their relationship to the next stage. Indeed, a mere month after gracing the red carpet, they announced they were engaged.
Unfortunately, though, in a sign of things to come, Cutler called off the wedding just three months later. Cavallari was reportedly left devastated by this development. But in November 2011 she was all smiles again after Cutler proposed for a second time, even if it wasn’t done in the most romantic of ways.
“I was in the airport, leaving Chicago,” Cavallari told E! News in 2013. “We had just spent however many days together, and we were texting and somehow it came up, like, ‘Oh, shall we get married?’ We’re like, ‘Yeah, okay.’ And then he sent my ring in the mail. So I actually had my ring sitting at home for a couple of weeks before I put it on.”
The couple once again postponed their nuptials early in 2012 – only this time the reason was a positive one: Cavallari announced that she was expecting a baby. She informed Celebuzz, “I’m not even looking for a wedding dress right now.” And six months later the reality star gave birth to son Camden Jack Cutler.
Cavallari and Cutler did eventually make it down the aisle in the summer of 2013. And the former explained to People that the wait had been worth it. “The flowers and everything were very simple, but it was very warm and cozy,” she said. “It was all about the lighting and the candles, and the atmosphere was just so warm. It was absolutely perfect.”
Then, in the summer of 2014 the pair became parents for a second time with the arrival of son Jaxon Wyatt. They added to their family unit late in 2015 when they welcomed daughter Saylor James into the world. Cavallari admitted to Cricket’s Circle that the inspiration for her third child’s name came from a dog she once met.
Around that time, Cavallari informed American Babythat she and Cutler still had to work hard on their relationship. “I’m not ashamed to say that Jay and I consistently go to therapy, because it’s been extremely beneficial for our relationship,” she admitted. “For example, when you’re fighting, you should never place blame on your partner by saying ‘You do this’ or ‘You do that.’ You should say how those actions make you feel. It goes a long way.”
The family relocated from Chicago to Nashville in 2017 following Cutler’s retirement from the NHL. Judging by Cavallari’s emotional farewell on Instagram, though, it wasn’t an easy decision. “Not only were all three of my babies born here, it’s where it all began with Jay,” she stated. “It brought me closer to my mom who has become my best friend. I’ve made some amazing girlfriends and I’ve really enjoyed being back here.”
In the summer 2018 the couple decided to mix business with pleasure when they became the stars of E! reality series Very Cavallari. In an interview with People magazine, Cavallari revealed that her husband had enjoyed being able to show new aspects of himself to viewers. She said, “Coming from the football world where people didn’t get his personality, it’s been really nice for me and him [to have fans] appreciate him and see the real side of Jay.”
Unfortunately for the pair, however, the reality show appeared to serve as a catalyst for their break-up. During the second season of Very Cavallari, allegations began floating about that Cutler was sleeping with one of his wife’s dearest pals, Kelly Henderson. Cavallari later addressed such gossip during the following season.
An emotional Cavallari told the cameras, “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.” Indeed, Cavallari revealed that she hadn’t had any contact with her one-time friend for months due to the way Henderson had handled the speculation.
“I kept trying to reach out to her and talk to her about it and tell her how I was feeling,” Cavallari added. “And instead of her just owning her side of it and being like, ‘I’m sorry. Oh my God, that was never my intention,’ or whatever, she kept giving me pushback and would get really defensive. And then she literally just stopped responding to me. That, to me, is such a slap in the face.”
In fact, Cavallari was left so blindsided by Henderson’s behavior that she began to regret opening her life up to the cameras. “[Reality TV] totally messes up friendship, and I know that,” she told viewers. “That’s why I was nervous going into it. But I thought Kelly was the last person who would become affected. I’ve completely lost my friend.”
Interestingly, Cavallari had addressed Henderson’s relationship with her husband in a 2019 episode of her reality show. “I think I have just a couple friends that [Cutler] really loves, and Kelly [Henderson] is one of them,” she sated. Cavallari was sitting alongside Henderson at the time.
Henderson then joined in with the conversation, adding, “Jay and I have known each other forever. We’re friends, too. He gives me hugs, if I hug him first.” However, Cavallari’s one-time pal has remained quiet since all the gossip about an affair began. She did appear to indirectly address the drama, though, with a post on Instagram that read, “Take a deep breath and remember who the **** you are.”
Of course, the gossip machine went further into overdrive just three months later when Cavallari and Cutler announced they were separating. A source nonetheless told People magazine that the talk of an affair had “absolutely nothing to do [with it]… Kristin and Jay had been having problems for a long time. They hadn’t spent much time together in recent months.”
“Kristin and Jay are a lot different,” the source continued. “She has so much on her plate, with her brands and with the show. Jay is not as interested in all of that. She’s so passionate about her work, and they couldn’t relate to each other as much. So it pulled them apart.” However, legal documents that were subsequently leaked to the media painted another picture.
Alongside irreconcilable differences, “marital misconduct” was presented as the main cause of the pair splitting up, according to Entertainment Tonight. In one particular file, Cavallari argues that the former NFL star is “guilty of such inappropriate marital conduct as renders further cohabitation unsafe and improper.” She also states that “any misconduct alleged or implied against her in the complaint for divorce was in response to and/or as a result of misconduct on behalf of the Husband.”
In his own petition for divorce, Cutler didn’t reference any form of misconduct against his wife. He did request joint custody of their three kids, though, and claim that he’s “the available at home parent and primary caretaker of the parties’ minor children.” Perhaps unsurprisingly, Cavallari took umbrage with this particular statement.
Indeed, the reality star quickly hit back by arguing that, in fact, she’s always been the “primary residential parent.” Cavallari also sought primary physical custody of Saylor, Jaxon and Camden as well as financial contributions from her soon-to-be ex-husband. In return, she asked for Cutler to be given visitation rights.
Of course, this information gave the tabloids even more ammunition. “The word around Nashville is they really just don’t like each other anymore,” an anonymous insider reportedly told Us Weekly. “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.”
Another insider also reportedly told Entertainment Tonight that the rift between the pair could soon become even wider. “Kristin filing for primary physical custody upset Jay,” they said. “Kristin has made comments about possibly moving back to L.A., which is also a concern of Jay’s, as home for the family is currently Nashville.”
Relations were made all the more awkward by the fact that the couple were still residing in the same house during the divorce proceedings. “Things are very tense between Jay and Kristin right now,” said an insider, according to E! News. “They are on opposite sides of the house and only communicate in regards to the children’s needs. It’s really a power struggle between the two of them.”
However, according to a report by Page Six, there could be another reason behind the pair’s split. The site alleges that Cavallari filed for divorce as she’d become frustrated with her husband’s lack of ambition and drive. Cutler’s professional duties had apparently dwindled since his second retirement from the NFL in 2017.
At the time Cavallari and Cutler wed in 2013, both parties were flying high in their respective fields. However, with the latter now more content to stay at home looking after the children and various family pets, Cavallari is said to have labeled the former footballer “unmotivated.” An insider told Page Six, “[She] was growing increasingly impatient with him.”
“He was supposed to take this big job at Fox Sports and have a life after football that would get him up off the couch and do something,” the source continued. “Instead, he backed out –this is [three] years ago – and joined the [Miami] Dolphins. That didn’t pan out well, and he was left with no TV gig until she got the show for them.”
The insider added that in stark contrast, Cavallari sees herself as “very polished and put together.” According to other reports, though, the former Chicago Bear is considering reigniting his media duties, with ESPN and CBS both reportedly interested in snapping him up. But for Cavallari, it all seems too little, too late.
Nonetheless, not long earlier Cavallari had paid tribute to how her husband had adapted to being a stay-at-home dad. “It’s been interesting,” she informed Entertainment Tonight in 2019. “We’ve really completely shifted roles, so it’s just been trying to navigate this new normal. 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.”
Whatever their differences as husband and wife, though, Cutler still appears to recognize Cavallari’s attributes as a parent. In May 2020 he uploaded a photo of the reality star and their kids Camden, Jaxon and Saylor to Instagram captioned, “Happy Mother’s Day to all the moms. These three little ones picked a good one.”
However, some people believe that this touching Mother’s Day message was actually written by Cavallari herself. In 2018 the reality star revealed in an Instagram Story that she’s in charge of Cutler’s account. “I think there needs to be a little clarification on Jay’s Instagram” she told followers, according to Cosmopolitan. “It’s not him running it. It’s me. It’s what Jay would have if he had Instagram.”
“This is really gross,” a particularly skeptical fan posted in response to the Mother’s Day caption. “If Jay had Instagram he wouldn’t post this. Tell your media team this post is insensitive and disrespectful to Jay.” Another follower responded, “Kristin, babe. We know you run this account. Happy Mother’s Day though.”