How Jay Cutler's Life Changed After His Divorce From Kristin Cavallari

Jay Cutler's whirlwind romance with his ex-wife Kristin Cavallari began in 2010. The two met after being introduced by their mutual friend Giuliana Rancic, and went on to get engaged the following year. The pair had a few bumps along the way, breaking up a few months after their engagement and reconciling later that year. Cavallari and Cutler welcomed their first child in 2012, tied the knot in 2013, and went on to welcome two more children together.

Their lives in Nashville were heavily documented on their joint reality series, "Very Cavallari," which debuted in 2018. The show followed the ins and outs of their large family and their work-life balance, with the "Hills" alum managing her jewelry and skincare brand Uncommon James and Cutler juggling his life post-NFL. Ultimately, their love chapter ended in 2020 when the two announced they were filing for divorce. 

A lot has been said in the press about Cutler and Cavallari's former life together, with claims of infidelity and a toxic relationship dominating the media shortly after their split. The former Miami Dolphins backup quarterback seems to have a different view of his relationship with his ex-wife than she does, but it hasn't gotten in the way of their co-parenting relationship. While fans may not have kept up with the NFL player since "Very Cavallari" ended, it doesn't mean he hasn't been busy. So, how has Jay Cutler's life changed after his divorce from Kristin Cavallari?

Jay Cutler and Kristin Cavallari's marriage came to an end in April 2020 when the pair filed for divorce citing "irreconcilable differences." At the time, Cavallari took to Instagram to announce the decision, writing: "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 ... 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."

According to court documents obtained by Entertainment Tonight, the former Chicago Bears quarterback filed for joint custody of their children. His ex-wife petitioned for primary custody. While Jay claimed he was "the available at home parent and primary caretaker of the parties' minor children," the Uncommon James founder rebuked that notion, alleging that she was "a fit and proper person to be named Primary Residential Parent."

The he-said-she-said ultimately came to a close in May 2020, when the former spouses reached a joint custody settlement. Cutler and Cavallari agreed to share their parenting time equally, with each getting an allotted 182.5 days with their kids. As per the "Laguna Beach" star's Glamour interview, that agreement meant that she and Cutler each have one week on and one week off with their children. As for how he managed his new parenting role post-divorce, he told E! News: "It's good. I mean, kids are resilient. With school and all the activities, we've done a good job of putting them first."

Jay Cutler and Kristin Cavallari's split got even messier when rumors swirled that the former NFL player was having an affair. During Season 2 of "Very Cavallari," the rumor mill buzzed with fans claiming Cutler was secretly seeing Cavallari's best friend and stylist Kelly Henderson. The "Hills" alum addressed the accusations during the Season 3 premiere, admitting that the claims led to a falling out between her and her former friend. 

"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," she said (via People), adding that Henderson "kept talking about Jay on social media," and "would get really defensive."

Henderson denied the affair, admitting on the "All's Fair" podcast: "I have nothing to do with their divorce and I am not dating Jay Cutler." Cutler seconded that notion when he was asked about the allegations on the "Sofia With An F" podcast. "Nope, never cheated. Not once," he said when asked if there was any truth to the rumors with Henderson. When asked why he felt their marriage ended, he admitted: "I guess she fell out of love ... or it was toxic, I mean [it] depends on the day I guess." 

There are parties — and then there are divorce parties. Jay Cutler seems to know the difference, as the former NFL quarterback joked on his podcast "Uncut with Jay Cutler" about his divorce ending with a bang. In the 2022 episode, Cutler's friend Clay Travis joked about professional football players going broke after nasty divorces, while Cutler admitted his case gave him cause to celebrate. "I don't know what I can say, first of all," Cutler admitted laughingly. "I don't know if I made money, I just didn't ... [I] did OK." The former Chicago Bears player went on to add that "when the settlement came through, I threw a party."

Cutler (who reportedly made $120 million as an NFL player vs. his ex-wife's reported $30 million) said that in the end, both parties went home happy. "I don't recommend divorce for anybody, let me go ahead and say that," he explained. "But, it worked out. It worked out for Kristin, it worked out for me. It is what it is." As for Cavallari's response to his divorce party, she refused to comment. She did, however, throw some shade at her former beau, telling TMZ: "I've been partying for 2 years straight," apparently referencing their decision to split in 2020.

Following the news of Jay Cutler's divorce from Kristin Cavallari, the couple's reality show "Very Cavallari" also came to an end. The show premiered in 2018 on E! Network and followed their busy lives being parents and entrepreneurs for three seasons. Cavallari announced the news via Instagram, writing: "As I start this new chapter in my life, I have decided not to continue with 'Very Cavallari.' I've absolutely loved my time filming and am so grateful to E! Entertainment for making this journey possible."

While we're not sure whether Cutler was very broken up about it (given his non-emotional attitude toward pretty much everything on the show), fans will have to live without his dry humor and sarcasm. The former NFL player gave viewers an inside look into what his life was like post-retirement on the show, complete with watching his backyard deer cam and grudgingly obliging to help his then-wife with all her Uncommon James duties. He did happen to catch a kitchen towel on fire though, in what can only be described as riveting television. Either way, we're pretty sure Cutler can live without cameras intruding on his day-to-day personal life.

Jay Cutler kept himself busy post-divorce by becoming an entrepreneur. The former NFL player launched his meat subscription service "CUTS" in 2021, partnering up with famous butcher "MEATMEN" star Pat LaFrieda. CUTS offers high-quality meats delivered to a customer's doorstep, with boxes including USDA Prime Center Cut NY Strips, filet mignons, high-end chicken, pork chops, beef burgers, as well as a brisket and beef belly blend. 

Cutler opened up about the business venture to E! News, admitting that it took him a while to find his footing following his NFL retirement. "For me, getting out of football and then taking a little bit of time to figure out exactly what I wanted to get involved with and who I wanted to get involved with was really important to me," he explained, adding, "I wanted to make sure that my next couple ventures were things that I enjoyed doing and could sustain for a long amount of time."

Ultimately, Cutler decided to go back to his Indiana roots and longtime love of great steaks to develop his own company. "Pat is top of the line. His family's been in the business for 100 years. We're doing one-month, three-month and six-month subscriptions. Pat and myself are picking out the products that are getting sent out each month. It's all USDA prime and Pat picks from the top 4 percent of beef in the country."

Jay Cutler and Kristin Cavallari proved the haters wrong when they were able to maintain a friendship following their divorce. Shortly after the former spouses announced their split, Cutler shared a sweet Instagram post honoring his ex-wife (via E! News). "Happy Mother's Day to all the moms," he wrote, alongside a photo of his children at the beach with Cavallari. "These 3 little ones picked a good one."

Cavallari returned the favor by posting an Instagram tribute to her ex-husband the following month on Father's Day. "Saved the best for last ... happy (late) Father's Day to Jay," she wrote on an old photo post of their kids watching Cutler play football (via People). "We had a beautiful day together yesterday at my new house. Modern family? Co-parenting? Whatever you want to call it, we are navigating it the best way we know how. And what I do know is, our 3 kids are lucky to have him as their daddy."

The former couple has put their co-parenting relationship above anything else. In 2021, amidst rumors that the two were on bad terms, they took to Instagram (per People) to post a matching photo together with the caption: "The world is full of users. 10 years. Can't break that." Cavallari opened up about her relationship with Cutler in an interview with Mr. Warburton in 2021, saying, "I always want my kids to see Jay and me as a united front. He's their father. That's important and they need to see that from me."

Jay Cutler had some words for his former wife Kristin Cavallari after she opened a Pandora's box about their marriage to the press. The "Hills" star got candid about her marriage to Cutler on the "Call Her Daddy" podcast, saying that "It was toxic ... period end of story. She also said, "If there's any takeaway from that is you can't ignore red flags people don't change and you gotta trust your gut."

Though Cutler has been quieter in the media regarding their past relationship, he responded to his ex-wife on an episode of the "Sofia With An F" podcast. "If that's the way she feels, I mean [her feelings about the marriage] changed over the course of two and a half years." He went on to call her claims "comical" adding, "Why are we why are we having these conversations in public?"

Cutler admitted that he strays away from commenting on his marriage to Cavallari out of respect for their children. "If she wants to say stuff, she can say stuff. I'm not going to go down that road about her. I mean, she's still the mother of my kids," he admitted. 

Jay Cutler pumped the brakes on getting back on the field after his divorce from Kristin Cavallari. And no, we don't mean the football field. Cutler had reservations about making romantic connections following the split, especially since it had been a decade since he was last single. On the first episode of his podcast "Uncut with Jay Cutler," the former NFL star got candid about dating again, admitting: "It's hard as hell. Finding out what people really really want from you, I think that's probably an issue."

Cutler also said that being a father places added pressure on finding the right person to spend his time with. "I'm at a different phase of my life now you know with kids and priorities [have] just changed." He explained that he had to get accustomed to the new wave of technology, where more and more people are meeting each other online. "The whole landscape has changed," he said. "There's apps, there's Twitter, there's Instagram, like it's a whole different ballgame ... you're not just walking into a restaurant or bar and talking to somebody ... that doesn't exist anymore."

After 12 seasons in the NFL, Jay Cutler finally retired in 2017. But putting behind his football days for good was out of the question for the former quarterback. The "Very Cavallari" star signed a deal with Fox Sports in 2017 to serve as a commentator at NFL games alongside Charles Davis and Kevin Burkhardt. However, he chose to sign with the Miami Dolphins for one more season as a backup quarterback instead of going into commentating.

Now that his days playing on the field are officially over, Cutler is open to more broadcasting opportunities in the future. "I would love to do it. I think it's a fun gig. It keeps you in the game," he admitted to Front Office Sports. "If an opportunity arises, I would jump at it." He went on to add that he turned down opportunities to work as a sports commentator due to wanting to spend more time with his kids. "I was in a period of my life where the kids were young," he explained. "I didn't want to get back into that schedule of Friday-Saturday-Sunday-Monday-gone. But now things have calmed down for me. My kids are a little bit older and in a better place."

Cutler gives plenty of sports opinions on his "Uncut with Jay Cutler" podcast, but he's keeping the sports broadcasting door open. "I could do everything I wanted to do. Color commentary is kind of the last bucket. If I can get that filled, it would be great," he said.

Watch out sports fans — another former pro-athlete is off the market. We're of course talking about Jay Cutler debuting his romance with Samantha Robertson in 2023. Robertson was previously married to Trace Ayala (one of Justin Timberlake's close friends), but the two later split. The brunette beauty took to Instagram to reveal the new relationship, posing next to Cutler in front of a gorgeous sunset and captioning the photo: "Sunsets in Montana never disappoint" alongside a heart hand emoji. The former NFL player commented on the picture, asking, "When are we going back?"

It's the first public relationship Cutler has been involved in since his split from Cavallari in 2020. Robertson also posted a series of Instagram snaps of the two vacationing in France, as well as attending a wedding together. "Vive la France," she wrote. While the pair have remained quiet on their official status, they seem quite cozy with each other on their European getaway. We can only hope this relationship turns out better than his last!