Inside the rise and fall of Jay Cutler after former NFL quarterback was arrested for DUI and gun possession

Jay Cutler’s arrest for drunken driving and gun possession on Friday is just the latest chapter in the former NFL quarterback’s dramatic life, both on and off the field.

Cutler, 41, was jailed Thursday after he was pulled over while allegedly driving drunk with two firearms (including a loaded handgun) according to a police report seen by DailyMail.com.

But from his up-and-down playing career – most of which he spent with the Chicago Bears – to his high-profile divorce from Kristin Cavallari, it’s far from the first time Cutler has made headlines.

Beginning his playing career, Cutler entered the NFL as an extremely hyped talent after being drafted No. 11 overall by the Broncos in 2006.

The young passer had some success in Denver after taking over the starting quarterback job — he was even named to his first and last Pro Bowl in 2008.

Former QB Cutler can be seen in 2019 with his ex-wife Kristin Cavallari. They divorced a year later.

But he and newly hired head coach Josh McDaniels didn’t see eye to eye as McDaniels wanted to land Patriots passer Matt Cassel.

“…He basically told me he came to Denver because he wanted to coach me and that we had to trust each other,” Cutler said. ESPN at the time in a rather explosive interview. ‘He has never been critical of me. But trust now? How can I trust him now?’

From there it was on to the Bears, where the gun-toting Cutler gained a reputation for his sometimes apathetic personality and penchant for throwing interceptions.

There was success too, as he threw 154 touchdowns over eight seasons with the team and compiled a record of exactly .500 at 51-51.

But perhaps the most memorable moment from his time in Chicago came in the NFC Championship Game, when he left the game with a knee injury.

It was later revealed that Cutler had a sprained MCL, but the passer’s toughness was widely questioned by fans and even his fellow players after Chicago’s loss to Green Bay in 2011.

Jay Cutler spent eight years with the Bears and threw 154 touchdowns for the franchise

But some remember him most for being in the 2011 NFC Championship Game

Two years later, Cutler and Cavallari married.

The couple first met in 2010 and were together until 2020, where they welcomed sons Camden and Jaxon and daughter Saylor.

However, after nearly a decade together, they divorced, with former “The Hills” star Cavallari saying in a filing that Cutler was “guilty of such inappropriate marital conduct that makes continued cohabitation unsafe and inappropriate.”

And that wouldn’t be the end of the drama in Cutler’s personal life.

By 2022, Weekly contact reported that Cutler was caught on a family vacation with his close friend’s wife.

The publication reported that Cavallari was informed by the husband, who “confronted” Cutler about the affair.

Cutler has since moved on with girlfriend Samantha Robertson, who he has been dating for more than a year, while Cavallari, 37, recently ended a relationship with much younger Mark Estes.

The 24-year-old TikToker and Cavallari dated for seven months, but the influencer clearly made quite an impression on her, as she said on her ‘Let’s Be Honest’ podcast that he was the “best sex” she’d ever had.

“I’ve let go of all that and I think I’m more physically present during sex than ever before,” she said. “And I’m so attracted to you. And I just think we’re having really hot sex.”

Cutler has moved on from his divorce with new girlfriend Samantha Robertson

Kristin, meanwhile, dated 24-year-old TikToker Mark Estes for seven months before they broke up

That relationship has now ended, while the nature of her co-parenting agreement with Cutler has also changed.

Earlier this month, she said again on her podcast that her custody agreement with Cutler had changed over the past year.

‘I am very happy and very satisfied that my life now revolves around my children and work. Happiness to me is peace, and peace to me means making this house exactly how I want it. I’m a homebody – I really am,” she said on her podcast.

She did not provide reasons for why the custody agreement changed, but Cutler’s arrest — which followed a minor traffic accident in downtown Franklin, Tennessee — certainly won’t help any efforts to re-expand his custody.

He was released from the Williamson County Jail later Thursday after posting $5,000 bail.