Inside the rise and fall of Jay Cutler after the former NFL quarterback was arrested for drunk driving and weapons possession

Jay Cutler's arrest on drunk driving and weapons charges Friday is just the latest chapter in the former NFL quarterback's dramatic life 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 obtained by DailyMail.com.

However, this is far from the first time Cutler has made headlines, from his checkered playing career – most of which was spent with the Chicago Bears – to his high-profile divorce from Kristin Cavallari.

Early in his playing career, Cutler entered the NFL as a highly hyped talent after being drafted 11th 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 NFL star Jay Cutler was jailed Thursday after he was pulled over while allegedly driving drunk in Franklin

Former QB Cutler is seen with his ex-wife Kristin Cavallari in 2019. A year later they divorced.

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

“…He basically told me that he came to Denver because he wanted to coach me and that we needed to trust each other,” Cutler told ESPN in a pretty explosive interview at the time. “He was never critical of me.” But trust now? How can I trust him now?'

From there it was on to the Bears, where the gunslinger Cutler earned a reputation for his at-times apathetic personality and penchant for intercepting balls.

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

But perhaps the most memorable moment of 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 an MCL sprain, but the passer's toughness was widely questioned by fans and even his teammates after Chicago's loss to Green Bay in 2011.

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

However, he is best remembered by some for sitting out part of the 2011 NFC Championship Game

Two years later, Cutler and Cavallari married.

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

However, after nearly a decade together, they divorced, and former “The Hills” star Cavallari said 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.

In 2022, In Touch Weekly reported that Cutler was caught meeting his close friend's wife during a family vacation.

The publication reported that Cavallari was made aware of it by the husband, who “confronted” Cutler about the affair.

Cutler has since moved on with his girlfriend of over a year, Samantha Robertson, while Cavallari, 37, recently ended a relationship with the 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 podcast Let's Be Honest that he was the “best sex” she's ever had.

“I've put all that behind me and I think I'm more physically present during sex than ever before,” she said. “And I feel so incredibly attracted to you. And I just think we have really hot sex.'

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

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

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

Speaking on her podcast again earlier this month, she said her custody agreement with Cutler had changed over the last year.

“I'm really happy and really content that my life right now is all about my kids and my work.” Happiness to me means peace, and peace to me means making this home exactly how I want it . “I’m a homebody – I really am,” she said on her podcast.

She didn't offer any reasons why the custody agreement was changed, but Cutler's arrest – which followed a minor traffic accident in downtown Franklin, Tennessee – certainly won't help any possible effort to renew his custody.

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