Jay Cutler’s arrest for DUI and gun possession on Friday is but the latest chapter in the former NFL quarterback’s dramatic life on and off the field.
Cutler, 41, was jailed on Thursday after he was stopped while allegedly driving intoxicated with two firearms (including a loaded pistol) according to a police report seen by DailyMail.com.
However, from his up-and-down playing career – mostly spent with the Chicago Bears – to his high-profile divorce from Kristin Cavallari, it’s far from the first time that Cutler has made headlines.
Beginning with 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 – even being named to his first and last Pro Bowl in 2008.
Former NFL star Jay Cutler was jailed on Thursday after he was stopped while allegedly driving intoxicated in Franklin
Former QB Cutler is seen with his ex-wife Kristin Cavallari in 2019. They divorced a year later.
But he and newly-hired head coach Josh McDaniels didn’t see eye-to-eye – as McDaniels wanted to bring in Patriots passer Matt Cassel.
‘…He was basically telling me that he came to Denver because he wanted to coach me and that we needed to trust each other,’ Cutler told ESPN at the time in a fairly explosive interview. ‘He’s never been critical to me. But trust now? How can I trust him now?’
From there, it was onto the Bears, where the gunslinging Cutler grew a reputation for his at-times apathetic personality and penchant for throwing interceptions.
There was success as well, as he threw 154 touchdowns across eight seasons with the team and compiled an exactly .500 record of 51-51.
But perhaps the most memorable moment from his time in Chicago was from the NFC Championship Game, when he exited 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 he is most remembered by some for sitting out part of the 2011 NFC Championship Game
Two years after that, Cutler and Cavallari were married.
The couple initially met in 2010 and were together until 2020, welcoming sons Camden and Jaxon and daughter Saylor.
However, after nearly a decade together, they were divorced, with former ‘The Hills’ star Cavallari saying Cutler was ‘guilty of such inappropriate marital conduct as renders further cohabitation unsafe and improper’ in a filing.
And that would not be the end of the drama in Cutler’s personal life.
In 2022, In Touch Weekly reported that Cutler was caught ‘hooking up’ with his close friend’s wife on a family vacation.
The publication reported that Cavallari was made of the aware by the husband, who ‘confronted’ Cutler about the affair.
Cutler has since moved on with girlfriend Samantha Robertson, whom he’s been dating for over a year, 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 the 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 all of that go and I think I am more present physically during sex than I’ve ever been,’ she said. ‘And, I’m so wildly attracted to you. And, I just think we have 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 split
That relationship has since ended, while the nature of her co-parenting agreement with Cutler has changed as well.
Speaking once again on her podcast earlier this month she said that her custody agreement with Cutler had changed over the last year.
‘I’m really happy and really content having my life right now being about my kids and work. Happiness for me is peace, and peace for me is making this home exactly how I want it. I’m a homebody — I really am,’ she said on her podcast.
She did not give reasons as to why the custody agreement changed but Cutler’s arrest – which followed a minor traffic collision in downtown Franklin, Tennessee – surely won’t help in any potential efforts to re-increase his custody.
He was released from the Williamson County Jail later on Thursday after posting a $5,000 bond.
