Jay Cutler’s arrest for DUI and weapons 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 Thursday after he was stopped while allegedly driving while 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, primarily with the Chicago Bears, to his high-profile divorce from Kristin Cavallari, this is far from Cutler’s first time in the headlines.
Beginning his playing career, Cutler entered the NFL as an extremely hyped talent after being selected 11th overall by the Broncos in 2006.
The young quarterback had some success in Denver after taking over as starting quarterback, even being 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. They divorced a year later.
But he and newly hired head coach Josh McDaniels were at odds, as McDaniels wanted to bring in Patriots quarterback Matt Cassel.
“… He was basically telling me that he came to Denver because he wanted to train me and that we needed to trust each other,” Cutler said. ESPN at that time in a rather explosive interview. “He has never been critical of me. But trust now? How can I trust him now?
From there, he landed on the Bears, where the gunslinging Cutler earned a reputation for his sometimes apathetic personality and penchant for throwing interceptions.
There was success, too, as he threw 154 touchdowns in eight seasons with the team and compiled an exactly .500 record of 51-51.
But perhaps the most memorable moment of his time in Chicago was 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 quarterback’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
But some remember him most for not participating in part of the 2011 NFC Championship Game.
Two years later, Cutler and Cavallari 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 divorced, and former ‘The Hills’ star Cavallari said in a filing that Cutler was ‘guilty of inappropriate marital conduct that makes cohabitation unsafe and inappropriate.’
And that wouldn’t be the end of the drama in Cutler’s personal life.
In 2022, In weekly contact reported that Cutler was caught “hooking up” with his close friend’s wife on a family vacation.
The publication reported that Cavallari found out from the husband, who ‘confronted’ Cutler about the matter.
Cutler has since moved on with his girlfriend Samantha Robertson, who he has 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 a big impression on her, as she said on her ‘Let’s Be Honest’ podcast that he was the ‘best sex’ she’d ever had.
“I let all that go and I think I’m more physically present during sex than ever,” she said. And I feel tremendously attracted to you. And I think we have really hot sex.
Cutler is over his divorce with his new girlfriend Samantha Robertson
Meanwhile, Kristin dated TikToker Mark Estes, 24, for seven months before splitting.
That relationship has since ended, while the nature of her co-parenting agreement with Cutler has also changed.
Speaking once again on her podcast earlier this month, she said her custody agreement with Cutler had changed over the last year.
‘I am very happy and very pleased that my life at the moment is focused on my children and my work. Happiness to me is peace, and peace to me is making this home exactly the way I want it. “I’m a homebody, I really am,” he said on his podcast.
He gave no reason for why the custody agreement changed, but Cutler’s arrest, which came after a minor traffic collision in downtown Franklin, Tennessee, surely won’t help any potential efforts to re-increase his custody.
He was released from the Williamson County Jail later Thursday after posting $5,000 bail.