A former teammate of Jay Cutler, the one-time Chicago Bears quarterback, recently recounted a rather unusual encounter involving Cutler’s unexpected visit to his home in the early hours. This anecdote offers a glimpse into the intriguing personality of the former NFL player, who has been making headlines for different reasons recently.

Cutler, who was previously married to reality TV star Kristin Cavallari, has faced legal issues in Tennessee, including an arrest and sentencing for DUI. Despite his legal troubles, stories from his football days continue to surface, painting a complex picture of the man behind the quarterback helmet.

On the podcast ‘This Is Football’ hosted by Kevin Clark, ex-Bears lineman Kyle Long shared a moment where Cutler made an unannounced entrance into his home. This story sheds light on the unconventional dynamics within the Bears locker room during his tenure.

Long described his relationship with Cutler as distinctive, noting, “When I joined the team in Chicago, it was evident that the quarterback situation was unlike any other from a social perspective.” He went on to offer his take on Cutler’s personality, suggesting, “Jay seems like he was born in the wrong era. He’s reminiscent of a character like Kevin Costner in ‘Dances with Wolves’—a lone figure who prefers solitude, yet has the capability to throw a football with remarkable velocity and confront defenders head-on.”

Reflecting on a particular memory, Long mentioned a night when they went out drinking, highlighting Cutler’s ability to arrange transportation afterwards. “He made sure we had a car to get back,” Long recalled, hinting at Cutler’s responsible side amid the revelry.

‘And I remember one instance, we went out drinking one night, and he got us a car back, by the way. He got us a car. I think he got himself a car back. 

A former teammate of Jay Cutler revealed an incident when the ex-star broke into his house

Kyle Long said that Cutler entered his apartment around 6:00am after a night out

‘And the next morning, somebody had broken into my house at 6:00 AM, and it was Jay Cutler. He was making sure that I was getting to the workout the next day on time. 

‘And he was like, “We can have fun, but we got to…” He broke into my house with his kid in his arm. It was a soft break in. I probably left the door unlocked. 

‘I woke up and Jay Cutler is in my doorway, and he’s like, “Hey, buddy, just making sure we’re ready to roll.” The guy cared in a different way.’

Last month, police in a Nashville suburb released bodycam footage of Cutler’s DUI arrest which led to a short stint in jail.

The arrest, which happened in October 2024, led to a four-day prison sentence as part of a plea deal the former Chicago Bears quarterback made with prosecutors in Tennessee.

Cutler was arrested in the suburb of Franklin, outside of Nashville – the city where he went to college and where he got married to Cavallari.

In the footage, the 42-year-old Cutler was asked how much alcohol he had consumed after rear-ending a different vehicle.

After Cutler replied ‘none’, an officer advised him not to lie. When asked again, Cutler replied, ‘a little bit’.

Bodycam footage from ex-NFL star Jay Cutler’s October 2024 DUI arrest has been released

Cutler was sentenced to four days in jail, but was released after serving two-and-a-half days

The Pro Bowler refused a field sobriety test, leading to him getting handcuffed and put into the back of a squad car with no resistance. 

Cutler was booked for DUI and for a gun possession charge. After cutting a deal with prosecutors, the weapons charge was dropped and he was sentenced to four days in jail for the misdemeanor DUI.

The former 11th overall pick out of Vanderbilt only ended up serving two-and-a-half days of that brief sentence.

He was also sentenced to a year of unsupervised probation, was ordered to attend a DUI safety class and will pay a fine of $350.

While he has served his criminal sentence, Cutler is still being sued by the driver of the vehicle he hit. 

The plaintiff has claimed he has ‘endured physical and mental suffering and the loss of enjoyment of life’ after the incident.

Cutler was formerly married to reality TV star Kristin Cavallari, but they divorced in 2022 

Cutler and Cavallari divorced in April 2020 after seven years of marriage and three children together – Camden, 13, Jaxon, 11, and Saylor, nine. 

Ever since then, they have continued to exchange shots at each other in a messy public split. In August, Cutler hit out at Cavallari for saying she ‘never got a penny’ after they broke up in 2020.

Asked about her comments while appearing on the Take It Outside podcast, he said: ‘I think it’s reckless. I think it’s borderline slander to insinuate that there was zero dollars split during the marriage that each side got. 

‘It’s insanity and it’s completely false, completely untrue. I hate that I even have to address it, honestly.’