Jay Cutler’s Ups and downs: Life of NFL Stars Over the Years

Former Chicago Bears quarterback Jay Carter The last time he played professional football in 2017, the professional bowlers did not stay away from the attention of everyone when they retired.

From his high-profile marriage to Kristin Cavallari In his 2024 DUI arrest, Cutler is one of a handful of athletes who have become household names outside the NFL.

Cutler and Cavallari began dating early in his bear career and got engaged in 2011.

“Jay is a good Midwest boy; he is a gentleman,” Cavalarari told exclusively US Weekly Before their engagement. “He opened the car door and was doing laundry today, and I thought it was cool, so he was a good boy. We’re in love!”

The two split three months later, but eventually got married and got married in 2013. Couple sharing three childrenCamden and Jaxon’s son and daughter Saylor.

Cutler and Cavalarari split well in 2020 Their divorce was finally confirmed Two years later, the former QB is now with Samantha Robertson.

Keep rolling the ups and downs of Cutler over the years.

2006

As the dominant SEC offensive player of the year, Cutler was ranked 11th from Vanderbilt by the Denver Broncos in the 2006 NFL Draft. He signed a six-year, $48 million incentive with the team.

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May 2008

After losing 35 pounds last season and saying he had “no energy”, Cutler learned that he had type 1 diabetes. Although he insists that his football career is not dangerous, he does say he needs daily insulin shooting.

“We think it could be stress and a whole season trouble,” he told him. NFL.com then. “But once I got back here and worked out again, I just didn’t make any progress. I didn’t get stronger. I’m still losing weight.”

Autumn 2008

Cutler’s Lonely Pro Bowl season was the same year as his diagnosis. He was also his last season with the Broncos, throwing 25 touchdowns to set franchise records for passing yards, finishes and attempts. He was traded to the Bears after the season.

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April 2011

Cutler proposes to Cavallari on Easter weekend 2011 us The Hill Alum was “so excited and totally blind” at the time.

July 2011

The two ruined their engagement in just three months. Cutler confirmed their brief split through Facebook, writing: “Thank you for your support, but if you talk about Christine badly, I’ll delete and stop you.” They settled and got engaged again in November.

2012

Cutler and Cavalarari welcomed their first child son Camden.

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2013

Cutler and Cavallari tied knots at a county clerk’s office in Nashville, Tennessee, and held a church ceremony the next day.

2014

The former couple welcomed their son Jaxon.

2015

Cutler and Cavallari announced the birth of their third child, daughter Saylor.

Related: Who is Samantha Robertston? 5 Things About Jay Cutler’s Girlfriend

Jay Cutler has officially entered her boyfriend era with Samantha Robertson. The former NFL star had a social media relationship through social media a few years after her divorce from Kristin Cavallari in September 2023. Cutler and Cavallari have been together for ten years before announcing their breakup in 2020. They shared three children. Although neither Cutler nor Robertson […]

2020

The two announced their divorce in a joint statement.

“We have no choice but to love and respect for each other and are deeply grateful for the years we shared, the memories and the children we are proud of,” they said. “It’s just a situation where two people are separated.”

However, Cavallari later listed Cutler’s “inappropriate marital behavior” and “irreconciled differences” were the cause of his split.

They completed their divorce in 2022.

2021

Cutler claims Uber Eats freed him from advertising opportunities after he spoke to the Tennessee Town school district against Covid-19 regulations. He added that his “inconsistent views” were with the company.

“Working with Uber Eats with the NFL lost the ad,” he wrote on X at the time. “Planned to shoot in Los Angeles, ‘The view doesn’t fit.’ Guess they don’t like future school board members.”

2024

After taking office as an Instagram official in September 2023, Cutler and his girlfriend Samantha Robertson announced their engagement.

2025

Cutler was arrested in Franklin, Tennessee, for driving in drunkenness and firearms when affected, after officials responded to an accident involving two vehicles. He refused to take a live sobriety test, and authorities found a rifle and a pistol in his car, according to the arrest report.

He later A plea agreement reached with prosecutors He pleaded guilty to one misdemeanor DUI. In August 2025, he was sentenced to four days in prison and a $350 fine. He also agreed to take the DUI course and was revoked for a while. After his release, he will serve one year in prison.