Jay Cutler’s Ups and Downs Through the Years

Former Chicago Bears quarterback Jay Cutler last played pro football in 2017, but the Pro Bowler hasn’t stayed out of the limelight in retirement.

From his high-profile marriage to Kristin Cavallari to his 2024 DUI arrest, Cutler is one of a handful of athletes who has become a household name beyond the NFL.

Cutler and Cavallari began dating in 2010, early in his Bears career, and got engaged in 2011.

“Jay is a good Midwestern boy; he’s a gentleman,” Cavallari exclusively told Us Weekly ahead of their engagement. “He opens up car doors and he did the laundry today, which I thought is pretty cool, so he’s a good boy. We’re in love!”

The pair split just three months later but eventually reconciled and were married in 2013. The couple share three kids, sons Camden and Jaxon, as well as daughter Saylor.

Cutler and Cavallari separated for good in 2020 and finalized their divorce two years later, with the former QB now engaged to Samantha Robertson.

Keep scrolling for Cutler’s ups and downs over the years.

2006

As the reigning SEC Offensive Player of the Year, Cutler was drafted 11th overall out of Vanderbilt by the Denver Broncos in the 2006 NFL Draft. He signed with the team on an incentive-laden six-year, $48 million contract.

May 2008

After losing 35 pounds the previous season and saying he had “no energy,” Cutler learned he had Type 1 Diabetes. Though he insisted his football career was not in jeopardy, he did say he required daily insulin shots.

“We thought it might be stress and the grind of going through a whole season,” he told NFL.com at the time. “But once I got back here and started working out again, I just wasn’t making any improvement. I wasn’t getting any stronger. I was still losing weight.”

Fall 2008

Cutler’s lone Pro Bowl season came the same year as his diagnosis. Also his final season with the Broncos, he threw for 25 touchdowns, setting franchise records for passing yards, completions and attempts. He was traded to the Bears after the season.

April 2011

Cutler proposed to Cavallari over Easter weekend 2011, with a source telling Us at the time that the Hills alum was “so excited and completely blindsided.”

July 2011

The two broke off their engagement after only three months. Cutler confirmed their short-lived split via Facebook, writing, “Thank you all for the support, but if you talk bad about Kristin I will delete and block you.” They reconciled and were engaged again that November.

2012

Cutler and Cavallari welcomed their first child, son Camden.

2013

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

2014

The former couple welcomed son Jaxon.

2015

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

2020

The pair announced their divorce in a joint statement.

“We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made and the children we are so proud of,” they said. “This is just the situation of two people growing apart.”

Cavallari, however, later cited “inappropriate marital conduct” from Cutler and “irreconcilable differences” as reasons for their split.

They finalized their divorce in 2022.

2021

Cutler claimed Uber Eats dropped him from an ad opportunity after he spoke out against COVID-19 regulations in his Tennessee town’s school district. He added that his “views aren’t aligned” with the company.

“Lost a commercial with Uber eats partnering with the NFL,” he wrote via X at the time. “Was going to film in LA, ‘views aren’t aligned.’ Guess they don’t like future School board members. Frees up my weekend.”

2024

After going Instagram official in September 2023, Cutler and girlfriend Samantha Robertson announced their engagement just over a year later.

2025

Cutler was arrested in Franklin, Tennessee on charges of driving while intoxicated and gun possession while under the influence, after officers responded to an accident involving two vehicles. He refused to take a field sobriety test, while authorities found a rifle and handgun in his car, according to the arrest report.

He later struck a plea deal with prosecutors in which he pleaded guilty to one count of misdemeanor DUI. In August 2025, was sentenced to four days in prison and a $350 fine. He also agreed to attend DUI classes and have his license revoked for a period of time. He will serve one year of probation after his release.