The ruling on the ground is: Jay Cutler has had a number of headlines since making it big in the NFL.

Before retiring in 2017, the quarterback was able to play 12 seasons in the league, mainly with the Chicago Bears.

While Cutler earned his spot as one of the 100 greatest Bears players of all time, his personal life has often captivated pop culture fans.

In April 2020, Kristin Cavallari and Cutler announced their divorce after 10 years together. The couple shares three children, Camden, Jaxon and Saylor.

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In the years that followed, the athlete made headlines for his dating life and the women he was spotted with near his hometown of Nashville.

In October 2024, Cutler found himself in some controversy again when he was arrested and booked for a DUI at the Williamson County Jail in Nashville. (He has not commented at the time of publication.)

Keep reading to see more of Cutler’s biggest controversies on and off the football field:

Jay Cutler and Kristin Cavallari’s divorce

The couple presented a united front when they released a joint statement on their divorce via Instagram in April 2020. “We have nothing but love and respect for each other and are deeply grateful for the years shared, the memories made and the children we are privileged to be. proud of it,” said the couple. “This is just the situation where two people grow apart.”

Later that month though The hills alum cited “inappropriate marital behavior” and “irreconcilable differences” as reasons for her divorce. In court documents, she also denied that Cutler was “always the available parent and primary caregiver” of their children. The couple has since finalized their divorce and has been able to co-parent.

Jay Cutler hangs out with Kristin Cavallari’s fired employee Shannon Ford

In November 2020, Cutler raised eyebrows when he was spotted hanging out with Ford, who Cavallari memorably took a shot at. Very Cavallari. While appearing on an episode of the “Not Skinny But Not Fat” podcast in January 2021, Ford explained that there was no malicious intent behind the meeting. “People don’t realize this, but I was with my mother and my grandmother,” she said. “It wasn’t spicy like that.”

When asked about Cutler’s divorce, Ford said, “My opinion is it’s none of my business. There are three small children with parents who are getting divorced and that is sad.”

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Jay Cutler’s affairs with Jana Kramer and Madison LeCroy

After his divorce from Cavallari, Cutler realized that hanging out with girlfriends would lead to romance rumors. The NFL star apparently had a brief romance with Kramer – who said the relationship was never serious or exclusive.

While Kramer and Cavallari appeared in 2009 Spring breakdown together, says a source Us that they have “only met in person a few times at work events” and “they have never been friends.”

As for LeCroy, who reportedly disapproved of Cavallari’s parenting skills after the Uncommon James founder’s December 2020 meeting with her ex-boyfriend Austen Krolshe was also briefly linked to Cutler.

Jay Cutler’s Conflicting COVID-19 Views

In August 2021, Cutler claimed that Uber Eats dropped him from an advertising opportunity because their “visions did not align.” Days earlier, Cutler expressed his interest in running for a school board position in Tennessee’s Williamson County after a temporary mask requirement was approved for the upcoming school year.

“Not this parent,” Cutler wrote at the time via X in an article about mothers and fathers calling for face masks. “I really hope I don’t get cornered by Twitter in the first 24 hours.”

Jay Cutler arrested for driving under the influence

The former NFL player was booked into the Williamson County Jail in Nashville in October 2024 for drunken driving, according to online records viewed by TMZ. The NFL star posted bond several hours later and was released. According to the newspaper, Cutler was also charged with failure to exercise due care, violating the implied consent law and possessing a gun while intoxicated.

In the days leading up to his arrest, images on social media showed Cutler on a deer hunt in a neighboring state.