Jay Cutler's biggest controversies over the years

The decision on the field is: Jay Cutler has made quite a few headlines since his big success in the NFL.

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

While Cutler has earned his place 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 dated near his hometown of Nashville.

In October 2024, Cutler found himself in controversy again when he was arrested and charged with drunk driving at the Williamson County Jail in Nashville. (He had no comment at the time of publication.)

Read on to learn about Cutler's biggest controversies on and off the football field:

Jay Cutler and Kristin Cavallari's divorce

The couple expressed unity when they released a joint statement about their divorce via Instagram in April 2020. “We have nothing but love and respect for each other and are deeply grateful for the years we spent together, the memories made and the children we are proud to be,” the couple said. “This is simply the situation of two people growing apart.”

Later this month, however The hills Alum cited “inappropriate marital behavior” and “irreconcilable differences” as reasons for their divorce. She also denied in court documents that Cutler was “always the available parent and primary caregiver” of her children at home. The couple has now finalized their divorce and are able to become parents together.

Jay Cutler hangs out with Kristin Cavallari's fired co-worker, Shannon Ford

In November 2020, Cutler raised eyebrows when he hung out with Ford, who Cavallari memorably fired at Very Cavallari. Appearing on a January 2021 episode of the Not Skinny But Not Fat podcast, Ford explained that there was no ill intent in the meeting. “People don’t realize this, but I was with my mom and my grandma,” she said. “It wasn’t that spicy.”

When asked about Cutler's divorce, Ford replied: “My opinion is that it's none of my business. There are three young children whose parents are getting divorced and that’s 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 performed in 2009 Spring collapse together, a source said Us that they “only met in person a few times at professional events” and “were never friends.”

As for LeCroy, who reportedly criticized Cavallari's parenting skills after the Uncommon James founder met with her ex-boyfriend in December 2020 Austen Krollshe was also briefly linked to Cutler.

Jay Cutler's conflicting views on COVID-19

In August 2021, Cutler claimed that Uber Eats excluded him from an advertising opportunity because their “views did not align.” A few days earlier, Cutler expressed 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 on X at the time, with an article about moms and dads demanding masks. “I really hope I don’t get cornered by Twitter in the first 24 hours.”

Jay Cutler arrested for drunk driving

According to online records viewed by TMZ, the former NFL player was booked into the Williamson County Jail in Nashville in October 2024 on drunken driving charges. The NFL star posted bail a few hours later and was released. According to the outlet, Cutler was also charged with failure to exercise due care, violating the implied consent law and possession of a handgun under the influence.

In the days before his arrest, footage on social media showed Cutler on a deer hunt in a neighboring state.