Jay Cutler’s Biggest Controversies Through the Years

The ruling on the field stands: Jay Cutler has faced some headlines ever since he made it big in the NFL.

Before retiring from football in 2017, the quarterback was able to play 12 seasons in the league, primarily 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 share 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 out and about with near his hometown of Nashville.

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

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 put on a united front when they released a joint statement via Instagram about their divorce in April 2020. “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,” the couple said. “This is just the situation of two people growing apart.”

Later that month, however, The Hills alum cited “inappropriate marital conduct” and “irreconcilable differences” as the reasons for her divorce. In court documents, she also denied that Cutler “has always been the available at-home parent and primary caretaker” of their children. The pair have since finalized their divorce and have been able to coparent.

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 fired on Very Cavallari. While appearing on a January 2021 episode of the “Not Skinny But Not Fat” podcast, Ford explained that there was no ill intention about the meeting. “People don’t realize this, but I was with my mom and my grandma,” she said. “That’s how not spicy it was.”

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

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Jay Cutler’s Flings With Jana Kramer and Madison LeCroy 

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

While Kramer and Cavallari appeared in 2009’s Spring Breakdown together, a source told Us that they “only met a few times in person at events for work” and “they were never friends.”

As for LeCroy, who allegedly slammed Cavallari’s parenting skills following the Uncommon James founder’s December 2020 hangout with her ex-boyfriend Austen Kroll, she was also briefly linked to Cutler.

Jay Cutler’s Conflicting COVID-19 Views

In August 2021, Cutler alleged that Uber Eats dropped him from an ad opportunity because their “views aren’t aligned.” Days prior, Cutler expressed his interest in running for a position on the school board in Tennessee’s Williamson County after a temporary mask requirement was approved for the upcoming school year.

“Not this parent,” Cutler wrote via X at the time with an article about moms and dads calling for masks. “Really hope I’m not put in the corner by Twitter in my first 24 hrs.”

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Jay Cutler Arrested for DUI

The former NFL player was booked for a DUI at Nashville’s Williamson County Jail in October 2024, according to online records viewed by TMZ. The NFL star posted bond several hours later and was released. According to the outlet, Cutler was also charged with failure to exercise due care, violation of implied consent law and possession of a handgun while under the influence.

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