Scandals That Have Soured Former NFL Player Jay Cutler's Reputation

Jay Cutler — former NFL player and ex-husband to reality TV personality Kristin Cavallari — has rarely caught a break during his years in the spotlight. From his time as one of the most hated pro football players to his later role as a crabby reality television spouse (and, later, divorcé), Cutler has been front and center of scandal after scandal over the years. One of the earliest and the biggest arrived during the third season of the E! series “Very Cavallari,” when rumors surfaced that Cutler was involved in an affair with his wife’s best friend Kelly Henderson.

On the show, Cavallari denied believing the rumors but was upset with how Henderson handled the situation. Nevertheless, the speculation gained traction as social media buzzed with talk of the affair after Henderson posted a photo of a man wearing a bracelet similar to one Cutler owns. Though Cavallari stood by her marriage, putting the blame for the rumors on Henderson rather than Cutler, there’s no doubt his part in the scandal did some damage to his rep.

As such, few were truly shocked when Kristin Cavallari officially filed for divorce in April 2020 … mere weeks after the cheating scandal aired on the third (and final) season of “Very Cavallari.” Cavallari accused husband Jay Cutler of inappropriate marital conduct and cited irreconcilable differences as the reason for their split. According to court documents, Cavallari claimed that continuing to live together would be “unsafe and improper” due to Cutler’s behavior. “She denies that Husband has always been the available at home parent and primary caretaker of the parties’ minor children,” her legal filings further read (via TMZ), saying that she was the true primary caretaker of their children.

These accusations painted Cutler in an increasingly negative light, especially considering how soon after the whole Kelly Henderson thing the divorce came through. Cavallari’s allegations of inappropriate conduct suggested deeper issues in their marriage, and fans of the couple began to question how much of their seemingly picture-perfect life had been an illusion. Unfortunately for Cutler, it wouldn’t be the last scandal, either.

Apparently, behind closed doors, Jay Cutler’s temper had become a point of contention — both in his marriage and while filming “Very Cavallari.” In divorce docs, Kristin Cavallari claimed that he was prone to making inappropriate remarks and provoking arguments in front of their children. His behavior often embarrassed his then-wife, a source told Us Weekly, particularly during public outbursts or on-set confrontations (where he was said to be known for being unpleasant to the crew). If Cutler’s reputation hadn’t been muddied by now, it certainly wasn’t the same after this development.

“We definitely kept a lot of stuff private,” Cavallari told People of their marital issues. “Producers saw stuff, but they didn’t put it in the show — which is good, because I don’t want my kids to ever [see that].” Once the divorce went public, it was revealed she’d tried to create a healthier environment for their children by moving out of the family home completely. It’s not hard to believe, considering what Cutler’s former teammate Devin Hester said about him on “Club Shay Shay.” Explaining why he had called Cutler a terrible leader, Hester stated, “He was standoffish … he just kept himself away from everybody and wasn’t friendly about it.”

During their divorce proceedings, Kristin Cavallari accused Jay Cutler of withholding money from her — a move she believed was motivated by her refusal to agree to his divorce settlement demands. An insider told Us Weekly, “Kristin always knew that Jay was trying to keep some of his money from her,” adding, “She suspected this for a while and found some type of proof.”

This allegation was brought to light when Cutler initially refused to release money for her to purchase a new home, forcing Cavallari to fight for financial independence for herself. Cavallari stuck to her truth, while Cutler’s decision to keep money from his estranged wife only further painted him as vindictive and petty during the divorce process. To the public, Cutler’s reputation would never be the same after using money as leverage like this.

In May 2021, Jay Cutler added another layer to his already tarnished reputation by attempting to claim half of Kristin Cavallari’s business Uncommon James: the jewelry and lifestyle brand that she says she founded all by herself. Although Cavallari said she started the business on her own, Cutler sought a share of it simply by association of marriage. This added a ton of fuel to their legal fire … and only made things look worse for Cutler.

Still, insiders told TMZ that Cavallari was pushing back hard on Cutler’s claim, arguing that he had no entitlement to the company since he didn’t contribute financially. Cutler’s pursuit of half of Uncommon James further sullied his reputation with the public, revealing him to be someone looking to capitalize on his ex-wife’s hard work. The battle over the business painted a picture of a desperate man trying to claim more than what was his in the marriage — not a good look, to be sure.

Most recently, Jay Cutler’s reputation took an even bigger nosedive. In October 2024, Cutler was arrested in Franklin, Tennessee, on charges of driving under the influence and illegal possession of a firearm. The Franklin Police Department revealed that Cutler had rear-ended another vehicle in the affluent Nashville suburb’s downtown area. While speaking with Cutler, officers noticed a strong odor of alcohol on his breath along with slurred speech and bloodshot eyes.

Cutler refused a sobriety test, leading to his immediate arrest, at which point officers found two firearms in his car. From his hard time in the NFL to his rough go of it on reality TV to his messy divorce unfolding in the public eye, this arrest was yet another blow to the already crumbling reputation of Jay Cutler. His is a lot more than a fall from grace: It’s practically a leap.