Jay Cutler Behind Bars? NFL Quarterback's DUI, Jail Time, and Net Worth Truths Exposed

Jay Cutler, the former Chicago Bears quarterback once worth millions, is heading to jail. The 41-year-old has been sentenced to four days behind bars after pleading guilty to a DUI charge in Tennessee.

He will begin serving his term on 29 September 2025 at Williamson County Jail. His plea deal also includes a £270 ($350) fine, one year of unsupervised probation, a mandatory DUI safety class, and the loss of his Tennessee driver's licence.

The conviction stems from an incident in October 2024 in Franklin, Tennessee, when Cutler rear-ended another vehicle, according to a report by ESPN.

Police said he showed slurred speech, bloodshot eyes, and other signs of intoxication. Officers also discovered two firearms in his truck, one of them loaded, although the weapons charge was later dropped as part of the plea agreement.

Authorities claimed Cutler tried to leave the scene and even offered the other driver £1,540 ($2,000) not to call police. The case marks one of the most serious legal setbacks faced by the ex-NFL star since his retirement.

NFL Millions at Risk

Cutler's career in the NFL spanned more than a decade with the Denver Broncos, Chicago Bears and Miami Dolphins. He signed lucrative contracts, including a seven-year, £93.7m ($126m) deal with the Bears, helping him earn more than £89m ($120m) over his career.

Today, his net worth is estimated at around £22.3m ($30m), according to Celebrity Net Worth. While this still places him among wealthy former athletes, his recent controversies have raised fresh questions over how stable his finances really are.

Endorsements and business ventures could suffer under the weight of his DUI conviction and negative headlines.

Divorce Row with Cavallari

Cutler's wealth has also been thrown into the spotlight by his divorce from TV personality Kristin Cavallari. The couple finalised their split in 2022, but Cavallari recently claimed she 'never got a penny' from the settlement.

Cutler hit back on his Take It Outside podcast, calling her remarks 'completely false' and 'borderline slander'.

According to People, a source close to Cavallari accused Cutler of twisting her words and labelled his response as 'gaslighting'.

Cavallari also stressed that her jewellery and lifestyle brand, Uncommon James, was entirely her own creation and not tied to their settlement.

The bitter exchange has fuelled debate about Cutler's true net worth, with fans questioning whether his finances are as secure as they appear on paper.

Backlash Over Hunting Photo

Adding to his troubles, Cutler sparked outrage after posting an image on Instagram of himself posing with a sable antelope he killed during a hunting trip in South Africa.

The photo drew fierce criticism online, with many branding it insensitive and unnecessary.

The hunting row, alongside his DUI conviction and divorce dispute, has kept Cutler in the headlines for all the wrong reasons.

Jay Cutler's Post-NFL Reputation

Once known as a talented but inconsistent quarterback, Cutler is now more associated with courtroom drama, financial rows and public backlash than his playing career.

His jail sentence for DUI, combined with scrutiny over his wealth and lifestyle choices, has left fans questioning how his legacy will be remembered beyond the NFL.