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Former football star Jay Cutler is in jail.

Though Kristin Cavallari’s ex-husband is no stranger to scandal, his arrest and the long list of charges took many by surprise.

Now, he is behind bars, serving out his sentence.

What a mess!

Jay Cutler mugshot in October 2024.
In this handout provided by the Franklin Police Department, former NFL quarterback Jay Cutler poses for a booking photo after being arrested on charges of a DUI and possession of multiple weapons while intoxicated on October 17, 2024. (Photo Credit: Franklin Police Department via Getty Images)

Jay Cutler is in jail, but not for long

On Monday, September 29, former football player Jay Cutler began serving his sentence in Williamson County Jail in Franklin Tennessee, TMZ reports.

This four-day jail sentence is the result of a deal that he struck with prosecutors.

As part of the deal, Cutler pleaded guilty to one count of misdemeanor DUI.

In turn, prosecutors dismissed the weapons charge that he had been facing.

Jay Cutler in December 2022.
Former quarterback of the Chicago Bears, Jay Cutler, looks on before the game against the Green Bay Packers at Soldier Field on December 04, 2022. (Photo Credit: Quinn Harris/Getty Images)

In October 2024, Cutler rear-ended another vehicle during a traffic accident.

Police observed signs of intoxication, including slurred speech.

Cutler refused to take a field sobriety test.

However, a blood-alcohol test ensued. Authorities also found two firearms, one of which was loaded, in the vehicle.

Jay Cutler racked up a list of criminal charges

As a result, Jay Cutler faced a litany of charges.

These included charges of driving under the influence, reckless driving leading to a collision, violating implied consent regulations, and unlawfully possessing a firearm while intoxicated.

Considering all of that, pleading guilty to just one charge and getting four days behind bars doesn’t sound too bad.

Jay Cutler in October 2017.
Jay Cutler #6 of the Miami Dolphins heads off the field after the game against the Atlanta Falcons at Mercedes-Benz Stadium on October 15, 2017. (Photo Credit: Scott Cunningham/Getty Images)

In addition to spending part of this week in jail, Cutler must pay a $350 fine.

(Considering his estimated net worth of about $30 million, imagine if someone with a net worth of $85,000 had to pay $1)

He will have to serve one year of unsupervised probation.

His driver’s license suspension will last for the same duration. And he must attend a DUI safety course.

Jay Cutler in September 2017.
Jay Cutler #6 of the Miami Dolphins loooks on after their 20-6 loss against the New York Jets at MetLife Stadium on September 24, 2017. (Photo Credit: Al Bello/Getty Images)

How did this happen?

Again, since Jay Cutler agreeing to this deal meant that almost all of the charges vanished into thin air, this is a very favorable deal. For Cutler — not necessarily for his fellow citizens.

Driving under the influence has never been okay. DUIs are even harder to understand now, when most people in most places could obtain a ride with the push of a few buttons on their phone.

Sometimes, a DUI happens once due to a simple misjudgment.

The unlicensed firearm seems more serious and more difficult to explain, however.

Plenty of yikes all around.