Jon Gruden hasn’t coached in the NFL since October 2021 after old emails surfaced showing racist and homophobic language. Four years later, he’s still finding ways to grab attention.
Jon Gruden and Jake Malasek's Chicago Cab Driver Gives Them the Ride of Their Lives
Jon Gruden and Jake Malasek’s Chicago Cab Driver Gives Them the Ride of Their Lives (Screenshot Via X/@BarstoolGruden)
This time, it’s not play calls or press conferences doing the talking. Gruden just posted a random taxi video that has fans across the internet laughing nonstop.
Jon Gruden and Jake Malasek’s Chicago Cab Driver Gives Them the Ride of Their Lives
Gruden joined Barstool Sports last November after spending 2023 as a consultant with the Saints. The 61-year-old has built a massive social media following with his loud, unfiltered personality. On Friday, he delivered peak Chuckie content.
The former Super Bowl championposted video footage of himself and Barstool colleague Jake Malasek cruising through downtown Chicago. Their cab driver wasn’t messing around. The guy drove straight through the shoulder lane while Gruden provided ESPN-style commentary from the backseat.
The taxi @jakemalasek and I took from O’Hare into Chicago the other night was one of the crazier rides of our lives…
He may have driven in the shoulder the entire ride, but he got us downtown in record time! It was crazy! pic.twitter.com/pIWSMhWrdK
— Jon Gruden (@BarstoolGruden) October 17, 2025
You can hear Gruden’s mix of fear and excitement as the driver moves quickly through traffic. The clip captures everything from loud horns to tight turns and Gruden’s raspy voice reacting to every close call.
It shows exactly why fans loved him on Monday Night Football, where his energy and big reactions made every game feel special.
The coach has been vocal about wanting to return to the sidelines. He’s even said he’d coach junior high if that’s what it takes.
But his second stint with the Raiders didn’t exactly scream “hot commodity.” Three seasons of 4-12, 7-9, and 8-8 records before the scandal hit.
His career numbers tell a mixed story. Gruden went 117-112 across 15 seasons with Oakland and Tampa Bay. Sure, he won Super Bowl 37 with the Bucs in 2003.
But that championship team? Built by Tony Dungy, the coach Gruden replaced.
NFL Fans Can’t Stop Laughing at Gruden’s Chicago Adventure
Social media lit up when the video dropped. The reactions ranged from pure comedy to classic Chicago pride.
One fanwrote, “Getting the Coach where he needs to be. He ain’t playing.”
A secondadded, “Jon you’re the man but we can’t condone these types of assholes on the road!”
A thirdnoted, “Bro is definitely not from here.”
Not everyone found it funny. A fourthpointed out, “We call this ‘Dry Snitchin’…” Others saw it as peak Chicago behavior.
A fifthobserved, “This is the most Chicago thing I’ve seen this week.”
The video shows Gruden still has the charisma that made him a TV star. Whether he ever coaches again remains anyone’s guess. For now, he’s living his best life making viral content in the back of Chicago cabs.