Kentucky Basketball sent Jon Gruden a box of gear for March

Did Jon Gruden just join the Big Blue Nation? Yes, that Jon Gruden, the former NFL coach who started his coaching career at Tennessee and whom the Volunteers lusted over for years.

Gruden now works for Barstool Sports and as part of his latest bit, has been unboxing gift packages from various football teams. The first college basketball team to send Gruden some gear? Your University of Kentucky Wildcats. This morning, Gruden uploaded a video of himself opening a box from Lexington. As he tries to cut through the packing tape with a drill, he talks about his memories of the Cats.

“Basketball? Coach Pope? I love Kentucky Basketball. They said they might send something. You know, when I was a kid, Kentucky Basketball, that was our archrival. Joe B. Hall was the head coach. Goose Givens. Rick Robey. Kyle Macy. But you learned to love them. They’ve got SGA, Karl-Anthony Towns. John Wall. What a tradition.”

While Gruden continues to struggle with the packing tape, he shares some advice for the Cats this March, using his “drills” catchphrase (and wearing a drill t-shirt).

“You know what the Wildcats need to do? Gotta start drilling some threes this time of year. Drill them, baby! Move that ball around. Dribble, drive, kick out, and launch some threes.”

“You ever heard of DeMarcus Cousins? They used to have a guy named Sky Walker. He had like a 58-inch vertical jump. How about Rick Pitino, man? Rick Pitino is the greatest coach of all time.”

“Thank you, Coach Pope. It’s our time of year. Playoff time. Wildcats! Drill some threes, man! Take it to the rack.”

After he finally gets the box open, he shows off some basketball moves with a football. Welcome to the bandwagon, Jon Gruden. We love that intensity.

Our first BASKETBALL box comes courtesy of Coach Pope and @KentuckyMBB! So much tradition and history, what an awesome gift to receive!

Just in time for the Tournament, too! pic.twitter.com/C88XPFsLBc

— Jon Gruden (@BarstoolGruden) March 13, 2025