'I felt like the President': Will Stein's wild first 24 hours as Kentucky's coach

It’s been a whirlwind week for Will Stein. On Saturday, Stein was on the sideline coaching in Oregon’s final season game at Washington. On Tuesday afternoon, he touched down in Lexington in a private jet as Kentucky’s new head coach. That’s the moment it all became real for the 36-year-old Louisville native, who grew up going to Commonwealth Stadium, where his father played in the 1980s.

“I was, like, floored yesterday when we landed,” Stein said during his introductory press conference. “We got off the cool private jet that they flew us on — it’s pretty great, Mitch, thank you for that — I’m not kidding. There were 15 cop cars in front of our car and 15 cop cars behind our car. I felt like the President of the United States. I was like, What in the heck is going on?”

Stein took a photo with his phone to preserve the memory.

“I have never seen anything like that, so it kind of woke me up. I was like, This is a big-time gig. This is big-time. That was probably the most surprising to date.”

After meeting with the team, things only got more surreal for Stein. He arrived at Rupp Arena two hours before Kentucky Basketball’s game vs. North Carolina, making the rounds and greeting fans. Rupp is another building he’s familiar with, as his family had season tickets to men’s basketball and football growing up, but on Tuesday, he was the biggest VIP, even eclipsing former Kentucky Basketball greats Rajon Rondo and Tayshaun Prince. Prince was already scheduled to be the honorary Y, but when Stein was hired, UK decided to make him one too, the first time Kentucky has had two Ys in one game.

“I’m like, you’re choosing me over Tayshaun?” Stein said. “What the hell is going on here? It was really a special, special moment.”

A special moment he doesn’t entirely remember, he admits.

“I actually blacked out, to be honest. I didn’t really know what was going on. I know I did a lot of fist pumping and yelling. The cheerleaders that escorted me out, I think I wrestled away from them to get going as quickly as I could.”

Thankfully, plenty of phones were out to record this one for posterity.

Doing The "Y" – Bringing the energy!@CoachWillStein x @KentuckyMBB x @Rupp_Arena pic.twitter.com/nRhPtado5U

— Kentucky Football (@UKFootball) December 3, 2025

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Will Stein on Sissy Cake’s boom

By now, you’ve surely heard of Sissy Cakes, the bakery that Stein’s mother Debbie and aunt Blakey own and operate in Louisville. On Tuesday, KSR special correspondent Jay In Lyndon went to Sissy Cakes to get Debbie on the phone to talk about her son, an interview that got a shoutout from Stein during his press conference on Wednesday.

“I think we need to get like an SID for my mom or something,” Stein joked. “I see a video, she’s talking to KSR. Holy crap, right? This is going on. Might need some detail on that.”

Business has been booming at Sissy Cakes to the point that they had to turn off online ordering due to high demand. Stein said his mother and the family bakery becoming famous is another awesome part of it all.

“I mean, it’s wild,” Stein said on his interview on KSR this morning. “It’s really kind of funny to me, to be honest.”

“The cakes are phenomenal. There’s no doubt about that. They are the best cakes you’ll ever have in your life. Sissy cakes. I’ll give a shout-out to them. Blakey and my mom, they’ve been doing it now for years. During COVID, they started to make it like a business and said, you know what? Why don’t we do this? So I’m really proud of them and their success. They’re just kind of a small bakery now, so they need as many orders as they can, but they’re going to be grinding. I don’t think she’s ever going to see me play a game; she’s going to be baking cakes all the time.”

Time for Sissy Cakes to open another location in Lexington.