Until Oregon was eliminated from the national title race after its loss to Indiana in the Peach Bowl, former Ducks offensive coordinator and QBs coach Will Stein was juggling a rare and gruelling double duty. As he called plays and guided Oregon through the College Football Playoff, Stein simultaneously faced the pressures of his new Kentucky head coach role. It was a demanding overlap that would soon take a personal toll on his family.

Will Stein had to sacrifice precious moments with his family to avoid any distractions from his coaching role. Things got even more complicated for Stein after taking full control of Kentucky’s head coaching job. But the positive thing about the end of Stein’s double-duty grind is that he’s able to carve out some time for his family. A recent family moment was captured by his wife, Darby, who shared it on social media, showing Stein making up for lost time.

“Reunited after 21 days apart,” Darby wrote on her Instagram stories, sharing a picture of Will Stein’s son, Joey, leaning on his father’s right shoulder and the Kentucky HC’s daughter, Demi, sitting on his lap, full of affection and love.

On Saturday, Cats Coverage reposted the image with a perfectly timed caption, “The reality of being a Division I head football coach.”

Coaching is by no means a walk in the park. Every decision, from players to program development, is under scrutiny. However, managing OC duties alongside is believed to be an even harder endeavor. When, on December 1, 2025, Stein officially took the Kentucky head coaching job, it came at a crucial time for the Ducks, who were deep in the playoff hunt. And while many would have struggled to juggle multiple roles, Stein maintained both at his best.

Under Will Stein’s guidance, Oregon defeated JMU and Texas Tech in the first two rounds of the CFP but fell 56-22 in the semifinal. Still, the run clearly indicates the level of Stein’s dedication to his responsibilities. On the flip side, he honored all 11 high school commitments made by the previous staff under Mark Stoops for the 2026 class, as the new UK coach wanted those players to meet him, know him, and earn their spot.

The transfer portal opened on January 2, right as Oregon was gearing up for the CFP semifinal. Stein didn’t miss a beat in rebuilding the UK’s future, inviting some high-profile targets and holding meetings with them. The momentum was starting to build.

Will Stein’s dedication wasn’t just confined to the gridiron; his commitment to family, even amidst the chaos, painted the full picture of the man Kentucky hired. And while the reunion photo captured the family’s side of the story, Stein himself later offered a painful confession about the personal cost of his ambition.

“I was told I looked refreshed today. I have not felt that way, that’s for sure. It’s not easy for anybody. Is it difficult? Sure. It’s difficult across the country, though. Everybody’s dealing with it. Oregon is, IU is, it’s going on everywhere. So there are distractions out there that you just handle,” Stein said during the Ducks’ post-season push.

Well, things are looking good for Will Stein. That’s only because he has more time to spend with his family, but also because his family has benefited from his appointment as the Wildcats’ head coach. And at the forefront of that benefit is Stein’s mother.

Will Stein’s HC appointment boosts his mother’s bakery in Louisville

Will Stein’s mother, Debbie, and her sister, Blakey Martin, used to be revered by a smaller fan base for their family-famous orange cake in a bakery in Louisville named Sissy Cake. This small fan base usually included family, friends, and the extended clan. However, their stock skyrocketed in Louisville, making its way into school lunches and becoming a preferred snack during football practice sessions.

This surge in their sales comes right after Will Stein became the head coach of Kentucky. Although there is no definitive report that the appointment was the reason behind his mother and sister’s growing business, the sisters appear convinced that the good things were happening because of William, which is the name they call him by.

“We thought, well, that’s adorable,” Blakey Martin stated during an interview with the Courier Journal.

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Besides giving his family some much-needed time, Stein also gave his all to a program that had meant a lot to him before fully stepping into the next chapter. It remains to be seen how the Kentucky journey pans out for him in the coming season. Let us know your thoughts in the comments below.