Nothing quite prepared him for navigating the recruiting circus as a parent. The ESPN analyst recently opened up about his youngest son, Chase, and his recruitment journey through the Class of 2025. What stood out most from his comments was a revelation about one program his son was interested in that never reciprocated. It was North Carolina under Bill Belichick.​

“I talked with a lot of college coaches, and their recommendation was to send my son to schools he was interested in,” Kirk revealed during his conversation with Greg Olsen for Youth Inc. “So he was interested in North Carolina, he was interested in North Carolina State, he was interested in Notre Dame with Marcus Freeman, and he was interested in Michigan.

“And so we went to the actual camps, where their coaches would actually be out with the running backs, with the tight ends, the tight end coaches, with the tight ends, the North Carolina tight end coaches with the tight ends and doing drills with them. The quarterback coach, the real North Carolina quarterback coach, was with the quarterbacks, and he’s watching my son and maybe seven or eight others work out,” Kirk explained. “You’re planting some seeds just by going to these individual camps.”

The interesting thing is Chase clearly had an interest in North Carolina, attending their camp and working out in front of their coaching staff. But then UNC made the shocking move to hire Bill Belichick in December 2024. When Belichick took over, he brought his own vision for the quarterback room. And apparently that vision didn’t include Chase Herbstreit.

Despite Chase attending North Carolina’s camp and showing interest in the Tar Heels, Belichick never extended an offer. The six-time Super Bowl champion was busy building his own roster with his own guys.

So Chase ended up at Michigan, joining Sherrone Moore’s 2025 class as a walk-on quarterback. The 6-foot-2, 185-pound signal-caller wrapped up his senior season at Cincinnati’s St. Xavier High School with 18 passing touchdowns and eight rushing scores, leading his team to a regional final.

He enrolled at Michigan alongside Bryce Underwood, the No. 1 overall prospect in the 2025 class, creating one of the more intriguing quarterback rooms in the Big Ten. For Kirk, watching his son commit to Michigan, where he’ll wear the maize and blue his father spent years competing against, had to sting a little. But at least Chase found a home, even if Bill Belichick and North Carolina never saw what was right in front of them at that camp.​

The transfer portal’s hidden cost

Now that Chase is settled at Michigan, Kirk’s getting an up-close look at another ugly side of the transfer portal that nobody talks about. It’s the financial chaos it creates for the players left behind. During a recent podcast with Joey Galloway, the ESPN analyst revealed that one of Chase’s roommates at Ann Arbor has already entered the portal and disappeared. It has left Kirk scratching his head about who’s covering the bills.

“One of Chase’s roommates is gone up at Ann Arbor,” Kirk Herbstreit said, “So, I was like, I asked Chase, I was like, if he leaves do we cover his rent? I don’t know what’s going on here.” Galloway jumped in, “What happens when you jump in the portal, and you’re waiting around, but that rent payment is still coming due? I don’t know how that works.”

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For Chase, dealing with roommate drama is just another layer of complexity in an already intense situation. He’s grinding to prove himself in a quarterback room where he’s clearly not QB1. And now he’s potentially stuck covering rent for someone who bailed for greener pastures elsewhere.