A key player for Kentucky football is expected to enter the transfer portal

Kentucky quarterback Cutter Boley is expected to be entering the transfer portal once it officially opens on Friday.
Nov 22, 2025; Nashville, Tennessee, USA;  Kentucky Wildcats quarterback Cutter Boley (8) scrambles against the Vanderbilt Commodores during the first half at FirstBank Stadium. Mandatory Credit: Steve Roberts-Imagn Images
Nov 22, 2025; Nashville, Tennessee, USA; Kentucky Wildcats quarterback Cutter Boley (8) scrambles against the Vanderbilt Commodores during the first half at FirstBank Stadium. Mandatory Credit: Steve Roberts-Imagn Images | Steve Roberts-Imagn Images

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As the clock strikes midnight on Thursday going into Friday, the NCAA transfer portal will officially be opened for college football. For Kentucky, one big piece for the 2026 season will be entering his name in. On Thursday, it was reported by On3's Pete Nakos and Steve Wiltfong that Kentucky starting quarterback Cutter Boley is expected to enter the transfer portal and exploring his options.

After redshirting his freshman season in Lexington, Boley was put into a starting role two games into the season as Zach Calzada suffered an injury, and the staff kept him as the starter from then on. It was clear Mark Stoops was building around Boley as his future quarterback, but once Stoops was let go, things changed. When Will Stein was hired as the new Kentucky head coach, he never firmly said if Boley would be his starting quarterback, Now, as the portal gets closer to opening, the Lexington native plans to look elsewhere.

In his first season as QB1, Boley turned himself into a quality quarterback in the conference, even earning All-SEC Freshman Team honors. He went on to total 2,160 yards, along with 15 touchdowns and 12 interceptions. Now that Boley is entering the portal, Stein will have to go searching for someone to takeover the role in Lexington. At his introductory press conference, Stein was asked what he looks for in a quarterback. First of all, Stein says he always plays to the strengths of the quarterback. What's he looking for in a quarterback's play-style and mindset? It starts with having a tough mentality.

"You start, kind of in your career, do they fit the measurables? But at quarterback, it's so much more than that. It's do they have the mental makeup to be the top, toughest M'Fer on the field? Because that's what they got to be. They got to be mentally and physically tough. That's really where it starts with me, and then processing ability, being extremely accurate thinking. If you look at the guys that I've coached recently, all over 70% passers, if you're not over 70% High School, it makes you think you're going to be 70% college. So we look at that, arm talent only takes you so far. You rarely ever throw it 70 yards, unless it's a Hail Mary situation. So can you be accurate? Can you throw on time? Can you withstand the confines of a pocket? And then in today's modern football, you got to be mobile."

According to KSR's Matt Jones, Arizona State is a team to watch as a landing spot for Boley. As far as targets to replace him, Stein will have plenty of options to choose from. The new Kentucky coach has such an exciting offensive system, so it will be really intriguing to see who he has in mind.


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Wyatt Huff
WYATT HUFF

University of Kentucky Basketball and Football beat writer.

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