The last 48 hours have been a whirlwind for the Boley family - and that’s saying something for a household that’s already been through the high-stakes world of high school recruiting once before.
Back in 2016, Scott Boley watched his daughter, Erin, navigate the national spotlight as the Gatorade High School Basketball Player of the Year before committing to Notre Dame, and later transferring to Oregon. But even that didn’t quite prepare him for what’s unfolded this week surrounding his son, Cutter Boley - Kentucky’s redshirt freshman quarterback - in the wake of a major coaching shakeup in Lexington.
“This has surpassed anything we went through with Erin,” Scott Boley said.
Kentucky’s decision to part ways with longtime head coach Mark Stoops on Sunday sent shockwaves through the program. But by late Monday night, the program had its new leader: Will Stein, the former Oregon offensive coordinator.
And for the Boleys, that name rang a familiar bell.
“I think it’s a great hire,” Scott said. “He came to Lexington a few times and watched Cutter’s workouts at LCA.”
At the time, Stein was working as Oregon’s quarterbacks coach, and he’d already shown interest in Cutter during the recruiting process. In fact, Cutter received a scholarship offer from Oregon during his junior year - an offer extended by then-offensive coordinator Kenny Dillingham, before Dillingham left to take the head coaching job at Arizona State.
So when Stoops’ future at Kentucky started to look uncertain, Stein was already top of mind for the Boley family.
“I’d be lying if I didn’t admit that for selfish reasons, I like the hire,” Scott said. “He really liked Cutter during recruiting. When things started going down with Stoops, Will was probably my first thought.”
Still, the coaching change caught the family off guard. Scott said he believed Stoops was coming back for another season, and Cutter did too. But after back-to-back losses to Vanderbilt and Louisville to close the regular season, momentum shifted quickly.
“In my opinion, those losses pushed it over the edge,” Scott said. “Even Saturday night after the Louisville game, I didn’t know anything was going to happen.”
Now, with the coaching transition official, the attention turns to what comes next - not just for Kentucky, but for Cutter Boley and the rest of the roster.
Under NCAA rules, players are allowed to enter the transfer portal within a 15-day window beginning five days after a new head coach is hired. For Kentucky players, that means the portal could open as early as Saturday.
While no formal contact from other programs is allowed just yet, the backchannel conversations have already started - as they often do in today’s college football landscape.
“Nobody can contact players directly yet, but there are a lot of go-between conversations to let you know people are interested,” Scott said. “We know a lot of quarterbacks across the country.
Cutter went to a lot of camps. The truth is, quarterbacks usually know where they’re going before the portal even opens.
They don’t just jump in and wait to see what happens.”
That’s the reality of the modern game. But for Cutter, this is still very much his decision - just like it was when he committed to Kentucky over a host of powerhouse programs, including Florida State, Michigan, and Penn State.
“We could’ve tried to talk him into something else, but it would’ve been impossible,” Scott said. “He would have refused to listen. We can advise him now, tell him what we think, but it’s still all his decision.”
And make no mistake - Cutter still has deep ties to the program and the community.
“Nothing has changed about how much he loves this fanbase, the school, the whole place,” Scott said. “He really does love it.”
Of course, the long-term goal remains the same: the NFL. And that means Cutter has to be in the right situation - one that protects him physically, develops him mentally, and showcases his skill set.
“The most important thing is putting himself in the right situation, and I certainly hope that’s here,” Scott said. “He can’t be medically retired before he gets out of college.
That can come down to the offensive scheme. It’s more than just the offensive line.
I thought the majority of the year, our line played pretty well.”
But the hits Cutter took this season weren’t lost on his family.
“He took a beating many times this year,” Scott said. “We don’t want him crippled when he’s 25.
I know football players get beat up, but a quarterback shouldn’t look like Cutter did 24 hours after some games. We just want him to be in the best situation possible.”
Stein met with the team on Tuesday and is set to hold a press conference this afternoon. It’s expected that he’s already had a chance to sit down with Cutter - not just to talk about the future of the quarterback position, but to get a feel for the locker room. A player like Boley, with credibility and leadership potential, could help stabilize the roster and even offer insights into personnel decisions as Stein builds his staff and system.
Speaking of Stein’s staff, multiple reports indicate that former Lexington Catholic and Louisville quarterback Justin Burke is expected to join the team. Burke, who’s been the offensive coordinator at UT San Antonio, has a history with Stein - the two were on staff together at UTSA before Stein made the move to Oregon.
So, while the last 48 hours have been a storm of change, there’s a sense of cautious optimism in the Boley household. Cutter’s next step isn’t set in stone, but the pieces are starting to fall into place. And if Stein can build the right system - one that protects his quarterback and plays to his strengths - there’s a real chance that Cutter Boley’s future still runs through Lexington.