RETENTION: Kentucky Football Players Will Stein Needs to Prioritize Ahead of Transfer Portal

It’s a new era for Kentucky football. The early days of Will Stein‘s tenure are focused on assembling a coaching staff, while juggling CFP prep at Oregon, before building the 2026 roster.

In Mark Stoops’ final weeks as the Kentucky head football coach, his primary focus was retention. The Cats had a young corps worth building around, and Cutter Boley was the centerpiece. After the blowout loss to Louisville, Stoops said that a nucleus of players had already signed contracts to return for the 2026 season.

I’m not a lawyer, and I haven’t seen the contracts. But everything that I’ve gathered over the last two weeks is that those players are not contractually locked in for next season. The Stein administration will have new proposals to share with players before the transfer portal opens on Jan. 2. Who should be the top priorities? That’s the question we’re answering today.

Cutter Boley

“A bird in the hand is worth two in the bush.”

Stein has every right to pick the quarterback he wants for this offense. If he doesn’t think it should be Cutter Boley, that’s his right as the head coach. Some will point to Boley’s numbers on the road (57.9%, 5 TDs, 9 INTs) as a reason to move on, while conveniently ignoring that his stats at home (74.6%, 10 TDs, 3 INTs) helped him break the UK freshman record for completion percentage and TDs vs. SEC competition. It costs more to bring in a player from the open market than to retain one. Keeping Boley makes the roster build much more palatable, especially when they’ll be in the market for expensive offensive linemen.

Kentucky Pass-Catchers

You don’t have to be an insider to know that Vince Marrow will want to bring Willie Rodriguez to Louisville. One of Boley’s favorite targets, the tight end had 24 receptions for 310 yards and a touchdown. He improved from year one to year two, and there’s a ton of potential for growth in Stein’s scheme.

Three other young wide receivers flashed this fall with Boley: DJ Miller, Cam Miller, and Hardley Gilmore IV. They contributed in clutch moments for the Cats. If they can get all three in the fold, there’s room to go all-in and make a splash with a veteran in the transfer portal.

DJ Miller Stock 📈🔥 pic.twitter.com/wjcS6uNCTO

— Blue Chips Media (@BlueChipsBBN) October 26, 2025

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Mi’Quise Humphrey-Grace and the Defensive Line

Mi’Quise Humphrey-Grace didn’t have the most jaw-dropping numbers, but he was the most impactful player in a couple of games. While Diego Pavia slipped away from most in the SEC, No. 90 sacked him twice. After LaNorris Sellers got away once, Humphrey-Grace got home on a third down that knocked South Carolina out of field goal range. He would command top dollar on the transfer portal market, which is why Kentucky needs to lock him down.

Tavion Gadson had the second-highest pass rush grade in the SEC among defensive tackles, according to PFF. Locking in Gadson also locks in his brother, redshirt freshman Lorenzo Cowan, who flashed on the EDGE at the end of the season, forcing two fumbles. Speaking of EDGE players, Steven Soles had the fourth-highest pass rush grade among players at his position in the SEC. He had a win rate of 16.2%, the seventh-highest among players with at least 100 attempts.

Grant Godfrey

As Adam Luckett wrote earlier today, linebacker is a major need for Kentucky in the transfer portal. Grant Godfrey is the only projected returner, and they need to make sure he returns. Godfrey earned multiple starts down the stretch and showed exceptional closing ability, and made tough tackles in open space. “Not to look too far into next season, but I think he’s on the right track to be one of the guys in the SEC,” Daveren Rayner said during the final week of the regular season.

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Kentucky Secondary

The Cats are kind of a mess at cornerback. They have 10 players in that room. Grant Grayton was forced to play a lot as a true freshman and got picked on at times. Terhyon Nichols and DJ Waller look like SEC cornerbacks, but have missed a significant amount of time with injuries. There needs to be some attrition and it’s anybody’s guess what will happen when the portal opens.

There is a clearer picture in the back half of the secondary. Ty Bryant led the SEC in interceptions. Second-year players Cam Dooley and Quay’sheed Scott had a few mistakes you’d expect from young players, but they look like guys you can build around.

Prepare for Player Movement when the Portal Opens

In conclusion, this is a new coaching staff. You should expect major roster turnover. The key for Stein is ensuring that the best of the best doesn’t get left behind.

“If you turn on the tape, there’s some elite characteristics from a lot of guys on the squad,” Stein said on KSR last week. “I think we just got to continue to push them and continue to create accountability within the team, and toughness, and be great in all three phases.”