It took just one day for Kentucky football to find its new coach.
But the work is just beginning in building the future of the program under Will Stein. Now, UK’s new coach must build a staff and roster in just a matter of weeks while also helping coach Oregon in the College Football Playoff.
Here is a rundown of important dates on the horizon for Stein and Kentucky.
Early signing period
The vast majority of high school prospects in the class of 2026 will sign with colleges Wednesday, so Stein has just one day to decide how many of the remaining 14 high school and junior college players who committed to play for Mark Stoops he plans to keep in the fold. It is possible he could land other uncommitted prospects before the December signing period, but it seems more likely any significant high school recruiting additions would come from the remaining unsigned players available in February. One piece of good news is Stein already has a relationship with four-star quarterback commit Matt Ponatoski, whom he recruited to Oregon before Ponatoski picked UK with the plan to play football and baseball in college.
New Kentucky football coach Will Stein reportedly plans to keep coaching at Oregon through the Ducks’ playoff run. Eric Evans Oregon Athletics
Kentucky transfer portal window
An NCAA rule change now allows players at schools that fire a coach to enter the transfer portal five days after the program hires a new coach. For Kentucky, that means current Wildcats can begin entering the portal this weekend, just less than a month before players at other programs can enter the portal on Jan. 2. Stein’s top priority this week has to be pitching the Wildcats with eligibility remaining whom he wants to retain. Those discussions will involve revenue sharing and NIL negotiations, so he must gain a quick handle on Kentucky’s roster budget.
Selection Sunday
ESPN reported Stein plans to remain with Oregon as the Ducks’ offensive playcaller through the team’s playoff run, which will be good publicity for Kentucky but adds additional scheduling headaches. The playoff field will be revealed Sunday, one day after the final conference championship games are played. Oregon is currently ranked sixth by the playoff committee, so it seems a lock to host a first-round game either Dec. 19 or 20. Quarterfinal games are scheduled for Dec. 31 and Jan. 1. The semifinals will be played on Jan. 8 and 9. The national championship game is set for Jan. 19.
Building a staff
Also on the agenda this week for Stein is deciding if he wishes to retain any coaches from the Stoops era to help establish some continuity in the program. Seven of Stoops’ assistants were coaching on expiring contracts this season, so do not expect more than one or two from that group to be kept. Stoops did not retain any assistants from Joker Phillips’ staff when he was hired at Kentucky, and Stein could elect for a completely fresh start as well.
Even if he does not keep any Stoops assistants, Stein will need to get at least a handful of staffers in place as soon as possible to help manage roster retention efforts while he splits time with his duties at Oregon. Since Stein will be one of the youngest head coaches in FBS football next season, expect him to add at least one veteran with head coaching experience to his staff. How he builds a support staff to focus on recruiting and roster management might be just as important. That could include making a general manager or chief of staff one of his first hires.
Mining the transfer portal
By hiring a coordinator, Kentucky is unlikely to see the same mass roster influx that some programs in the transfer-portal era have received by hiring sitting head coaches who bring many of their current players with them to a new job. Perhaps a handful of Oregon backups searching for larger roles will be interested in playing for Stein at Kentucky, but it is likely the bulk of Kentucky’s transfer portal work will focus on players from other programs. Even if all of Kentucky’s underclassmen return, starter-caliber transfers will be needed at a handful of positions. Work on finding possible additions will happen behind the scenes even before the portal officially opens in January. Once it opens, there will be a mad dash to sign transfers and get them on campus before UK’s spring semester starts Jan. 12. From there, Stein will need to begin preparing for his first spring practice and the installation of his vision for the program.
This story was originally published December 2, 2025 at 6:00 AM.
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Jon Hale
Lexington Herald-Leader
Jon Hale is the University of Kentucky football beat writer for the Lexington Herald-Leader. He joined the Herald-Leader in 2022 but has covered UK athletics for more than 10 years. Hale was named the 2021 Kentucky Sportswriter of the Year.
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