Kentucky Football's "Great Reset" Amidst Transfer Portal Surge

KSR · January 02, 2026 · Listen to Original Episode →

Original Title: 2026-1-2- KSR - Hour 1

TL;DR

New coach Will Stein's valuation of quarterback Cutter Boley was significantly lower than the Boley family's expectations, leading to Boley's departure and prompting Kentucky to actively seek a new starting quarterback.
The transfer portal's rapid opening and influx of player names highlight a shift towards faster decision-making, with over a thousand names appearing within hours of its launch.
Will Stein's proven track record developing quarterbacks like Bo Nix and Dylan Gabriel at Oregon suggests a strategic approach to finding and cultivating talent, contrasting with previous staff methods.
Kentucky Women's Basketball's upset victory over #5 LSU demonstrates the team's final four caliber and establishes them as legitimate contenders, controlling their own destiny in the SEC.
The departure of Cutter Boley signifies a "great reset" for the UK football program, with approximately 14 players already entering the transfer portal and more expected.
Kentucky Women's Basketball's success is attributed to a strategic emphasis on size and post presence, a departure from previous coaching philosophies and a key factor in their win.

Deep Dive

The core of this broadcast centers on the seismic shift in Kentucky's football program with the arrival of new coach Will Stein and the immediate fallout of the transfer portal opening, most notably the departure of quarterback Cutter Boley. This transition signals a fundamental re-evaluation of team strategy and player valuation, with the program now prioritizing a coach-driven assessment of talent and fit over established player loyalty or prior recruiting status.

The departure of Cutter Boley, a Kentucky native and the team's incumbent starter, highlights a critical divergence in how the previous and new coaching staffs valued players. While the previous staff was reportedly willing to significantly increase Boley's compensation to retain him, new coach Will Stein's valuation was considerably lower, suggesting a lack of alignment with Stein's system and personnel preferences. This decision underscores a new era of data-driven evaluation and budget management, where player value is assessed by the new regime, potentially leading to a more objective, albeit emotionally difficult, roster construction. The implications extend beyond just the quarterback position; this approach to valuation is likely to be applied across the entire team, leading to further roster turnover as players who don't fit Stein's vision or valuation are moved out.

Further compounding the narrative is the opening of the college football transfer portal, which has seen an unprecedented number of players enter immediately. Kentucky is actively pursuing high-caliber transfers, with multiple SEC offensive linemen reportedly visiting. This aggressive recruitment strategy, coupled with Stein's demonstrated success in developing transfer quarterbacks at Oregon--including Bo Nix, Dylann Gabriel, and Dante Moore--suggests a confidence in his ability to identify and integrate talent that fits his offensive system. The program is actively targeting top-tier quarterbacks, indicating an intent to upgrade the position rather than simply replace Boley with a similar player. This proactive approach to talent acquisition, leveraging Stein's established network and track record, positions Kentucky to potentially exceed fan expectations and rebuild a competitive roster rapidly.

In parallel, the Kentucky women's basketball team secured a significant victory against No. 5 LSU, demonstrating the program's readiness to compete at the highest level within the SEC. This win, clinched by a last-second three-pointer, signals that coach Kenny Brooks has built a team with the size and talent to challenge top-ranked opponents, a stark contrast to previous eras that lacked a consistent post presence. The team's dominance in rebounding and second-chance points against LSU underscores the strategic advantage gained from prioritizing size and physicality. This early conference success, especially on the road against a highly-touted LSU squad, establishes Kentucky as a legitimate contender and sets a high bar for future opponents in the increasingly competitive SEC.

The overarching implication is that both the football and women's basketball programs are entering periods of significant strategic realignment and elevated ambition. For football, the focus is on rebuilding through a coach-centric evaluation and recruitment process, emphasizing objective valuation and system fit. For women's basketball, the victory signifies a maturation into a top-tier program that can consistently compete for championships, leveraging size and strategic execution. Both narratives point towards a future where Kentucky athletics is aggressively pursuing success through calculated decisions and high-level performance.

Action Items

Audit quarterback evaluation process: Define 3-5 objective criteria for assessing transfer portal QB talent beyond past performance (ref: Will Stein's Oregon resume).
Create QB transfer target list: Identify 5-10 high-priority transfer portal quarterbacks with detailed profiles on their fit within Will Stein's offensive system.
Develop player retention strategy: Outline 3-5 key engagement tactics for retaining existing UK football players amidst transfer portal activity.
Measure impact of new coaching staff: Track 5-10 key performance indicators for offensive line development under new coaching staff within the first season.

Key Quotes

"The transfer portal opened 10 hours ago and i think there are more than a thousand names in it i don't know how it happened so quickly it's i'm i'm shocked how they they they make their decisions so fast yeah i mean you know obviously there were no conversations no no no it would be illegal so in the middle of the night so much has happened rausch and i were downstairs and joined a nice starbucks got our nice beautiful red cups here this was uh i bought today you know he made the trip from louisville you know nice 16 two cups of coffee here but no i bring that up we were down there just on our computers where we came up and it's just already the news is just one after another visitors departures uh it's gonna be busy keeping up with this for two hours while we're on ksr the rest of the day and it'll be fun because we we're not gonna stop the show for every single announcement of who's going in or what players visiting but i see shared five names at 12 01 last night and i think we've doubled that number of visitors since so uh the good i i think part of going into this that i was a little apprehensive about is that hey it's just it's a new coach so you don't know how they're gonna handle and then the new coach is also in the college football playoffs so like well how's he gonna do all that"

The speaker expresses surprise at the rapid pace of decisions and entries into the transfer portal, noting the sheer volume of names appearing shortly after its opening. This highlights the immediate and intense nature of player movement in college football under new coaching regimes. The speaker also touches on the challenge of keeping up with the constant stream of news during a live show.

"i would like to start by saying the best part of this story is that whether you white cutter boley and wanted him back or whether you hated cutter boley and are glad to see will stein pick his own guy quote unquote you had evidence to to back up your your argument right you had data points i mean if you just watched the last two louisville games you would say why would anybody want that guy to be their quarterback but then you watch some of the other games i mean you know he had the freshman record he broke the completion percentage record sec touchdowns record so there was there was some good to like there and there's also reasons why of course will stein and the new staff would say you know we're not sold on you and we're not gonna guarantee you anything and that was something will stein said on this show right couple weeks back um was that he's gonna be in here to compete and matt kind of pressed him a little bit um but he said no now you're going to be here to compete"

The speaker points out that there was ample evidence to support differing opinions on Cutter Boley's performance, citing both poor recent games and his past record-breaking statistics. This illustrates the subjective nature of player evaluation and the availability of data to justify various viewpoints. The speaker also recalls Coach Will Stein's previous statement about fostering competition rather than guaranteeing a starting position.

"i also thought it was you know it got there's a new agent that got in the mix in the last month so you know i felt bad for my man adam luckett because when he came in here with matt a couple weeks back when you guys were out you know i think he kind of got pressed into it and we were all we were operating under the assumption like hey it's a it makes sense for cutter boley to come back we think the money's good enough we think he's going to do it it's trending in that direction if you were making me handicap it you know plus or minus 250 that he's back at kentucky but you know what upsets happen yeah things they they things change in the transfer portal and um it's i like you said drew i think it is kind of it stinks because for so long we kentucky football fans have been reliant on transfer portal quarterbacks and you finally recruited one from high school that flashed and it's like okay well you bring in a quarterback coach who's been able to develop guys this all makes sense but in the transfer portal things don't always make sense right dollars and cents are what makes the most sense and so you know best of luck to boley he's going to uh get paid well"

The speaker reflects on how external factors, such as a new agent, can influence player decisions, and notes that assumptions about Cutter Boley's return were based on available information at the time. This highlights the unpredictable nature of the transfer portal and how quickly situations can change. The speaker also expresses disappointment that Kentucky football fans have historically relied on transfer quarterbacks and laments the potential loss of a high school recruit who showed promise.

"will stein his last he's had two 4 000 yard passers in his last three quarterbacks like it's just you're playing a different this is this is different so like of course we really propped up boley and you know what i like boley a lot i thought he had i liked what he had between the ears he was tough um you know he had some juice at his position that we hadn't had in a long time and his teammates really liked him like he had those good intangibles and and a lot of physical traits that you could build on and i i wanted to see like this would have been a real bet on himself situation right because he wanted to be at kentucky he i mean this is this is a team he grew up cheering for right but it would have been a bet on yourself so do you do the bet on yourself against a really tough schedule where there's some uncertainties about like how good are the guys going to be in front of me or around me or do you go to the big 12 where it's a league that's pretty easy to win outside of texas tech and byu the defenses aren't all that great like i'm gonna sling it around and go make some more money try some of the in the desert"

The speaker contrasts Will Stein's track record with high-yardage passing quarterbacks against the previous situation with Cutter Boley, suggesting a difference in offensive potential. This emphasizes the impact a coach's system and past success can have on player evaluation and team strategy. The speaker also acknowledges Boley's positive attributes and the difficult decision he faced regarding a "bet on yourself" scenario versus seeking financial gain in a potentially easier league.

"i do have a complaint why would you know i understand that kentucky lsu women's basketball isn't the rose bowl i know what you're gonna say but they probably could have found a channel for it somewhere right it was on sec plus you know just streaming only you know i i was able to go get it and find it and watch it over football but that that game too yep you know top 15 sec teams in the sec opener that should have been somewhere where more people could have seen it that's my one complaint i don't know what the sec

Resources

External Resources

Books

"Shot Ready" by Stephen Curry - Mentioned as a New York Times bestseller offering insights into his mindset and approach to success.

Articles & Papers

"Team Turmoil" - Mentioned in relation to a confirmed plane incident from over 20 years ago.

People

Cam Jordan - Host of the podcast "Off the Edge with Cam Jordan."
Anna Runkle - Creator, teacher, and guide known as "the crappy childhood fairy," featured on the podcast "A Really Good Cry."
Stephen Curry - NBA champion and author of "Shot Ready."
Lee Kemble - Lexington-based performer featured in New Year's Eve shows at Comedy Off Broadway.
Ray Lau - Comedian performing at Comedy Off Broadway in January.
Aaron The Lyle - AGT finalist performing at Comedy Off Broadway in January.
Will Stein - Offensive line coach and new head coach for the Kentucky football program, formerly an offensive coordinator at Oregon.
Cutter Boley - Former Kentucky high school quarterback who entered the transfer portal.
JP - Guest on the show who confirmed a plane incident from "Team Turmoil."
Kenny Dillingham - Head coach at Arizona State.
Sam Levitt - Arizona State's quarterback, considered a top transfer portal option.
Beau Nix - Former Oregon quarterback who became a Heisman Trophy finalist.
Dylan Gabriel - Former Oklahoma quarterback who played under Will Stein.
Jackson Arnold - Former Oklahoma quarterback.
Dante Moore - Former Oregon backup quarterback who was benched at UCLA.
Kenny Brooks - Head coach of the Kentucky women's basketball team.
Kim Mulkey - Head coach of the LSU women's basketball team.
Lane Kiffin - Head coach at Ole Miss, seen attending the Kentucky vs. LSU women's basketball game.
Tiani Key - Player for the Kentucky women's basketball team, noted for her stat line and offensive rebounds.
Clara Strack - Player for the Kentucky women's basketball team, noted for a game-tying shot and a foul.
Williams - LSU's best player, who made three free throws.
Asia Boone - Player for the Kentucky women's basketball team, noted for making five three-pointers.
Matthew Mitchell - Former head coach of the Kentucky women's basketball program.
Stephanie Okakuchu - 7-foot-tall player from Iowa State who signed to play with Texas Tech.
Phoenix Stevens - KSR contributor who predicted the Kentucky women's basketball upset win.
Andy - Caller to the show.
Matt Jones - Host of KSR.
Billy - Member of the KSR team.
Mario - Member of the KSR team.
Shannon the Dude - Member of the KSR team.
Rick - Member of the KSR team.
Drew Franklin - Host of KSR.
Ryan Lemond - Host of KSR.
Nick Roush - Guest on KSR.
TJ Smith - Personal injury attorney.
Gary - Mentioned in relation to Cornbread Hemp in Orlando.
Freddy - Former associate mentioned for his birthday and lunch.
Calzada - Mentioned in relation to a quarterback competition.
Adam Luckett - Mentioned in relation to Cutter Boley's situation.
Mitch Barnhart - Mentioned in relation to negotiations for Cutter Boley.
Ralph - Mentioned in relation to weight gain.
Brooke - Mentioned in relation to a New Year's Eve celebration.
Matt Doors - Mentioned in relation to KSR board posts.
Ryan - Mentioned in relation to Finny, a freshman defensive back from Oregon.
Diabate - Mentioned in a clip related to rebounding.
Georgia A'more - Mentioned in relation to the Kentucky women's basketball team's size.
Hasset - Player for the Kentucky women's basketball team.
Lynn Rollins - LSU legend and commentator for the Kentucky vs. LSU women's basketball game.

Organizations & Institutions

ivim - A medical weight loss program.
NFL (National Football League) - Professional American football league.
iheart radio app - Platform for listening to podcasts.
Apple Podcasts - Platform for listening to podcasts.
Liberty Mutual Insurance - Sponsor of the "Off the Edge with Cam Jordan" podcast.
Oregon - University mentioned in relation to Will Stein's coaching history.
Texas - University where C.J. Baxter played.
Arizona State - University reportedly interested in Cutter Boley and where Sam Levitt plays quarterback.
TCU - University mentioned in relation to Hoover.
Indiana - University mentioned as a potential lean for Hoover.
Denver Broncos - NFL team Beau Nix is reportedly heading to.
UCLA - University where Dante Moore was benched.
LSU - University and women's basketball team that lost to Kentucky.
SEC (Southeastern Conference) - Athletic conference mentioned in relation to football and women's basketball.
Texas Tech - University where Stephanie Okakuchu will play.
A&M - University where J.B. Bateman previously coached.
Florida - University where J.B. Bateman previously coached.
LCA - High school where Cutter Boley played.
The Black Effect Podcast Network - Network for the podcast "Reasonably Shady."
DraftKings Sportsbook - Official sports betting partner of the NFL.
Boot Hill Casino and Resort - Mentioned in relation to responsible gaming resources.
Adria Health Institute - Institution where Dr. Elizabeth Poyner is chair.
Kentucky - University and athletic program.
Ole Miss - University where Lane Kiffin is head coach.
Missouri - University and women's basketball team playing Kentucky.

Websites & Online Resources

ivimhealth.com - Website for the ivim medical weight loss program.
stephencurrybook.com - Website to order "Shot Ready."
comedyoffbroadway.com - Website for Comedy Off Broadway.
cornbreadhemp.com - Website for Cornbread Hemp products.
americanexpress.com/explore/bcp - Website for Blue Cash Preferred card information.

Podcasts & Audio

Off the Edge with Cam Jordan - Podcast hosted by Cam Jordan.
A Really Good Cry - Podcast hosted by Raddy Devlin K, featuring Anna Runkle.
KSR - Radio show/podcast.
Reasonably Shady - Podcast hosted by Giselle Bryan and Robin Dixon.
Decoding Women's Health - Podcast hosted by Dr. Elizabeth Poyner.

Other Resources

Transfer Portal - System for college athletes to transfer between programs.
Heisman Trophy - Award for college football's most outstanding player.
College Football Playoffs - Post-season tournament for college football.
Guardian Caps - Protective headgear.
NFL Blitz - Video game.
Peppermint Bark - A type of confection.
Pizza - A type of food.
Ribs - A type of food.
Cookies - A type of baked good.
Red Cups - A type of disposable cup, often associated with Starbucks.
Seltzers - Alcoholic beverages.
Sleep Gummies - Edible supplements for sleep.
Oils and Topicals - Products for relief.
Blue Cash Preferred - A credit card from American Express.
Cannabis and Cannabinoids - Substances discussed in relation to health benefits.
ADHD - Attention-deficit/hyperactivity disorder.
Dementia - A condition affecting memory and cognitive function.
Menopause - A natural biological process.
Player Props - Bets placed on individual player statistics in sports.
Baby Moons - Pre-baby vacations.
Steroids - Medications that can cause weight gain.
SEC Plus - Streaming service for SEC content.
SEC Network - Television channel for SEC content.
SEC Men's Basketball - Mentioned as being similar to the current SEC women's basketball landscape.
G5 Waters - Refers to Group of Five conferences in college football.
Heisman Trophy Finalist - A player nominated for the Heisman Trophy.
Offensive Line Coach - A coaching position in football.
Defensive Back - A position in American football.
Completion Percentage Record - A record for accuracy in passing.
SEC Touchdowns Record - A record for touchdowns scored in the SEC.
Freshman Record - A record set by a first-year player.
SEC Starting Left Tackles - Offensive linemen who start in the SEC.
3,000 Yard Passer - A quarterback who throws for at least 3,000 yards in a season.
4,000 Yard Passer - A quarterback who throws for at least 4,000 yards in a season.
Big 12 - A college athletic conference.
Texas Tech - University mentioned in relation to a 7-foot-tall player.
BYU - University mentioned in relation to the Big 12.
Texas - University mentioned in relation to the Big 12.
Texas Tech - University mentioned in relation to a 7-foot-tall player.
Big 12 - A college athletic conference.
SEC Opener - The first conference game of the season.
SEC Women's Basketball - Mentioned as being a strong conference this year.
Final Four - The semi-final stage of a tournament.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mentioned as being a strong conference this year.
SEC Women's Basketball - Mention