College athletics is rapidly evolving into a more professional model, and with NIL, the transfer portal, and roster management becoming more complex than ever, schools are starting to hire general managers to assist head coaches. Kentucky is in a prime position to lead the charge, with its deep resources, strong basketball tradition, and fanbase that expects national title contention every year.
If Kentucky does make the move to hire a GM, there are plenty of fascinating options. Some bring legendary status, others NBA front-office experience, and some have deep ties to Mark Pope and the Kentucky program. Here are six of the best candidates for the job:
1. Rick Pitino – The Fan Favorite with Unmatched Connections
If Kentucky wants a splashy hire that energizes the fanbase, look no further than Rick Pitino. The Hall of Fame coach led Kentucky to a national championship in 1996 and still has strong ties to the program and Big Blue Nation. Pitino has built programs at every stop, and his connections in college basketball, the NBA, and even overseas would be invaluable in roster building.
He is nearing retirement from coaching, but he will surely want to stick around. If anyone could step into a GM role and immediately elevate Kentucky’s recruiting and NIL strategies, it’s Pitino.
2. Larry Bird – The Basketball Genius with Front Office Success
One of the greatest players ever, Larry Bird also has legitimate executive credentials. He won NBA Executive of the Year with the Indiana Pacers and currently advises their scouting department. Bird’s basketball IQ is second to none, and his ability to evaluate talent—especially at the pro level—would be a game-changer for Kentucky.
The biggest question? Would Bird be interested in the college game. If he is, Kentucky would be getting a legend with a sharp mind for the modern game.
3. Ettore Messina – The International Guru with Spurs Influence
A name that may not be as familiar to Kentucky fans, but Ettore Messina is one of the best basketball minds in the world. He’s been a top assistant with the San Antonio Spurs, coached internationally at the highest level, and is widely regarded as a master strategist.
Mark Pope has deep respect for the way the Spurs play, making Messina an intriguing fit. His connections in European basketball could open new doors in recruiting, especially with more international prospects making an impact in college basketball. If Pope wants an elite X’s and O’s thinker to help build the program, Messina would be an inspired choice.
4. Oliver Winterbone – The Rising NBA Executive with SEC Ties
Currently a player development executive for the Oklahoma City Thunder, Oliver Winterbone has experience working with both college and pro athletes. He was on staff at Florida for four years, meaning he understands the SEC landscape and college recruiting while also knowing what it takes to develop talent for the NBA.
Winterbone could be an ideal fit if Kentucky wants someone who blends the NBA’s front-office structure with college basketball expertise. He wouldn’t bring the star power of a Pitino or Bird, but he might be one of the most practical hires available.
5. Austin Ainge – The NBA Front-Office Pro with a BYU Connection
Austin Ainge is currently an assistant GM for the Boston Celtics, working under Brad Stevens. He also has deep ties to Mark Pope, as he is the son of Danny Ainge, a BYU legend. That connection could help build immediate trust between Pope and a GM, which is crucial in this evolving college basketball landscape.
Ainge has spent years in the NBA scouting and developing talent, and his experience in one of the most successful front offices in the league would be invaluable to Kentucky. His name might not be as big as some others, but his connections, basketball mind, and executive experience make him a strong candidate.
6. Jamal Mashburn – The Kentucky Legend with Business Savvy
A former Kentucky star and longtime NBA player, Jamal Mashburn has built a successful career in business after basketball. He owns multiple franchises and has proven his ability to manage assets and investments, which could translate well into overseeing Kentucky’s NIL and roster construction strategies.
Mashburn understands what it takes to be a Wildcat, has NBA connections, and knows the business side of things better than almost anyone on this list. He could bring a player’s perspective to the front office while helping Kentucky navigate the new era of college basketball.
Final Thoughts: Which Direction Will Kentucky Go?
With college sports moving toward a professional model, hiring a GM will soon be as common as hiring an assistant coach. Kentucky has no shortage of elite options, from legendary figures like Pitino and Bird to NBA front-office minds like Ainge and Winterbone.
The biggest factor will be what Mark Pope wants in a GM. Does he want someone with deep recruiting ties? Someone who knows the NBA inside and out? Or a big-name hire that excites the fanbase?
Regardless of the choice, one thing is clear: the era of college basketball being run like the pros is here, and Kentucky is in a position to set the standard.