Photo by Rod Aydelotte/Associated Press

Five years ago Freddy Gillespie sat in his freshman dorm room at Carleton College, preparing to face Bethany Lutheran in what would be his collegiate basketball debut the next night. Gillespie would come off the bench to log 15 minutes for the Knights in their season opener, finishing with six points, five rebounds and three assists. On paper, an unremarkable performance. 

But for the lengthy big-man from East Ridge High School, his career would go on to be anything but unremarkable. Standing at 6-foot-9, with arms like wings and an eye catching vertical leap, Gillespie was a physical force unimaginable on a Division III basketball court. And while a Division III court may have been the starting point for Gillespie’s college career, it would not be his final destination.

Gillespie began playing the game of basketball later than most, not starting until the 8th grade. His high school years were plagued with injuries, tearing his ACL and twice breaking his ankle, limiting his exposure as a prep hoops prospect. Without much playing experience or skill, the then senior Gillespie set his sights on an academically focused school to attend after graduation, with the only schools recruiting him being local Division III institutions. Gillespie decided to play for Carleton College, looking to salvage a career that had barely begun in a rural Minnesotan town known more for its cereal than its basketball.

Despite his size, strength and obvious potential to be the best basketball player to ever step foot in Carleton’s West Gym, Gillespie would ride the bench for most of his freshman year. He broke his way into the starting lineup in his sophomore campaign, with stats good enough to earn him Second-Team All Conference. His sophomore highlights are jaw dropping, pinning his opponents shots off the glass with ease and throwing down put back dunks like you’d see in a video game.

After his sophomore season, the story goes that Gillespie was with his roommate watching the University of North Carolina Tarheels play in the NCAA tournament when he had an epiphany that he himself was capable of playing at the Division I level like the players he was watching on TV. I’m sure that for the next few days, Gillespie would lie awake at night, his legs hanging off the end of his twin bed, unable to escape the thought of leaving Northfield to pursue playing college basketball at a school like UNC.

Six months later, that’s exactly what Gillespie did, transferring to Baylor University as a walk-on after connecting with their assistant coach, a Minnesota native. Gillespie would redshirt his first year in Waco, working to develop his skills for a chance to compete at a level even his own Baylor teammates and coaches first thought he may never reach. But like Gillespie had done his entire career, he surprised everyone but himself, becoming the team’s starting center the following season.

This Baylor team was no average squad either, earning the No. 1 rank in the country for much of the 2018-2019 season. In just under two years, Gillespie had gone from playing in front of a few dozen Carls after poli-sci class to catching alley-oops in sold out Big-12 arenas. 

Gillespie never stopped improving, earning the Big-12’s Most Improved Player award the following year, while also nabbing a spot on conference’s all-defensive team.

Today, Gillespie is preparing for the NBA Draft, hoping to be one of the 60 most talented amateur basketball players in the world to be selected. Gillespie, who just only a few years ago was trying to find a way off Carleton’s bench, now has a chance to play against some of the greatest players the game has ever seen. It’s a story as heartwarming as it is unlikely, and it’s not over yet.

The draft takes place on Oct. 22, and even if Gillespie isn’t taken in the second round, he will likely be given the chance to sign with a team as an undrafted free agent for a team in the G-League, the NBA’s developmental system. He will look to follow in the footsteps of players like Duncan Robinson and Alex Caruso, both young talents who began their careers in the G-League and most recently competed against each other in the NBA Finals, each in the starting lineup of their respective franchise. Robinson is a fellow DIII alum like Gillespie, transferring from Williams College to the University of Michigan, drafted with the 55th pick in the 2018 NBA Draft.

Beyond all else, Gillespie’s story is emblematic of what it means to chase a dream. For most of us, our talents don’t stand out like the wingspan of a 7-footer in a brightly lit basketball gym. Our potential isn’t measured in rebounds on a stat sheet, or shot blocking presence in the paint. But nonetheless, we all have ambitions. And I’m willing to bet that almost every person has had their Freddie Gillespie moment, seeing someone else living their dream, with the same thought: “That could be me.”

At Carleton, Gillespie met his basketball ceiling fairly quickly. Understandably, the rigorous academic schedule of a prestigious liberal arts school paired with the coaching staff of a Division III athletic program isn’t known to produce NBA skill sets. If Gillespie had stayed at Carleton, who knows where he would have ended up.

We like to think that success is dependent on internal drive, and the intrinsic motivation to be great. When in reality, it’s more about surrounding yourself with the right environment, and finding some luck along the way. The lesson we should take away from Gillespie’s career is not that ceilings don’t exist, but that they are impermanent. Sometimes the hardest part of reaching your destination is finding the right path, and we often have more to lose by staying put than chasing the impossible.