Hepburn grew up in Omaha, Nebraska, and attended Bellevue West High School. A 6-foot-1-inch (1.85m)point guard, he averaged 15.9 points, 8.3 assists, 5.1 rebounds and 3.8 steals per game as a senior as Bellevue West appeared in the Class A state title. He guided Bellevue West to a Class A state title as a junior averaging 17.1 points, 6.5 assists, 4.6 rebounds and 3.1 steals per game.[citation needed] As a sophomore, Hepburn averaged 18.3 points, 5.0 assists, 5.1 rebounds and 3.4 steals per game.[1] Hepburn won the 2020 Nebraska Mr. Basketball Gatorade Player of the Year.[2]
Hepburn became the first true freshman to start the season opener since Devin Harris in 2001.[4] He went on to score 13 points in his first career game against St. Francis.[5] Hepburn banked in a tiebreaking 3-pointer with 1.5 seconds left against #8 ranked Purdue, giving the Badgers a share of the Big Ten regular-season title.[6] Hepburn was able to profit in the newly implemented NIL after the game-winning shot against Purdue with merchandise named "The Chucky Special".[7] After the regular season, Hepburn was named to the Big Ten All–Freshman Team.[8]
Sophomore season
Hepburn was asked to take on a larger role in his second season at Wisconsin after Johnny Davis was selected 10th overall by the Washington Wizards.[citation needed] Hepburn started all 35 games and was the Badgers leading scorer (12.2 points per game), 3-point percentage (.405), assists (2.8 APG) and steals (1.5 SPG).[citation needed] The team struggled with injuries midway through the season and Wisconsin missed the NCAA tournament. Following the conclusion of the regular season, Hepburn was named an All–Big Ten honorable mention selection.[9] The Badgers accepted an invitation to the NIT where Hepburn scored a career-high 27 points in a second round victory against Liberty.[10]
Junior season
Hepburn came into his junior season and has thrived in the role of facilitator and defender.[11] The previous season, he was looked at by his teammates as the "go to guy" to score late in shot clock or late in games.[11] With the additions of scorers AJ Storr and freshman John Blackwell, Hepburn has been able to refine other parts of his game.[11] Evidence of this is Chucky has put up his best assist to turnover ratio of his career and uptick in steals.[11] Following the completion of the regular season, Hepburn was named All-Big Ten honorable mention by the coaches and named to the All-Defensive Team.[12]
Louisville
Senior season
On April 25, 2024, Hepburn announced he would be transferring to Louisville.[13][14] Hepburn scored a career high 37 points against Pittsburgh on March 1, 2025. He was named ACC player of the week for the second time during the 2024-25 season.[15]
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