Kaleb attended Westerville South High School and played alongside older brother Andre.

He had seven points and four rebounds as the Wildcats beat Lima Senior High School 57–55 to claim the state title.

As a senior, Wesson averaged 22.4 points and 10.9 rebounds per game and shot 67 percent from the floor on a team that finished 19–6.

[2] Sources: After arriving at Ohio State, Wesson worked to get in better shape, losing weight by cutting out soda and juice.

[6] He missed three games and returned in time for a Big Ten Tournament matchup with Indiana, finishing with 17 points, 13 rebounds, three assists, three blocks and two steals in the 79–75 victory.

[10] After scoring 10 points and grabbing 11 rebounds in a 76–51 victory over Villanova, Wesson was named Big Ten player of the week on November 18.

[20] On September 9, 2021, Wesson signed with Hapoel Gilboa Galil of the Israeli Basketball Premier League.