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Tobias Ceasar is the Director of Basketball Operations for Overwin Academy. He was the Athletic Director and Head Coach of the Prep basketball team from 9th grade up to post-grad at The Master's School in Simsbury, Connecticut. Tobias has had a good success rate at placing his student/athletes at four year institutions.

John Swetye is the Chief Operating Officer of Overwin Academy. He has owned and operated a television production company for the past 35 years including working for the past 15 years with NBC Sports on live productions. He has had a life-long love of basketball and has coached both of his sons since they were old enough to walk. He has experience coaching teams and players at the youth, high school, and college level. His son Zak is in the class of 2022 at Xavier University in Cincinnati and is on the men's basketball team. His son Zarek is in the class of 2021 at Darien High School in Darien, Connecticut and is on the boys basketball team.