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Derek Bolingbroke

Derek Bolingbroke

Derek joined the YMCA as the Programme Director of Little League in August 2020, having been in Cayman for 14+ years. Derek has a unique background in the entertainment and hospitality industries. Originally from Ontario, Canada Derek has always had a passion for sports, played rep baseball growing up and has his level three umpiring certificate with over 6 years’ experience behind the plate. Derek also has over ten years’ experience coaching youth track and field teams, most recently with the 345 Athletic club.


Although unfortunately a Toronto Blue Jays fan, Derek is passionate about youth development. Youth sports was a centre point in his childhood, and he jumped at the opportunity to continue to contribute to the development of young athletes in Cayman. In his role as Little League Programme Director, Derek is responsible for providing leadership and direction for both Little League and softball programmes. With responsibility for overall league management, Derek will work closely with staff and volunteers to ensure a safe, high quality, and family-friendly environment for all players and guests at the Field of Dreams. Derek looks forward to investing his efforts into player development, engaging and supporting volunteers, facility enhancements, and ensuring the long-term success of Little League.


Derek once had aspirations of being a sports broadcaster, and you may have heard him weekday mornings on the air-waves of Cayman as a morning show host with 106.1 FM. Around his full-time role with Little League, Derek will maintain a part-time role with the radio for a few hours a week. If you hear him on the radio while you are having a conversation with him, don’t’ be too alarmed!


Fun Fact: Derek’s great grandfather ran the city of Toronto baseball leagues for several years…it must be in his genes!

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