Jack Fleming, the first of his three siblings to attend MBS, was a member of the baseball team from freshman year through senior year, as well as a runner for the cross country team his sophomore, junior, and senior years, holding the title of captain on both teams his senior year. 
He was a pitcher (10-2) on the 2010 state championship team. 

He has been a member of the Crimson baseball coaching staff since 2019, having coached the middle school team, then the freshman and JV teams in the Upper School. He is honored to coach for the Crimson baseball program and be a part of its winning culture once again.