The Jack O’Brien Achievement Award is presented annually to the MCSAO member school that has the most successful athletic program. The member school that wins the most MCSAO State Championships across all three seasons.  Winning this award shows an embodiment of hard work, dedication, sportsmanship, passion, and commitment to excellence in high school athletics.  This award recognizes the overall success and commitment to developing a high level of high school student athletes in all seasons.

The award is named after Jack O’Brien, Executive Director of the MCSAO from 2005 – 2014 and current Athletic Director at Prospect Hill Academy.  Jack was the founding member of the Massachusetts Charter School Basketball League (MCSBL) in 2002 which later became the MCSAO in 2005.

2022-2023- Excel Academy Charter School

2021-2022- Salem Academy Charter School

2020-2021- Salem Academy Charter School

2019-2020- Salem Academy Charter School (No spring athletics)

2018-2019- Salem Academy Charter School

2017-2018- Salem Academy Charter School

2016-2017- Community Charter School of Cambridge

2015-2016- Community Charter School of Cambridge

2013-2014- Foxborough Regional Charter School

2012-2013- Foxborough Regional Charter School

2011-2012- Boston Collegiate Charter School

2010-2011- Prospect Hill Academy