| Mark Waldron | 1996-1999 | Grew National division from 4 teams to 8 teams. |
| Tom Comparato | 2000-2002 | By-laws were created and EMASS became a formal organization in 2001. The first board of EMASS was directed by Tom Comparator. Paul Rosenbaum was Vice- Commissioner, John Stewart managed recruitment, Gerry Yaffe was in charge of equipment and Ralph Mosher was Treasurer. Many debates evolved to balance these teams. Paid umpires were introduced and the “liveliness” of the ball was assessed to address safety concerns. The annual awards banquet was introduced and originally held at the Officer’s Club at Hanscomb AFB. Golf tournaments and invitational softball tournaments were initiated to encourage interaction among the EMASS community. Finally, EMASS started its player evaluation process by managers to improve balanced team assignment in the next year. |
| Jerry Levin | 2003-2004 | Grew National division and American division to 6 teams each. |
| Stu Gray | 2005-2010 | By 2005 season there was a total of 246 assigned to 18 teams. Fifty of these players were in the Tuesday league only; 164 played exclusively in one of the two Saturday divisions; and 30 played in both Tuesday and Saturday leagues. The median age of all players was 61. The median in the Tuesday league was 66; with an average age of 60 in the American division and 63 in the National division. Overall, there were 93 players in the age range 55-59, 140 players in the age range 60-69, and 29 players age 70 and older. |
| Steve Goldstein | 2011-2012 | Started the Metro division. Moved all divisions to competitively balanced teams. |
| Jim Boice | 2013-2014 | Grew Metro division to 6 teams. |
| Rob Mitchell | 2015-2019 | The Pacific Division was established, the 20-Year Awards and Courage Awards were started. We reinvigorated a marketing and recruitment campaign that brought in over 100 new members to EMASS. David Ortiz made an appearance as a pinch hitter in a Metro game, and a new website was launched. Membership hit 400+ |
| Walker Royce | 2020 -2023 | Grew the league to almost 500 members, 40 teams, and 6 divisions. Walker created a management workshop to capture the culture of senior softball: Community, Sportsmanship and Competition…in that order. He rebuilt the EMASS website on TeamSideline to integrate and automate registration, enrollment, scheduling, scoring, rostering and finance. EMASS flourished during COVID (2020-21). Documented all the board roles, responsibilities, policies and procedures, and transitioned board meetings to Zoom. |