Have association officers who umpired a lot of games {who know every team character} to nominate some of the top picks from the league {max 6, preferably 2}. To be nominated, the trusted officers must select from a qualifying list of judgment criteria. Keep this poll secret. Then allow all asssociation members to vote by ranking finalist. Ex 1, 2, 3, and 4 where lowest tally wins or assigning points 1, 2, 3, and 4 where highest tally wins. The officers may elect their teams favorites like candidates for office, but then the membership selects the overall trophy winner and 2nd runnerup.
Suggested from lower echelon