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The only way to get most of the teams into such a tournament would be to do it early as part of the non-conference schedule (but this would mess up a team's non-conference schedule). Have the Post rank the top 8 teams in the area in early March and then do a "DC Classic" tournament in mid-March (if a team is committed to a Spring trip, then they are just left out). Play Round one on a Thursday, round two on a Saturday, and the Championship on a Sunday.
I'm fairly certain that the point of the tournament isn't necessarily to determine who the best team in the District is, but to give public schools a shot at the best private school team in the city. This year, the matchup was perfect. St. Albans was hands down the best private school team in the District and Wilson has been the top public school for over a decade.
One of the goals of the Classic is to garner interest in baseball by kids of the inner cities, I think that goal would be defeated if every year the game pitted St. Albans and St. Johns against each other, two schools that are 40 K a year that most inner city kids wouldn't care about anymore than a regular Nationals game.