My own opinion is that Jason and Red and Betsie Hollis are the three most influential people on the local league tennis scene and Freeman's exit will leave a big void for someone to fill. I'm not sure what will become of the teams he had planned for next year. Whatever 4.0 team he assembled would have been an odds-on favorite to take the city just based on past performance. I'm not sure if he ever would have been able to truly hang with the big boys in 4.5...we may never find that out.
From a personal standpoint, I had a great time playing on his team last year. His enthusiasm and passion reinvigorated me and was infectious. It's just a lot more fun to play on a team with someone who is really passionate about league, and the only other teammates I've had that were equally inspirational were Tuan Tran and Red Benzon. Playing league next year is just not gonna' be the same for me.