If he wanted to win, he would've started more locally, because it's a known fact that Dedham people are crazy when it comes to local politics, and if he were a good select(wo)man they would all come out to vote for him. The problem there is, of course, that he wouldn't be a good select(wo)man.
Starting out running for Congress is dumb. People need to know you first.
Lynch was a state rep and a state senator first.
Ayanna Pressley, the lady who actually did unseat a Congressman? She was a Boston city councilor for nine years and the majority of people in her district live in Boston.