Escaping one's familial upbringing is easier said than done:
Despite my not liking The Town overall, as a film, this:
"
No matter how much you change, you still have to pay the price for the things you've done. I have a long road. But I know I'll see you again, this side or the other."
indicates at least a couple of things:
A) Since Doug, like his friends/partners in crime, had also perpetrated violencing by stealing from, robbing, beating up and otherwise injuring innocent people and putting their lives at risk, he, like his friends, paid a rather heavy price for his actions and behaviors, especially when he acted like a vigilante, went back to Charlestown, took the law into his own hands, and killed Fergie and Rusty in their own flower shop. Sure, Doug's friends, also perpetrators of violence, and were from similar family backgrounds ( i. e. gangsterism, etc.), they paid for it with their lives. Doug, on the other hand, paid for his having been a perpetrator of violence: Losing the woman he loved (and yet exploited), having to leave Boston, flee to Florida, and to hide out, and hope the Feds wouldn't find him. Doug will be looking over his shoulder for the rest of his life, and he'd never get accepted into another country, either.
B) At some level, despite not being a very nice or sympathetic parson, realized the possibility of his eventually being found and caught, perhaps violently, by the FBI, and either being forced to stand trial for and be charged with his crimes and end up serving a life-time sentence in a Federal penitentiary (for both Federal offenses (which bank and armored truck robberies are.), and first-degree murder (deliberately killing Fergie and Rusty), on top of all that.
C) The phrase "I know I'll see you again, this side or the other" is a euphemistic way of saying that they cannot ever meet again.
Having said all of the above, Doug never really did escape his familial upbringing. He'd blown the opportunity to be a pro Ice Hockey player through arrogance, insolence, cockiness and stupidity. He ended up following in his father's footsteps and entering into a life of crime. Doug skipped town for Florida without Claire, for good reason: Either she'd end up in big trouble if the Feds found her and Doug where they were hiding out, or Doug could either become abusive and nasty to Claire, who could very well end up on government assistance to support herself, especially if they'd had any kids together. share