Obama could share at least one experience with todays Winter Hill resident: the plague of parking tickets. When he left town in 1990 he left behind $400 in unpaid fines and late fees because of traffic violations in Cambridge and $72.63 in excise taxes and $45 in late penalties in Somerville. Those fines went unpaid for almost two decades until in 2007, a few months into his campaign, Obama paid the fines and cleared his name as a scofflaw.
Winter Hill is a slightly scary neighborhood. For a long time it was the home of the Irish mafia (not the Kennedys — that branch of the Irish mob lived in Brookline)http://www.concurringopinions.com/archives/2008/02/sharing_an_apar.html