July 24, 2008 — Though not nearly as scandalous as the Beverly Farms Horribles Parade, which made national headlines earlier this month by lampooning teen pregnancy, Edward J. O’Reilly’s float in neighboring Gloucester’s 4th of July parade raised a few eyebrows nonetheless.
O’Reilly, a criminal defense lawyer and first-ever Democratic challenger to U.S. Sen. John Kerry, enlisted a friend to rig a windsurfing board to the back of a truck. Blowing in the breeze was a sail with the word “Flip” on one side and “Flop” on the other, while a figure wearing a John Kerry mask and T-shirt balanced on the board.
“People were yelling at him, giving him the finger,” O’Reilly recalls a week after the parade. “It was great!”
That kind of over-the-top campaign stunt is typical for the Gloucester attorney, the unlikely opponent of the former presidential candidate. Stocky and intense beneath a shock of frizzy gray curls, 54-year-old O’Reilly is a virtual no-name who’s betting that Massachusetts Democrats are tired of Kerry — so tired, in fact, that they will vote for an outsider who has never held a statewide political office.
