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Charlestown’s most characteristic pastime had long been the reckless sport of “looping.” The young “looper” played by a rigid set of rules. First, he stole a car in downtown Boston. Then he roared into Charlestown, accelerating as he reached City Square, where the District 15 police station stood in a welter of bars, nightclubs, and pool halls. Often he had to take a turn around the square before the first policeman dashed for his patrol car or motorcycle. Then the chase was on: down Chelsea Street to Hayes Square, up the long slope of Bunker Hill Street to St. Francis de Sales’ Church at the crest, then down again, picking up speed, often to 70 or 80 miles per hour, until a screeching left into Sullivan Square took him onto Main Street, where, dodging the stanchions of the El, he roared into City Square again, completing the “loop.” All that remained was to ditch the car before the police caught up. Looping was an initiation rite, proof that a Townie had come of age. But it was something else as well: a challenge flung at authority, a middle finger raised to the powers that be. Before long, looping became a kind of civic spectacle, pitting the Town’s young heroes against the forces of law and order. Plans for a loop circulated well in advance. At the appointed hour, hundreds of men, women, and children gathered along Bunker Hill Street, awaiting the gladiators. When the stolen car came in sight, racing up the long hill, a cheer would rise from the spectators, followed by jeers for the pursuing policemen. The first recorded “loop” was performed in 1925 by a sixteen-year-old daredevil named Jimmy “Speed King” Murphy, but most renowned of all was “Shiner” Sheehan, the teenage son of a federal alcohol agent, whose exploits so electrified the Town that he drew round him a group of young acolytes. Membership in their “Speeders Club” was limited to those who could produce newspaper clippings showing they had bested the police.
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J. Anthony Lukas (Common Ground: A Turbulent Decade in the Lives of Three American Families (Pulitzer Prize Winner))