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While on an errand to Boston with Achilles Davenport, a teenage Connor witnessed a commotion near the Old State House. Achilles urged him to look closer, and he saw that the clash between the Regulars and citizens had been sparked by a small group of Templars, including Charles Lee and the boy's father, Haytham Kenway.
Connor followed one of Haytham’s Templar snipers to the rooftops and managed to assassinate him before he could fire into the crowd. Unfortunately, Charles Lee was in a vantage point across the street, and pulled the trigger, causing panic among the soldiers and citizens, resulting in the death of numerous innocents, in an event which came to be known as the Boston Massacre. Connor was accused of firing the first shot, making him notorious in the city.
In an effort to clear his name, Achilles directed him towards a Revolutionary named Samuel Adams. Adams showed Connor how to reduce notoriety by exploiting means of propaganda and tearing wanted posters from the streets. He also introduced the boy to the Freemason's tunnels beneath Boston, which allowed for faster travel in the city.