In the aftermath of the Boston Massacre, which occurred on March 5, 1770, tensions between British soldiers and the colonists in Boston reached a boiling point. The trial of Private Hugh Montgomery and Private Matthew Kilroy from the 29th Regiment of Foot was a significant moment in the legal proceedings that followed this violent event. Montgomery stood trial for the manslaughter of Crispus Attucks, an African American man and one of the first casualties of the massacre, while Kilroy faced similar charges for the death of Samuel Gray, a local rope maker. Both men were found guilty of manslaughter on December 5, 1770. The verdicts of guilty were reflective of the prevailing sentiments in a city increasingly hostile toward British rule. The proceedings were highly publicized and drew substantial community engagement as tensions in the colonies continued to escalate.

The legal outcomes highlighted the division between loyalist sentiments and those advocating for independence. The event intensified calls for justice and accountability of the British troops stationed in the colonies, thereby fueling revolutionary sentiments. The trials were conducted under considerable scrutiny, with Boston citizens rallying around the belief that the soldiers should be held to the same standards as civilians, emphasizing the emerging ideals of liberty and justice. Montgomery and Kilroy's cases were integral in shaping the legal landscape concerning military conduct and civilian relations, transforming to form a larger narrative within the quest for American independence.