Profile: Cuff Whittemore

Overview:

Cuff Whittemore was a Black and possibly Native American soldier who fought in the Battle of Lexington and Concord and the Battle of Bunker Hill. He served in the Menotomy Minute Company and later in the Continental Army until 1782. Born in Menotomy (now part of Arlington and Cambridge, Massachusetts), Whittemore was legally free but lived in a condition often described as “unfree,” meaning that the racial caste system prevented him from living as independently as he otherwise could have.

He joined a respected minute company, showing skill and commitment. At Bunker Hill, he fought bravely in the redoubt and reportedly left the battlefield with a British officer’s sword--a trophy--which a few days later he sold. Later, during the Battle of Saratoga, he was captured but made a daring escape. After the war, he lived a hard life, working day labor jobs and applying for a pension in his later years.

Quick Facts:

• Born ca. 1751

• Born in Menotomy, Massachusetts (modern Arlington/Cambridge area)

• Of African and possibly Native American heritage

• Legally free, but lived in a dependent “unfree” social position

• Served in the Menotomy Minute Company

• Fought in Lexington and Concord and Bunker Hill

• Continued service in the Continental Army until 1782

• Captured at Saratoga and later escaped

• Worked as a day laborer after the war

• Applied for a veteran’s pension in 1818

• Died in 1826 in Charlestown, Massachusetts

Why This Story Matters:

Cuff Whittemore’s story challenges common ideas about who fought for American independence. He was not wealthy or powerful, yet he played a direct role in key battles. His service shows that Black and mixed-heritage men were part of the nation’s founding, even when they faced social limits and unequal treatment.

Whittemore’s life also reveals a gap between freedom and reality. He was legally free, but still struggled for stability and respect. His pension application shows how veterans like him were often left without basic support. By studying Whittemore, we better understand how race and social status shaped both opportunity and recognition in early America—and how many important stories were left out.

Legacy:

Cuff Whittemore’s legacy lives in the questions his life raises. He fought for freedom but did not fully experience it himself. His story reminds us that the American Revolution included people of many backgrounds, even if history books often focus on white leaders.

Today, Whittemore represents the many soldiers whose names were nearly lost. His pension records and local histories help restore his place in the story. By remembering him, we honor not just one man, but a larger truth: the nation was built by people whose contributions were not always recognized or rewarded.

Whittemore’s story does not appear in major films, but it fits powerfully into stories about the Revolutionary War. His experience could be compared to scenes in films like Glory, which show Black soldiers fighting bravely while facing inequality. A film about Whittemore would highlight both battlefield courage and the struggle for dignity afterward. His escape at Saratoga and his actions at Bunker Hill offer strong, dramatic moments. Just as important, his later life would show the cost of war and how some veterans were forgotten.

Discussion Questions:

1. If Cuff Whittemore had never been recorded in pension papers or local histories, what would we lose in our understanding of the American Revolution—and how does the absence of people like him shape the story we tell about the nation’s founding? 

2. What does it mean to be legally free but still lack power, stability, or opportunity in society?

3. If each generation writes current history based on what it has been taught to believe is true, how might leaving out people like Cuff Whittemore shape not only our understanding of the past, but also influence what we value and record in the future?

Reflection Prompt:

1. How might Cuff Whittemore’s life have been different if he had been born white and wealthy, and what does that comparison reveal about the impacts of race and social class?  Do they matter today?  Explain. 

Sources & Further Reading:

Sources:

1. “Cuff Whittemore (Cartwright/De Carteret).” National Park Service, U.S. Department of the Interior. 

2. Cuff Whittemore. Revolutionary War Pension Application. Document. Record Group 15, National Archives. 

3. “The Battle of Lexington April 1775.” Amos Doolittle. 1940–1950. Prints and Photographs Division, Library of Congress. 

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