What Freedom Meant to Prince Whipple, The Black Revolutionary Soldier Famous for Rowing Across the Delaware

Captain Whipple called the older of the boys “Prince,” which was probably a callous joke on his royal pedigree. The other boy was given the common slave name “Cuffee.” Both lived and worked in Whipple’s house and stable.

When the revolution advanced to the point that patriots began setting up shadow governments, Whipple became a member of New Hampshire’s first independent assembly. He attended the sessions in Exeter accompanied by Prince, who had grown into an imposing strong man of twenty-five. When the assembly tapped Whipple to represent the state in Philadelphia, he rode south with Prince as his squire and personal servant. When the Continental Congress slowly lurched toward declaring independence, Whipple was one of the firebrands who never wavered from the course and earned the enduring respect of both John Adams and Thomas Jefferson. As the delegates to the Continental Congress assembled that summer of 1776, Whipple wrote his friend John Langdon on June 24, 1776, with exciting news: “Next Monday being the 1st of July, the grand question is to be debated, and I believe determined unanimously. May God unite our hearts in all things that tend to the well-being of the rising empire.” Whipple did not sign the Declaration of Independence with Hancock’s flair but scratched his dignified signature with the other patriots on that vellum. Whipple was not the only signer who had been a slave trader.  John Hancock’s partner in his Boston merchant house, James Rowe, also trafficked in humans.

Some weeks later Whipple was commissioned into Continental Army with the rank of captain. This required Prince to also enter the nation’s service but without formal rank or place in the army as the patriot cause then recognized only white soldiers. Whipple and Prince didn’t face battle at this time as they fled with the rest of the skeletal American government to Baltimore when the Redcoats seized Philadelphia.

On Christmas Eve of 1776, Whipple and Prince crossed the Delaware with General George Washington’s army to conduct a surprise attack on the British flank. The details of their actions during this battle are lost. The next year, Captain Whipple was given command of New Hampshire’s First Brigade and ordered to march west to meet Burgoyne’s redcoats. As he had done hundreds of times Whipple charged Prince with attending their horses and retired, but the next morning found the work still undone. According to Portsmouth’s local newspaper editor at the time, Charles Brewster, this led to the following exchange:

Prince appeared sulky and in ill humor and his master upbraided him for his misconduct.

“Master,” said Prince, “you are going to fight for your liberty, but I have none to fight for.”

“Prince,” replied his master, “behave like a man and do your duty, and from this hour you shall be free.”

Prince wanted no other incentive; he performed his duty like a man throughout the campaign, which ended in the surrender of Burgoyne, and from that day he was a freeman. 

This story is likely apocryphal on a number of grounds. First, according to the records of the New Hampshire Adjutant General, William and Prince served from Sept. 27, 1777, to Nov. 15, 1777. However, Prince clearly was not free in 1779, two years after he supposedly was promised his freedom, because he was one of nineteen black men who that year petitioned the New Hampshire Assembly for their freedom.

These men, describing themselves as “natives of Africa, now forcibly detained in slavery, in said state,” humbly but directly asked for some legislation by which “we may regain our liberty and be ranked in the class of free agents, and that the name of slave may no more be heard in a land gloriously contending for the sweets of freedom.” Prince and the other enslaved men had no fondness for their fetters and felt acutely the contradiction between American ideals and their condition. They were, they said, “born free to a country, where (tho’ knowledge, christianity and freedom, are their boast) they are compelled, and their unhappy posterity, to drag on their lives in miserable servitude.”

They rested their argument on many solid rocks of antislavery argument. On the grounds of natural law: “Nature gave them life and freedom, upon terms of the most perfect equality with other men; that freedom is an inherent right of the human species, not to be surrendered, but by consent, for the sake of social life.” On the grounds of religion, they objected that their enslavement was not Christian: “Is it from the sacred volumes of christianity? There we believe it not to be found!” On the grounds of the principle of property: “our present masters, will not be sufferers by our liberation, as we have most of us spent our whole strength and the prime of our lives in their service.”

New Hampshire’s legislature read and tabled this petition at their session the following year. When Prince jumped the broom with his bride Dinah Chase, a free black woman from nearby New Castle, he did so as another man’s property. Dinah’s legal owner signed her manumission papers on the day of her wedding, but it would not be until 1784, three years later, that William Whipple would finally put his famous signature to another declaration of independence, that most dear to Prince, his own manumission.

But even this act was not quite a fulfillment of some wartime promise. Whipple chose to execute his manumission when his claim to human property was shaken and made uncertain by legal currents roiling New England. To the south, the Massachusetts Superior Court had essentially rendered slave property unenforceable in that state’s courts in a series of rulings (citing the freedom suit of Elizabeth Freeman) that involved Quok Walker, a man who stole himself away from his master and was able to defend his self-possession in court. New Hampshire had just drafted a constitution and its bill of rights was sufficiently broad to leave property in human beings on dubious legal ground. 

William Whipple’s long delay in fulfilling his promise of freedom to the man who had loyally served him and his cause could be seen as an act of hypocrisy. Whipple was certainly knowledgeable of the legal decisions that were shaking the foundations of Yankee slavery in Massachusetts and elsewhere. He served as a justice in the New Hampshire Superior Court from 1782 until his death in 1785. Such an interpretation would be consistent with the way other American founders, like Washington, Jefferson, and Madison, have been reframed in recent years. But such conclusions are too easy because it was quite possible within the worldview of a wealthy and powerful white American, which Whipple undoubtedly was, to both hate slavery yet remain reluctant to free any particular enslaved person.

There is plenty of evidence that William Whipple sincerely wished slavery would die a swift death in the new republic. When the dashing young patriot and aide-de-camp of General Washington, John Laurens, proposed raising a regiment of enslaved men in South Carolina on the promise of their freedom, Whipple was elated and wrote a friend, “The last accots from S. Carolina were favorable. A recommendation is gone thither for raising some regiments of Blacks. This will I suppose lay a foundation for the emancipation of those poor wretches in the Country, & I hope be the means of dispensing the Blessings of freedom to all the Human Race in America.” Like Benjamin Franklin, Whipple most likely viewed slavery as a force that endangered the dream of America becoming a land filled with white immigrants. During the war, Whipple expressed his vision of America as a land peopled by (presumably white) emigrants: “The prospect of laying a foundation of liberty and happiness for posterity, and securing an asylum for all who wish to enjoy those blessings, is an object, in my opinion, sufficient to raise the mind above every misfortune.” Many, maybe even most, patriots opposed slavery not because they deeply sympathized with those chained, but because they viewed slavery as being responsible for growing the black population which they believed would always be a rebellious and criminal element of society.

Despite being cheated of years of freedom by the man who claimed to own him, Prince Whipple chose to live in his shadow, spending the rest of his life living in a small house in William Whipple’s backyard where he and his wife Dinah raised six children. His decision raises eyebrows today. Why would a man remain loyal to another who dehumanized and ultimately betrayed him? The answer lies not in Prince Whipple’s misplaced feelings of loyalty, but instead reveals the overwhelming danger and oppression that faced “free” black people in supposedly “free” northern states.

Prince Whipple would have heard of many African American veterans like himself who were taken back into the ownership of a white man after they took off their uniform. The full story of the numbers and experiences of black Revolutionary War veterans forced back into slavery has never been told—quite the opposite—as their experiences don’t fit comfortably within the heroic storyline of the plucky patriots fighting for liberty. Evidence for the ongoing suppression of the truth is that the writers closest to these events were more aware of them and knowledge of this tragedy seems to have faded as the centuries passed.

In 1842, an ancient white veteran of the Continental Army, identified only as Dr. Harris, spoke before the Congregational and Presbyterian Anti-Slavery Society, at Francestown, New Hampshire and wondered,

Now, the war is over, our freedom is gained—what is to be done with these colored soldiers, who have shed their best blood in its defence? Must they be sent off out of the country, because they are black? or must they be sent back into slavery, now they have risked their lives and shed their blood to secure the freedom of their masters? I ask, what became of these noble colored soldiers? Many of them, I fear, were taken back to the South, and doomed to the fetter and the chain.

While the proportion of African American Revolutionary War soldiers who were dragged back into bondage cannot be precisely determined, it is clear that this danger was one that lurked in the fears of many, even in the North. Legislative hearings held in Rhode Island after the war established that at least two of the black men promised their freedom had been re-enslaved and taken to the South. A substantial number of lawsuits were lodged in state courts around the nation on behalf of black war veterans who had been falsely promised their freedom. These suits pointed to the tragic fact that black veterans could not protect themselves from re-enslavement. Rather, they depended on community networks in black neighborhoods in larger cities and the help of powerful white patrons to defend their freedom.  

Free black men and women in the early years of the American republic knew that what little freedom and property they had could be stolen in an instant. Their survival often depended upon cultivating the patronage and protection of powerful white men. Prince Whipple was painfully aware that the scope of his freedom did not extend beyond the ability of his namesake to intervene in the courts or with local officials on his behalf.

Freedom did bring new opportunities for Prince and Dinah, but it did not release them from the control of their former masters, who now assumed the role of their patrons. Prince and Dinah certainly understood the important social, economic, and legal protections that white patrons brought them. They could not enjoy these protections on their own, even with their freedom and a questionable claim to citizenship. They knew from the painful experiences of other African American families in New England, even of other black veterans of the Continental Army, that their ability to hold property, to remain a resident in their town, or even to keep their family together, depended on their maintaining a close personal relationship with a white man of position and influence.

Many accounts of Prince’s postwar life note that his former owner, William Whipple, granted Prince use of a “small corner patch” of the yard behind his house where he and his brother Cuffee erected a small house in which they, their spouses, and their children lived. Few note that in New England at this time it was common for black families to be “warned out” by town officials and forced to move west or to one of the larger cities in the region. None observe that it was also common for town officials to force black families to surrender their children to neighbors as “apprentices,” meaning that they would be worked as unpaid servants until they reached maturity. When Prince and his brother accepted William Whipple’s offer of settling their families in his backyard, they were also accepting his protection.

Prince and his brother Cuffee Whipple were technically free, but clearly dependent on their former master’s family. This situation was common in a world where freedom was a matter not so much grounded in law but in practice. Prince worked odd jobs, including some manner of dining service at a local ballroom, and was known as a jack-of-all-trades. Cuffee also worked as a servant, and earned additional money entertaining guests with his violin.

Most remarkably, Dinah taught black children, first out of their small home, and then more formally under the sponsorship of a white benevolent association, the “Ladies Charitable African Society.” Dinah’s school, like other black schools in New England, faced constant threat from those who believed the existence of such institutions would induce other black Americans to settle in the town. Dinah was still operating her school when Connecticut prosecuted Prudence Crandall, a white teacher, forcing her to close her school for black children in 1834 or the following year when a mob attacked and destroyed the Noyes Academy, an integrated school in Canaan, New Hampshire. Dinah’s ability to educate several generations of Portsmouth’s black children depended on her family’s subservient relationship with the leaders of the town.

But patronage had its limits. Later in life, in her seventies, after Prince, Cuffee, and Cuffee’s wife had all passed away, Dinah still lived in the little house she didn’t own in her husband’s former master’s garden. After William Whipple’s widow died in 1832 and the property was passed to her children, Dinah was moved to a house the heirs owned in a black neighborhood. Perhaps it is not unreasonable to speculate that even though social pressures were not enough to break the Whipple’s long-standing feelings of noble obligation to their former black servants, they were enough to shuffle them out of sight.

In 1851, the German artist Emanuel Leutze debuted his epic, life-sized painting “Washington Crossing the Delaware,” which quickly became one of the most iconic portraits of both the father of the nation and of the Revolutionary War. In that famous image, Washington stands tall over the soldiers rowing across the icy river, one of whom is a black man. Prominent historians still mistakenly believe that this man was Prince Whipple, an African American whose image was adopted as the emblem for all black soldiers of the Revolutionary War. 

It is now known that Leutze had probably never heard of Prince Whipple. Rather, he included the image of a black rower because Washington’s flatboat symbolized the American nation and Leutze strove to represent a variety of ethnic types to complete this metaphor. Additionally, Leutze was influenced by the much earlier depiction of Washington’s army’s crossing by Thomas Sully that also included a single black figure among those poised around the great general. Sully, painting his canvas in 1819, was much closer in time to the events depicted and knew that Washington was accompanied throughout the war by one of the men he enslaved, William Lee. Sully surely had seen John Trumbull’s portrait of Washington with Lee poised on horseback in a fantastical turban as he worked for him as a studio assistant. In the end, the figure of the black soldier drawing his oar was partly an artistic trope that Leutze was repeating rather than an attempt at historical accuracy. 

Nevertheless, soon after Leutze’s masterpiece appeared, several writers identified Prince Whipple as the rower. William C. Nell, a writer and assistant editor with Frederick Douglass’ newspapers, published Colored Patriots of the American Revolution in 1854 and wrote:

In the engravings of Washington crossing the Delaware . . . a colored soldier is seen, on horseback, quite prominent, near the Commander-in-Chief,–the same figure that, in other sketches, is seen pulling the stroke oar in that memorable crossing. This colored soldier was Prince Whipple, body-guard to Gen. Whipple, of New Hampshire, who was Aid to General Washington.

Curiously, Nell himself identified another black soldier who took part in that crossing, though he chose not to associate him with images of Washington on that occasion. In his book, Nell quotes a newspaper clipping about Oliver Cromwell, a black soldier who served with New Jersey’s Second Regiment. Cromwell fought battles from the beginning to the end of the war and even remembered seeing the last soldier fall at Yorktown. Like Prince Whipple, he also paddled across that frozen river and fought at Trenton. But because Prince was the property of a man Nell thought was close to Washington, he credited him with being the actual figure made iconic in paint. 

The debate over who was the man Leutze depicted in his masterpiece of Americana faded once Currier and Ives rendered the painting as a lithograph and it was republished in many of the illustrated magazines that rose to popularity in the Jim Crow era. Catering to white audiences, Currier and Ives chose to remove the black rower from the scene. Interest in the man so plainly visible in the actual canvas still hanging in New York’s Metropolitan Museum of Art only revived in the 1960s when the NAACP distributed newspaper features extolling the exploits of America’s black soldiers of the revolution. 

Emanuel Leutze depicted a black man carrying the father of the nation across the Delaware into battle for his nation’s freedom. Whether or not that man was in fact Prince Whipple, Prince metaphorically never stopped paddling that boat. America to him, and to men like him, was a land of freedom only as far as the powerful white man standing over them allowed.

 

Further Reading

Elliot Bostwick Davis, Thomas Sully: George Washington and the Passage of the Delaware (Boston: Museum of Fine Arts, 2016).

Karsten Fitz, “Commemorating Crispus Attucks: Visual Memory and the Representations of the Boston Massacre, 1770-1857,” Amerikastudien / American Studies, 50:3 (2005): 463-84.

William Lloyd Garrison, The Loyalty and Devotion of Colored Americans in the Revolution and War of 1812 (Boston: R. F. Wallcut, 1861). The quote by Dr. Harris appears on p. 6.

Glenn A. Knoblock, “Strong and Brave Fellows”: New Hampshire’s Black Soldiers and Sailors of the American Revolution, 1775-1784 (Jefferson, N.C.: McFarland & Co., 2003).

William C. Nell, Colored Patriots of the American Revolution (Boston: Robert F. Wallcut, 1855).

Mark J. Sammons & Valerie Cunningham, Black Portsmouth: Three Centuries of African-American Heritage (Lebanon, New Hampshire: University of New Hampshire Press, 2004), pp. 68-70, 93-94.

Natalie Spassky, American Paintings in the Metropolitan Museum of Art, vol. 2, ed. Kathleen Luhrs (New York: Metropolitan Museum of Art, 1985), 16-24.

Judith L. Van Buskirk, Standing in Their Own Light: African American Patriots in the American Revolution (Norman: Univ. of Oklahoma Press, 2017).

 

This article originally appeared in August 2024.

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Timothy Messer-Kruse is the author of Patriots’ Dilemma: White Abolitionism and Black Banishment in the Founding of the United States of America (Pluto Press).