Among the most recognizable symbols of the American Revolutionary War is the famous painting of General George Washington crossing the Delaware River on December 25, 1776. The scene immortalizes the daring nighttime crossing that led to the 3:00 a.m. surprise attack on Trenton, New Jersey, a turning point in the war. The men crossed the icy river in Durham boats, fighting exhaustion, freezing temperatures, and British opposition.
The iconic painting was created by Emanuel Leutze, born May 24, 1816, of German descent. One of the most debated mysteries of the artwork is the identity of the third man at the front of the boat. Historians have long speculated that this figure may represent Prince Whipple, an enslaved man from Portsmouth, New Hampshire.
Prince Whipple was born in Amabou, Ghana, and was brought to America aboard a cargo ship owned by William Whipple, a shipmaster who amassed wealth through participation in the Triangle Trade. Prince Whipple became the property of General William Whipple, who received his first military commission in 1777. Prince accompanied him as an enslaved servant during the war.
Prince Whipple reportedly challenged General Whipple on the contradiction between fighting for liberty while holding another man in bondage. General Whipple promised Prince his freedom if he continued his military service. At the conclusion of his service, Prince Whipple was freed.
More importantly, the Delaware Crossing portrait frames the vital contributions of men of color, both free and enslaved, whose involvement in the Revolution has often been overlooked.
The Boston Massacre
On March 5, 1770, events escalated in Boston, leading to what is now known as the Boston Massacre. The first man to fall was Crispus Attucks, a runaway enslaved man of African and Native descent. Standing 6 feet 2 inches tall, Attucks was a sailor, stevedore, and whaler who made his living on Boston’s docks. He lived hidden in plain sight for nearly 20 years.
Eyewitness testimony published after the massacre described Attucks as neither fully Black nor white, but of mixed ethnicity. His death made him the first martyr of the American Revolution.
Crispus Attucks is buried in Boston’s Granary Burying Ground, alongside Paul Revere and three signers of the Declaration of Independence:
- Samuel Adams
- John Hancock
- Robert Treat Paine
The Midnight Ride
Paul Revere was not alone on his famous midnight ride. Wentworth Cheswell, a free Black man, rode several times to alert patriot communities of British troop movements.
At just 22 years old, in 1768, Cheswell was elected town constable and later town messenger for the Committee of Safety, making him the first African American elected to public office in American history.
Historian Lepore recounts Cheswell’s ride during the British invasion on December 13, 1774, and his continued service. On April 18, 1775, the night before the Revolutionary War officially began, Cheswell rode north from Boston warning communities of the impending British attack.
That same night, Paul Revere rode west, spreading the warning, “The British are coming.” The Old North Church served as a signal tower, displaying lanterns—one if by land, two if by sea. On April 19, 1775, the Revolutionary War began.
Black Patriots of the Revolution
Salem Poor, born enslaved, purchased his freedom in 1769 and enlisted in May 1775. He fought at the Battle of Bunker Hill, where he is credited with mortally wounding British Lieutenant Colonel Abercrombie. Salem Poor was one of 30 African Americans who fought in that battle.
Peter Salem, born enslaved in Farmington, Massachusetts, was sold to Lawson Buckminster. When Buckminster became a Major in the Continental Army, Peter Salem was freed so he could enlist. He served as a minuteman and fought alongside other Black patriots, including Titus Coburn, at Bunker Hill.
Samuel Ashbow, a 29-year-old Mohegan, was one of four brothers who gave their lives in pursuit of freedom.
Seymour, enslaved by the brother of Aaron Burr, escaped and enlisted in the British Army under the promise of freedom. After capture, he was returned to his owner, Seymour Burr, who later agreed to free him if he gave up his British enlistment bounty and joined the Continental Army.
Cato Howe, a Plymouth native, was likely a free Black man who fought at Bunker Hill, Valley Forge, and crossed the Delaware with Washington on December 25, 1776. He marched in the New York campaign and through Princeton, Saratoga, and Monmouth.
It is highly probable that Cato Howe and Quamany (Quanony) Quash were present at Morristown, the Dey Mansion in Wayne, the encampment on Rifle Camp Road in West Paterson, and Monmouth Junction.
Prince Hall, born in 1735, was enslaved until adulthood. By 1770, he was free and literate. Hall encouraged enslaved and free Black men to join the colonial militia and believed Black Americans were foundational to the nation.
Quamany Quash, enslaved by Theophilus Cotton, a Son of Liberty from Plymouth, served at Boston, Trenton, Princeton, and Monmouth. He was freed in 1781 after serving in the Continental Army.
The First Rhode Island Regiment
The First Rhode Island Regiment was the first Black regiment in the Continental Army. Authorized on May 6, 1775, it served until 1783 and was one of the few units to serve throughout the entire war.
On February 14, the Rhode Island Assembly voted to allow every able-bodied Negro, Mulatto, or Indian to enlist. On November 12, 1778, enslaved men were allowed to serve in exchange for freedom. On January 1, 1781, the regiment was consolidated at West Point, New York, and later stationed in the Hudson Valley Neutral Zone.
George Washington and the “Fifth Column”
George Washington inherited enslaved people early in life and owned slaves for all 56 years of his life. At his death, he owned 317 enslaved people, all of whom he freed through his will.
Washington enforced physical punishment and dealt with widespread resistance at Mount Vernon, including runaways, arson, theft, sabotage, slowdowns, and feigned illness. His personal chef Hercules escaped successfully, as did Ona Judge, Martha Washington’s maid.
On June 15, 1775, Washington was appointed Commander-in-Chief. Initially, he excluded Black men from service, fearing a “fifth column.” After Lord Dunmore’s Proclamation on November 7, 1775, which promised freedom to enslaved people who joined the British, Washington reversed course by January 2, 1778, following recommendations from James Mitchell Varnum.
William “Billy” Lee
On May 3, 1768, Washington purchased two brothers, Will and Frank Lee, described as “mulatto.” Will—later known as William “Billy” Lee—became Washington’s valet and body servant throughout the Revolutionary War.
William Lee was present at Monmouth (1778) and Yorktown (1781) and accompanied Washington to Dey Mansion in 1780. He was the only enslaved person immediately freed by Washington’s will and received an annual pension of $30. William Lee died at Mount Vernon in 1828.
Picnic at the Passaic Falls
On July 10, 1778, General Washington picnicked at the Great Falls of the Passaic River with Marquis de Lafayette, Alexander Hamilton, James McHenry, and William “Billy” Lee. They shared cold ham, tongue, biscuits, spirits, and grog.
It was here that Alexander Hamilton envisioned America’s economic independence, powered by the Falls. Washington returned in 1780, and on October 22, 1780, he wrote to the Continental Congress seeking support for the war effort.
Short Summary (Integrity Preserved):
In a letter written at Headquarters at the Passaic Falls on October 22, 1780, George Washington explains that Congress has ordered an inquiry into Major General Horatio Gates and that he has appointed Major General Nathanael Greene to take command during the investigation. Washington strongly recommends Greene as a capable, brave, and resourceful leader and urges influential supporters to give him full cooperation, especially given the dire situation in the Southern states.
Washington then outlines the severe condition of the Continental Army, emphasizing the lack of money, supplies, clothing, and manpower. He warns that the war cannot continue without major reforms, calling for a new strategic plan, stable financing through loans and taxation, a permanent army, and stronger centralized authority in Congress. Without these changes, he cautions, the American cause risks failure despite continued sacrifice.