Prince Whipple was born into a wealthy Royal African family. At the age of ten, his family sent him to America for an education. Before he arrived at the colonies he was shanghaied by the ship’s treacherous Captain and then forced into slavery. A ship Captain, William Whipple, a famous leader in New Hampshire purchased the young Prince. Prince then took on the surname of Whipple.
At the start of the Revolutionary War, William Whipple received a general commission under George Washington's command. An 1824 history book provides the details following William Whipple's promotion to general:
On his way to the Army, he told his servant [Prince] that if they should be called into action, the expected that he would behave like a man of courage and fight bravely for his country. Prince replied, "Sir, I have no inducement to fight, but if I had my liberty, I would endeavor to defend it to the last drop of my blood." The general freed him on the spot.
Prince Whipple served in the Army and fought in the Battle of Saratoga in 1777 and the Battle of Rhode Island in 1778. He directly attended General Washington and the general staff throughout the revolution, serving as a soldier and at the highest levels of honor.
He was with George Washington at the crossing of the Delaware River. In the picture painted in 1851, he is sitting at the bow of the boat working the oar. Sitting in front of Prince Whipple is Prince Estabrook, officially the first Black Patriot of the Revolutionary War on the Lexington Green when the first “shot heard around the world” was fired. .