Emmanuel Leutze’s 1851 painting is iconic. You know the one. George Washington stands heroically in a boat, looking toward the Jersey shore, while his men huddle against the freezing spray of the Delaware River. It’s the quintessential image of American grit. But if you look closely at the figure rowing right at Washington’s knee, you’ll see a man of African descent. For a long time, people just assumed this was artistic license or a "token" inclusion by a German-American painter with abolitionist leanings.
History is actually much noisier than that.
The truth is that the crossing the Delaware black man wasn’t just one person, and he wasn't a myth. While Leutze likely used the figure to represent the broader contribution of Black soldiers in the Continental Army, we have real names, real pension records, and real stories that place Black men in those boats on that miserable, icy night of December 25, 1776. It wasn't just about one guy. It was about a significant percentage of the fighting force that most history books ignored for two centuries.
The Man in the Painting: Prince Whipple
If you ask a historian who the specific man in the painting is supposed to be, the name Prince Whipple usually tops the list. Whipple was an African-born man who had been enslaved by William Whipple, a signer of the Declaration of Independence from New Hampshire.
Whipple’s story is incredible. He was reportedly sent from Africa to be educated but was sold into slavery in Baltimore instead. By the time the Revolution rolled around, he was acting as a bodyguard and aide to General Whipple. Legend says he was there at the Delaware.
Here’s where it gets a bit messy.
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Modern research by historians like J.L. Bell suggests that Prince Whipple might actually have been in Baltimore with his master at the exact time Washington was crossing the Delaware. It’s a bummer for the clean narrative, right? But Prince Whipple did participate in the Saratoga campaign later. He was a real veteran. He even signed a 1779 petition to the New Hampshire legislature asking for the "natural right to freedoms." He was a hero, even if he might not have been in that specific boat on that specific Christmas.
So why is he in the painting? Leutze was painting in the mid-19th century, right as the debate over slavery was tearing the U.S. apart. He wanted to show that Black men were foundational to the country’s birth. Even if the timeline for Prince was slightly off, the symbolism was 100% grounded in reality. Black men were everywhere in the integrated units of the early war.
Oliver Cromwell: The Vet Who Was Actually There
While the "Prince Whipple" attribution is debated, we have much stronger evidence for a man named Oliver Cromwell.
Cromwell was a Black soldier from New Jersey. He served in the Second New Jersey Regiment. Unlike some of the more legendary tales, Cromwell’s service is backed up by cold, hard paperwork. He served for nearly seven years. He saw action at Trenton, Princeton, Brandywine, Monmouth, and Yorktown.
He stayed in the fight.
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When he applied for his pension, he had his discharge papers signed by George Washington himself. Imagine that. Carrying around a piece of paper signed by the Commander-in-Chief. Neighbors and local officials in Burlington County, New Jersey, knew him as a veteran of the "celebrated crossing." He lived to be nearly 100 years old, dying in 1853. He was a local celebrity. He was the living embodiment of the crossing the Delaware black man that the painting tried to capture.
The Marblehead Mariners: The Secret Weapon
We can't talk about the crossing without talking about the "Glover’s Regiment." These were the guys from Marblehead, Massachusetts.
They were essentially a bunch of tough-as-nails fishermen and sailors. They knew how to handle a boat in a storm, which was the only reason the crossing didn't end in a mass drowning. The 14th Continental Regiment was one of the most diverse units in the entire army. It was fully integrated.
Think about the visual.
You’ve got white fishermen, Black sailors, and Native American mariners all rowing together in the dark. Without their specific maritime skills, Washington’s army never makes it to the other side. The "Black man" in the boat represents these anonymous heroes who quite literally carried the Revolution on their backs across the ice.
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Why Does This Matter in 2026?
Honestly, it’s about accuracy. For a long time, the American Revolution was painted as a very "white" event. But the Continental Army was surprisingly integrated until 1775, and then again out of necessity as the war dragged on.
By the end of the war, about 5% to 10% of the Continental forces were men of color. In a world where we’re constantly looking for "untold stories," this one has been sitting in plain sight on the walls of the Metropolitan Museum of Art for over 150 years.
The Political Reality
It’s worth noting that these men were fighting for a country that didn't yet recognize their humanity. Some were promised freedom in exchange for service. Others were fighting alongside their enslavers. It’s a complicated, sometimes uncomfortable layer of the story.
When you see the crossing the Delaware black man, you aren't just seeing a soldier. You're seeing someone fighting for a "liberty" that he wasn't even sure he would be allowed to have. That takes a specific kind of courage.
How We Know What We Know
Historians like William C. Nell (who was one of the first Black historians in the 1850s) and modern researchers like those at the Museum of the American Revolution have done the heavy lifting. They’ve dug through:
- Pension records: These are the gold mine. They often include personal testimonies of where a soldier was on a specific night.
- Muster rolls: These lists show who was present for duty.
- Newspaper obituaries: Back in the 1800s, being a "Revolutionary War Veteran" was a massive deal, and obituaries for men like Oliver Cromwell proudly listed their service.
Misconceptions to Toss Out
- "It was just one guy." Nope. Multiple Black soldiers were in the different units crossing that night.
- "The painting is a lie." Not exactly. It's a "historical reimagining." It captures the truth of the army's diversity, even if it fudges the specific faces.
- "They were all servants." Many were enlisted soldiers who carried muskets and fought in the front lines at the Battle of Trenton the next morning.
Actionable Steps for History Buffs
If you want to get closer to the real story of the crossing the Delaware black man, you don't have to just stare at a painting. You can actually trace these lives.
- Visit Washington Crossing State Park: They have specific markers and educational programs that highlight the diverse makeup of the troops.
- Search the Fold3 Database: If you're into genealogy, you can look up Revolutionary War pension files. Search for names like Oliver Cromwell or search by regiment (like the 14th Continental).
- Read "Black Patriots and Loyalists" by Alan Gilbert: This gives a deep, academic yet readable look at why these men fought and what happened to them after the war.
- Check out the Museum of the American Revolution in Philadelphia: They have incredible exhibits on the "forgotten" soldiers of the war, including interactive displays that track the movements of specific Black regiments.
The guy in the boat isn't a mystery anymore. He's a reminder that the American story was a group project from day one. Next time you see that painting, don't just look at Washington. Look at the men with the oars. That’s where the real work was happening.