History

The Real Mercenary Behind Sleepy Hollow’s Headless Horseman

October 27, 2022Mac Caltrider
The Headless Horseman Pursuing Ichabod Crane by John Quidor. Photo courtesy of Wikimedia Commons.

The Headless Horseman Pursuing Ichabod Crane by John Quidor. Photo courtesy of Wikimedia Commons.

The headless horseman needs little introduction. Perched atop a phantom steed, with his flowing black cape and jack-o’-lantern head, he is one of the most immediately recognizable figures in horror iconography.

Over the years, he has appeared in countless books, films, and television shows, and in various permutations, with recent examples including on-screen villains like Pumpkinhead, Sam from Trick ‘r Treat, and of course, Christopher Walken’s spike-toothed rendition of the phantom rider in Tim Burton’s Sleepy Hollow. Come every fall, you’ll start seeing his glowing orange face everywhere — on beer labels and bags of coffee, in candy commercials, and hanging out on creepily decorated lawns along with zombies, ghosts, and giant plastic spiders. He’s basically the Santa Claus of Halloween.

Disney Headless Horseman

The headless horseman as seen in Disney's The Adventures of Ichabod and Mr. Toad. Screenshot via YouTube.

Given how ubiquitous he has become, it might be hard to fathom that the headless horseman owes his immense popularity to the work of just one man: the 19th-century American essayist and fiction author Washington Irving.

Irving didn’t conjure the headless horseman out of thin air. Similar characters had been depicted in European folklore for centuries. But it was Irving who introduced the archetype to the American mainstream when, in 1820, he published "The Legend of Sleepy Hollow," his famous short story about the ghost of a “Hessian trooper whose head was carried off by a cannonball in some nameless battle of the Revolutionary War.” Interestingly, it seems the backstory of Irving’s headless trooper wasn’t entirely his invention either. In fact, the character — whom Irving described in his story as the “commander-in-chief of all the powers of the air” — was likely based on a real Hessian mercenary who was decapitated in battle near Sleepy Hollow, New York, during the American Revolution.

Unless you’re a history buff, “Hessian mercenary” might sound as mythical as the headless horseman himself. But alas, such a creature did, in fact, exist — and apparently, they were also pretty terrifying. During the American Revolution, Britain relied heavily on German auxiliary forces — known as Hessians — to bolster its army. Renowned for their discipline and martial prowess, the Hessians were viewed by their American foes as bloodthirsty marauders who killed for money. Their escapades in the colonies were even noted in the Declaration of Independence as another example of King George’s tyrannical ruling practices.

headless horseman

Surrender of the Hessian Troops to General Washington, After the Battle of Trenton. December 1776. Wikimedia Commons photo.

Some 30,000 Hessians fought in the war, and they played pivotal roles in some major engagements, including the battles of Bennington, Long Island, and Trenton, where George Washington famously led troops across the icy Delaware river to kill Hessians on Christmas. But it wasn’t along the frozen banks of the Delaware that the man who inspired Irving’s supernatural villain lost his head; that particular Hessian was felled in the Battle of White Plains.

In 1776, Washington’s fledgling army — having recently suffered a crushing defeat in the Battle of Long Island — was in full retreat. He ordered his troops to prepare a hasty defense near White Plains, a small settlement on the northern outskirts of Manhattan. There, on the eve of Halloween, American forces engaged a combined force of British and Hessian soldiers. The gung-ho Hessians spearheaded the assault. After several hours of intense fighting, Washington’s troops broke contact and fled, leaving an estimated 50 dead American soldiers on the battlefield.

Several days later, as opposing armies continued to clash in the New York countryside, Lt. Ephraim Fenno assumed command of a lone artillery battery on top of a hill overlooking White Plains. According to the journal of American Gen. William Heath, Fenno fired a single cannonball at advancing Hessian troops, decapitating one of them, killing a horse, and effectively ending the assault.

headless horseman

The gravesite of Washington Irving in Sleepy Hollow Cemetery. Wikimedia Commons photo.

Today, a small placard marks the spot where the lone Hessian lost his head — less than 8 miles from Sleepy Hollow. While the placard was dedicated long after Irving penned "The Legend of Sleepy Hollow," and there are no explicit references to the skirmish in his story, the parallels are undeniable. Through the powers of deduction, we can reasonably conclude that the decapitation of this Hessian via cannonball — just a short distance from the town where Irving lived, died, and is now buried — served as the inspiration for the iconic character who still graces us with his presence every Halloween to sell beer and candy before resuming his eternal quest to find his missing head.

It’s been more than 200 years since "The Legend of Sleepy Hollow" became what some consider to be the first purely American ghost story. Despite all the time that has passed, an estimated 250,000 tourists still travel to the quaint village in upstate New York each year to retrace the steps of the Hessian soldier whose gruesome death inspired the tale. As for the soldier’s identity, it remains a mystery. We know neither his name nor what he looked like (except from the shoulders down).

Read Next: Before Stephen King, America’s ‘King of Horror’ Was a Civil War Vet With TBI

Mac Caltrider
Mac Caltrider

Mac Caltrider is a senior staff writer for Coffee or Die Magazine. He served in the US Marine Corps and is a former police officer. Caltrider earned his bachelor’s degree in history and now reads anything he can get his hands on. He is also the creator of Pipes & Pages, a site intended to increase readership among enlisted troops. Caltrider spends most of his time reading, writing, and waging a one-man war against premature hair loss.

More from Coffee or Die Magazine
Intel
Ukraine: Russia Hits Apartments and Dorm, Killing Civilians

“Russia is shelling the city with bestial savagery,” President Volodymyr Zelenskyy wrote in a Telegr...

March 22, 2023Associated Press
cold brew coffee soda float
Coffee
The Bitter Barista's Cold Brew Coffee Soda Float

Today, we combine the best of both worlds with this indulgent recipe, smashing together our love of coffee and ice cream with a cold brew coffee soda float!

March 21, 2023Heather Lynn
abrams tanks ukraine
Intel
US Speeds Up Abrams Tank Delivery to Ukraine War Zone

The original plan was to send Ukraine 31 of the newer M1A2 Abrams, which could have taken a year or ...

March 21, 2023Associated Press
Coffee Or Die Photo
Intel
US: War Crimes on All Sides in Ethiopia's Tigray Conflict

The Biden administration announced Monday that it has determined all sides in the brutal conflict in Ethiopia’s northern Tigray region committed war crimes and crimes against humanity.

March 20, 2023Associated Press
military pilots cancer rates
Military
Higher Cancer Rates Found in Military Pilots, Ground Crews

In its yearlong study of almost 900,000 service members who flew on or worked on military aircraft b...

March 20, 2023Associated Press
whiskey pour
Military
Veterans Lead the Way Among America’s Growing Craft Distilleries

American veterans are taking the lessons they learned in the military and changing the craft distilling industry.

March 20, 2023Mac Caltrider
military suicide veteran suicide
Military
Military Moves To Cut Suicides, But Defers Action on Guns

In a memo released Thursday, Austin called for the establishment of a suicide prevention working gro...

March 17, 2023Associated Press
us military drills japan-south korea
Intel
US, Partners Stage Military Drills Amid Japan-South Korea Talks

The Sea Dragon 23 exercises that started on Wednesday will culminate in more than 270 hours of in-fl...

March 17, 2023Associated Press
  • About Us
  • Privacy Policy
  • Careers
Contact Us
  • Request a Correction
  • Write for Us
  • General Inquiries
© 2023 Coffee or Die Magazine. All Rights Reserved