History has a funny way of smoothing out the rough edges of people until they look like statues instead of humans. When people talk about the Prince of Donegal, they’re almost always referring to Red Hugh O’Donnell (Aodh Ruadh Ó Domhnaill). He wasn’t just some guy in a crown. Honestly, he was a rebel, a fugitive, and eventually, the last great hope for a Gaelic Ireland that was rapidly disappearing under the weight of Tudor conquest.
He was a firebrand.
Born around 1572, Hugh didn't have a quiet childhood. The English government was so terrified of the potential alliance between the O'Donnells and the O'Neills that they kidnapped him when he was just fifteen. They lured him onto a merchant ship at Rathmullan by promising him wine. Instead of a drink, he got chains and a cell in Dublin Castle.
He stayed there for over four years. Can you imagine that? Spending your teenage years in a dark, damp prison because of your last name.
The Great Escape from Dublin Castle
Most people know about his second escape attempt because it’s basically the stuff of movies. It was the dead of winter in 1592. Hugh and two of the O'Neill brothers, Henry and Art, slipped down a silk rope into the sewers of Dublin. They trekked across the Wicklow Mountains in a literal blizzard.
They weren't wearing coats.
By the time they reached the safety of the O'Byrne clan, Art O'Neill had died of exposure. Hugh survived, but he lost both of his big toes to frostbite. He returned to Donegal a crippled but furious young man. He was twenty years old. His father, the reigning King of Tyrconnell, stepped aside, and Hugh was inaugurated as the Prince of Donegal at the Rock of Doon.
If you go to the Rock of Doon today, near Termon, it’s remarkably quiet. It’s just a limestone outcropping in a field. But standing there, you realize this was the "Westminster Abbey" of the north. It’s where the O’Donnell chieftains were made.
The coronation wasn't about a fancy throne. It was about standing on a stone that supposedly held the footprint of the first chief and swearing to protect the land.
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Why the O’Donnell Dynasty Matters
The O’Donnells weren't just local lords; they were international players. They had links to the Spanish court and the Vatican. Donegal—or Dún na nGall (Fort of the Foreigners)—was their stronghold. From the Castle in Donegal Town, they controlled the fishing rights, the trade routes, and the loyalty of dozens of smaller clans.
The castle is still there. Well, a version of it is.
Sir Basil Brooke rebuilt much of it in the 1600s, adding the Jacobean windows and the massive fireplace, but the lower levels are still the original O'Donnell stonework. You can feel the coldness of the stone and see how thick the walls are. They had to be. Life in 16th-century Donegal was a constant state of "watch your back."
The Nine Years' War and the Spanish Connection
Hugh didn't just sit in his castle. He spent the next decade fighting the Nine Years' War against Queen Elizabeth I. He was a master of guerrilla warfare. He used the Donegal bogs and the mountains of the Bluestacks to his advantage, ambushing English columns and disappearing before they could regroup.
But he knew he couldn't win alone.
He needed Spain.
This is where the story gets tragic. In 1601, the Spanish finally sent a fleet, but they landed in Kinsale. That's the opposite end of Ireland. Hugh had to march his entire army from the north to the south in the middle of winter. It remains one of the fastest forced marches in military history.
They lost.
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The Battle of Kinsale was a disaster. The coordination between the Irish and the Spanish fell apart. Hugh, ever the optimist or perhaps just desperate, sailed to Spain to ask King Philip III for another army. He never came back.
The Mystery of Simancas
Hugh died in Simancas, Spain, in 1602. He was only 29 or 30. For centuries, people thought he was poisoned by an English double agent named James Blake. Modern historians are a bit more skeptical, suggesting he might have died from an infection related to a tapeworm, which was pretty common back then.
In 2020, archaeologists in Valladolid actually found what they believe is the site of his burial in the Chapel of Wonders. They found bones. They found a coffin.
They didn't find the big toes.
Since Hugh lost his toes to frostbite after his escape from Dublin Castle, the absence of those specific bones would be a huge clue. But the site had been built over for centuries, and the excavation was incredibly difficult. Even if they never definitively prove those specific bones are his, the search reignited a global interest in the Prince of Donegal.
Visiting the Lands of the Prince
If you’re traveling to Donegal to find the ghost of Red Hugh, don't just stay in the town. You have to move.
- Donegal Castle: Start here. It’s the heart of the O'Donnell power. The guided tours are actually decent and explain the transition from Gaelic fortress to English manor.
- The Rock of Doon: Located near Kilmacrennan. It’s on private land, but there’s a path. It’s atmospheric and overlooked by most tourists.
- Magherabeg Abbey: The ruins of the Franciscan Friary where the O'Donnells were patrons. It’s a somber place, right on the water.
- The Flight of the Earls Centre: Head to Rathmullan. This is where the Gaelic order officially ended in 1607, a few years after Hugh's death, when the remaining chiefs fled to Europe.
People in Donegal still talk about the O'Donnells like they were here last week. There’s a pride in that lineage. It’s not just about a title; it’s about a specific brand of northern defiance.
Common Misconceptions
You’ll see a lot of gift shops selling "Prince of Donegal" trinkets. Here’s the reality: Hugh wouldn't have called himself a prince in the way we think of Prince William. He was a Taoiseach (Chief) or a Rí (King) of his territory. The "Prince" title was often a Latinized version used in correspondence with European royalty to make the Irish hierarchy understandable to the Spanish and French.
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Also, he wasn't always a hero to everyone. He was a warlord. He burned crops. He took hostages. He was doing what was necessary to survive in a brutal century, but he wasn't a saint. He was a politician with a sword.
The O'Donnell crest features a cross held by an arm in armor. Legend says it goes back to St. Patrick, who supposedly marked the shield of an O'Donnell ancestor with his staff. Whether you believe the myths or not, the iconography stuck.
Practical Steps for History Buffs
If you're planning to dig deeper into the life of the Prince of Donegal, start by looking at the Annals of the Four Masters. It’s one of the most important historical documents in Irish history, and it was written by monks in Donegal under the protection of the O'Donnells.
You can see a statue of Red Hugh in Donegal Town, right near the pier. It looks out toward the bay. It’s a good spot to start a walking tour.
- Check the opening times for Donegal Castle, as they change seasonally. It’s usually open daily from 10:00 to 18:00 in the summer.
- Rent a car. You cannot see the Rock of Doon or the remote ruins via public transport. The roads are narrow. Be prepared to reverse for a tractor.
- Read "The Life of Hugh Roe O'Donnell" by Lughaidh Ó Cléirigh. It’s a contemporary biography written shortly after his death. It’s biased as heck, but it’s the primary source for his life.
- Visit Valladolid if you're ever in Spain. The city has embraced its connection to the Irish prince, and there’s a plaque marking where he died.
The story of the Prince of Donegal is ultimately a story of "what if." What if he hadn't died in Spain? What if the Spanish had landed in Derry instead of Kinsale? Ireland might look very different today. But even without the "what ifs," the sheer grit of a man who escaped a high-security prison and marched across a country on frostbitten feet is enough to keep the legend alive.
The O’Donnells may no longer rule from the castle, but their name is on every second shopfront in the county. In Donegal, history isn't behind you; it’s right under your feet.
To explore the O'Donnell legacy further, visit the Donegal County Archives in Lifford. They hold various land records and maps that show exactly how the O'Donnell territories were carved up during the Plantation of Ulster. Understanding the map is the best way to understand the man.