Life Imitating Art: Frank McNally on the Art O’Neill challenge, recreating an actual 1592 jailbreak

Confusingly for some of us, the pursuers had set off earlier on Friday night, before the escapees

The start of the annual Art O'Neill 2026 challenge at Dublin Castle.
The start of the annual Art O'Neill 2026 challenge at Dublin Castle.

Being near Dublin Castle on Friday at 11pm, I stopped by the City Hall gate to catch the start of the annual Art O’Neill Challenge.

This commemorates a real-life event of 1592, when Red Hugh O’Donnell and the brothers Art and Henry O’Neill escaped from a castle tower – cutting their chains and dropping down through a toilet chute into the cesspool (aka the River Poddle), before fleeing across the mountains.

This year’s re-enactment was a bit late, strictly speaking. Like another now-annual commemoration of events involving snow and fatality – James Joyce’s The Dead - the original escape happened on January 6th.

But whereas enthusiasts for the former celebrate it by having dinner indoors, the masochists who relive the jailbreak do so by running or walking 62km overnight, much of it on mountain trails.

On the plus side, they skip the toilet part. And in fact, they can choose from two events, one less extreme.

In the original escape, guards chased the prisoners as far as the mountains, then gave up. So if they don’t fancy the Challenge, commemorators can instead do the Art O’Neill Pursuit: a mere 25km. Confusingly for some of us, the pursuers had set off earlier on Friday night, before the escapees.

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The weather was benign for the latest re-enactment. That, proper clothing and the close attentions of the Dublin & Wicklow Mountain Rescue ensured that nobody died en route. Unlike poor Art O’Neill, whose burial site the challenge participants passed during the night.

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In his biography of Hugh O’Neill, Sean O’Faolain describes the original escape. O’Neill, aka “Tyrone”, was no relation to the O’Neill brothers, but a powerful and wily figure in Gaelic Ulster, whose bribery probably helped make the event happen.

He arranged for the prisoners to be met below the tower by one of the O’Hagans, his close allies, with whom they then slipped out into the streets. Henry O’Neill went his own way, while the others struck for Blessington, and there began the climb to Glenmalure, the deep Wicklow valley held by Tyrone’s friend, Fiach MacHugh O’Byrne:

“From Dublin to Glenmalure, even today, over good roads, is a very heavy march… Then, in deep winter, with the snow falling heavily, over rough by-roads and slight goat-tracks… it was a superhuman test, and Art O’Neill could not make it.

“He had grown fat in jail, had hurt his leg in dropping down from the privy, and was soon being dragged along by Red Hugh and O’Hagan. After a night and a day of this agony, they finally managed to reach a col now called Table Mountain…

“The final stage would be down an impassable declivity into the glen where only sheep had gone before. Red Hugh and O’Neill could struggle no farther. They lay down in the snow to sleep, and O’Hagan forced himself forward to bring help.

“When Fiach MacHugh O’Byrne’s men arrived, they found the two bodies with shrouds of freezing hail edged about them, their scanty clothes frozen to the skin, and every limb apparently lifeless.”

O’Neill was indeed dead. Red Hugh’s extraordinary constitution just about saved him: “With Tyrone’s assistance, he was smuggled stage by stage to the North, where he was under the care of his father’s doctors till April. He had to have his two big toes amputated.”

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The digitally reduced Red Hugh, only 20, thereby enhanced his reputation as a hero. His father promptly abdicated the clan chieftainship in his favour. But the other surviving escapee was less lucky.

The O’Neill brothers were rivals to “Tyrone”, who may have wanted them out of jail mainly to prevent the English using them. O’Faolain speculates he would not have been unduly upset by Art’s fate. As for Henry, when he arrived home, Hugh O’Neill had him jailed again locally, to be on the safe side.

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Before going to bed on Friday, I posted a video of the event on various social media sites and woke Saturday to discover it had gone viral. Even on Bluesky, the clip garnered 200 likes and retweets. On Instagram, it has since had 130,000 views. As for Twitter/X, the figure is 415,000.

Reaction was overwhelmingly positive, ranging from those amazed that such an event exists to a tweeter who responded: “Words cannot express how much I love Ireland and its people.”

On the other hand, going virial on Twitter/X is a bit like escaping a medieval castle through the toilet chute: there’s always a cesspool waiting at the bottom of the comments.

In this case, various bots, cranks, and Trump admirers somehow shoe-horned in their agendas, including: “Woke slop”, “What pronouns did Red Hugh O’Donnell use?” and “They almost all appear to be men – sex differences are real.”

That last poster should have looked closer. There were 40 women among the (200 maximum) entries for the Challenge. The first home of those was Kristen O’Sullivan, whose time of 8 hours, 7 minutes and 7 seconds would have made her 6th overall. The winner of the men’s race was Andrew Tees in 06.13.14.