Amateur Irish sailors who gave New Zealand’s America’s Cup champions a run for their money
The Team Headcase crew after winning the Irish National J24 Championships in Sligo Yacht Club in 2021.
Pints and grand plans don’t usually mix. Ideas and ambitions forged in the fire of a night out rarely stand up to the cold light of the morning after, so there was nothing immediately exceptional about four young sailors daring to dream over a few beers at the annual ‘Cork Week’ in Crosshaven seven years ago.
Louis Molloy and Marcus Ryan are cousins from Mayo. Cillian Dickson sails out of the Lough Ree club and Sam O’Byrne got his sea legs in Howth. All four had competed on boats owned by other people. Wealthy people. Now they wanted a boat to call their own. Nothing fancy. Something accessible, affordable. Something to call their own.
Six months hadn’t passed when Ryan found himself standing in a shed behind Lidl in Kinsale agreeing to buy ‘Headcase’, a J24 keelboat. Ryan Glynn, from the Ballyholme Yacht Club in Bangor, made their quartet a quintet six months later and, with that, all the pieces were in play for one of the unlikeliest of underdog success stories in Irish sport.
Team Headcase has since won three European titles in a row. A first World title was added in Plymouth this year. Professional boats with top-class hired hands have followed in their wake.
On Wednesday, in Dun Laoghaire they lost out to Team Emirates New Zealand, winners of the America’s Cup, by the narrowest of margins for World Sailing’s Team of the Year award.
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The first solid step from loose ambition to actionable reality was a chat group and the decision to focus on the J24, the most popular keelboat in the world. Over 5,000 have been made, they cater for four-to-six people and, this was the key, it was within their price range. That’s when they spotted ‘Headcase’ online.
The name was familiar. It had won a World and three European titles in its day. Way back in the day.
“I was given the job of going down and checking it out,” says Ryan. “When I first checked it out in the boatyard in Kinsale, I probably was a bit naïve. I hadn’t spotted a lot of the problems with her before deciding to commit. Sure enough, I drove her home and realised the decks were half rotten and full of water, so we had a very big refit to do.”
That initial outlay cost them a grand total of €15,000. That, and all the costs since, are shared equally. Every cent is tracked on a spreadsheet with the rump of the outgoings swallowed up by travel and accommodation and the sails that need to be bought regularly for the bigger events.
Ryan compares those sails to tyres on a rally car in that they soon wear out and need replacing. One set could be €8,000 and might be sold on at a €2,000 loss. The cost of seven or eight people staying at venues, most of them swanky European coastal destinations, for 10-12 nights clearly isn’t cheap either. The total outlay now is up to €120,000.
So it goes, one season rolling into another like waves.
“We just don't take many holidays,” says Ryan. “Now, look, I know €120,000 sounds like a lot but that is over seven years, five lads. It works out at about €3,000 a year. I know plenty lads would spend €3000 a year on cars or drinking or whatever.”
Every man has his role. On and off the water.
Glynn, a software developer, lives in Barcelona these days. O’Byrne, who works in food delivery, is based in Malta. Dickson is in insurance and the cousins, Molloy and Ryan, live miles apart with one in Mayo where he runs a mussel farm and the other in Cork with the Irish Navy. O’Byrne and Ryan are dads now too.
Somehow, they make it all work. The foreign-based pair oversee remote stuff like planning and logistics and parts and development, and this attention to detail extends to their sailing. An international rugby coach has helped embed a process-driven performance and growth mindset. Debriefs are held after every day at sea.
Other strengths are less tangible, but provide an even stronger glue.
“It tends to work, I guess, because we're all so committed to the project,” says Ryan. “My mother has a great expression that the success of any shared project relies on balancing energy, expectation and expense. I guess we're lucky that the five of us reach a level in that.
“I'd also say there's massive satisfaction in having a shared goal and control towards it with your friends. We could be playing competitive tiddlywinks and we would probably still enjoy it just as much. It's that aspect of a shared goal with people you get on with that makes it work.”

It’s this ethos that makes them tick on the water.
Team Headcase has won Corinthian (amateur) titles but it has claimed continental and global crowns from under the noses of professional crews as well, among them strong American boats and a slick Italian navy outfit on ‘La Superbia’ who they beat off the coast of Sardinia for the second of those European successes last year.
Headcase aren’t unique. There are a handful of other amateur crews among the 50 or so boats that contest the Worlds. There’s a crew from Argentina and a couple more from Germany, but the standard model is one of a rich and capable sailor with a few of their friends and a sprinkling of top-class hired hands.
Where Headcase may be unique is in keeping the band together for so long.
“Often it loses traction in the same way that GAA teams and things like that do, where lads go to college or they go to Australia and stuff like that. Teams just fall apart. So it would be reasonably rare. There's probably three young Irish teams that fit that model, where we all kind of balance costs and share everything.
“So it's great, the whole thing is divided into Corinthian and professional classes, but it's great to be a Corinthian team and meeting these professionals as well. A lot of these will have a lot of world champions across a lot of different sailing classes on board. So yeah, it's a really satisfying part. We're passionate about it.
“And again, the consistency that you get with five guys doing that constantly over seven years, I guess does eventually yield results. It forms a team gel that the other model, when you have a wealthy owner or sponsor, is never going to get the same time working and developing together.”
The times they’ve had sound priceless.
Ryan was slagged for years over the state of the boat he bought back in 2017. One of their first road trips took them from Castlebar to Thessaloniki via Hungary and a fraught route through Serbia and North Macedonia before a highly-strung and armed customs official sent them back on a loop through Romania and Bulgaria.
In the wake of events in Dun Laoghaire, eyes are already turning to a defence of their world title next year in Sandringham near Melbourne. It won’t be cheap given the distance and logistics, maybe €75,000, so the next step looks to be a search for some form of corporate backing.
If anyone can manage it, these lads can.





