
Throughout June, the Cayman Compass will be publishing a series on Caymanians who first represented their beloved isles on the grandest stage of sports – ultimately paving the way for all those who came after, including the line-up heading to this year’s Paris Olympics.
The first time that the Cayman Islands flag was ever seen at the Montréal Olympic Games was in 1976, when a duo of sunburnt Caymanian sailors graced the waters of Lake Ontario in Canada.
Gerry Kirkconnell and Carson Ebanks became the first to officially compete for the nation at the mega event, in what was an experiment of sorts.
“They were just looking for someone to send because once you sent somebody, the committee got access to funds and things that they didn’t have prior to getting accepted; so part of my job was to be the guinea pig to go there,” Kirkconnell told the Compass.
Kirkconnell, now 66, was born a year before Cayman had its own official flag. His father, the late Captain Eldon Kirkconnell, ran ships to Jamaica while his son fished on the cliffs in Cayman Brac.
Although it seemed like Gerry Kirkconnell’s future was to be a boatman, instead he found himself loving the sport of football, like many in those days.
“I really loved football; I played in the defence but I damaged my knees at a fairly young age and that limited the sports that I could do because I even went back and got re-injured which resulted in surgery,” Kirkconnell said, noting that he played for the Triple C School team and a club from West Bay.
With banged-up knees, only watching from the sidelines, Kirkconnell discovered a new passion after a friend of his brought him back to his roots.
“A friend of mine, his father bought him a small sailboat and I learned to sail and started sailing in that little boat,” he said. “I managed to talk my dad into getting me one and then I got into racing off Seven Mile Beach.”
From there he joined the Sea Scouts, which catered to competitive sailing, rowing and swimming in the late ’60s, early ’70s.
“Tim Adam actually sailed with me in the beginning; it was a single-man boat, but we were so small, we both fit in it and then after that, I just started to race on my own and I fell in love with it.”
Around the age of 14, Kirkconnell, with several other sailors under the Sea Scouts, travelled to Grenada to compete in a regatta.
“That was probably my first race outside of Cayman,” he said. “It was a group of us, John Bodden, Donald McLean, William Nixon…and that is where I got to know Carson [Ebanks].”
Montréal Games
That was the start of a historic pairing of two Caymanian youngsters, who eventually got selected without qualification to represent their country in the 470 event at the Olympics in 1976 – Peter Milburn also attended those games for Cayman, but as an alternate.
At the time of the event, Kirkconnell, 18, and Ebanks, 20, were like deer in the headlights and although they recognised that winning a medal was only something they could dream about, they held their own as first-timers on the big stage against 40 nations sending their very best.
“We had no idea what we were doing,” Kirkconnell said. “We had no coach or anything to help us, so we were just thrown into the deep end and I think we held our own.”
He said his original training and competing along Seven Mile Beach didn’t prepare them enough for one of the five Great Lakes of North America.
“It was a big lake and when the wind started, it got rough and on top of that, we were sailing in really cold water which we weren’t used to. It was a big change,” Kirkconnell recalled, noting how inexperienced they were compared to the rest of the fleet.
However, the sport was and remains expensive, he added, pointing out that to become successful, they would need to constantly travel to regattas with their own boats.
“That takes a lot financially to be able to do that, and for us, that was impossible. We would get to one or two regattas but we were not getting to go consistently.”

But despite their inexperience, lack of a coach and competing in cold water, Kirkconnell and Ebanks still managed to hold their own. In fact, in one of their six races, they temporarily held fifth position, ahead of dozens, but ultimately finished 18th.
“We actually didn’t perform that bad but two races hurt us really bad for the overall result,” Kirkconnell said.
“There’s a was black flag rule – if you were over the line five minutes before the race, you were disqualified; we didn’t know about that rule and we went over the line in that period and we couldn’t even restart,” he explained, noting that they were deemed last for that race.
“We had another complication in the last race. We were trying to overtake some of the boats in front of us, but we left the spinnaker up for too long and, coming off of a wave, I can’t remember if Carson slipped but we were going really fast and the boom hit the water and … it ended up causing us to capsize.
“It was blowing, it was rough, so by the time we got the boat back up, everyone had passed us. The spinnaker was all tangled up, so we ended up not finishing that race.”
But, even so, the Montréal Games were an unforgettable experience for the pair, though that would be the last Olympics for Kirkconnell.
While he did qualify for 1980 Moscow Olympics, he was unable to attend due to events beyond his control.
“[The Games were] boycotted, so nobody went,” he said. “We were much better prepared for that from what we learned in the 1970s. Sports brings people together and politics always seem to divide people.”
When asked what it meant to be one of the two people to represent the Cayman Islands at their homeland’s Olympic debut, Kirkconnell said, “I am longing to see Cayman win a medal and we might do it this year. That would please me the most, to see what we started back then and someone finally gets us to the top.
“I am really hoping that I will see that someday because that is what we started, not necessarily for us, but for all the Caymanians that came after.”
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I well remember sailing with Gerry and Ken Hall in the annual regattas that were held off West bay Beach in the early seventies, initially using Sunfish, and then Lasers. They were the two to beat and I had some great battles, winning the Cup one year in the last of the six races on the last leg, tacking to the finish line.