Kaleem Simon living the World Cup dream in the Emerald Isle of the Caribbean

It’s a remarkable tale which began when the 24 year-old was contacted by the Montserrat Football Association on Instagram as part of a unique social media scouting mission.

Four weeks ago Kaleem would never have envisaged he would be reconnecting with his roots and representing the homeland of his father.

The football career of the former Longford Town and Bohemians midfielder, whose mum Karen Strawbridge hails from Derry, was at a standstill in London where his team Welling United’s league campaign was halted due to Covid-19.

Qualifying through his late paternal grandmother, Mary Philip, Kaleem went from playing in the English National League to playing international football on the world stage on Wednesday - a ‘once in a lifetime’ opportunity.

The Dubliner had always dreamed of donning the green shirt of his national team but never did he think the green would be that of Montserrat.

Known as the Emerald Isle of the Caribbean Montserrat is a nation of just 5,000 inhabitants. It has been rebuilding its national football team and has cast its net far and wide in an effort to find eligible footballers plying their trade around the globe.

Things quickly fell into place for Kaleem who received a shock call-up when a member of the recruitment team sent him a message on his Instagram account.

Kaleem takes up the story. . . “Basically the Montserrat F.A. followed me on Instagram. I think I have it on my profile: ‘half Irish, half Caribbean’ but nothing to do with Montserrat and there’s plenty of islands in the Caribbean.

“I got a message to say it was someone from recruitment and they asked if I would be interested in representing them.

“I didn’t know much about Montserrat so never thought before of putting my name forward. But when I saw this I was over the moon.

“I sent some of my League of Ireland footage and within a couple of weeks the manager texted me and said he was building a younger squad with new players and asked if it would be something I would be interested in.”

After just one training session with the squad in Stanford, Kaleem jetted off to Curaçao where Montserrat began their long journey on the road to Qatar 2022 against Antigua and Barbuda at the Stadion Ergilio Hato.

He came off the bench to play at left-back for the final half hour of the 2-2 draw against their fellow islanders as the first round of CONCACAF World Cup qualifying got underway. And he hopes he made his granny proud.

“We were disappointed not to win as we were the stronger team,” he said. “On a personal note, I actually got on for 30 minutes as a left back and played my heart out. And I feel I made my granny proud winning tackles and driving forward.”

That journey continues on Sunday with the visit of Group A favourites El Salvador and he’s hoping he earns his second international cap.

Kaleem is proud of his Montserrat roots and grateful to have the opportunity to represent his family and particularly his late granny who passed away last January.

“First of all, I’m so grateful for the opportunity,” said Kaleem from Montserrat’s idyllic base in Curaçao.

“There are so many top class players playing in the Premier League, La Liga, Bundesliga, Serie A, who are just unbelievable talents who work hard but don’t get the opportunity to represent their country, so it’s massive.

“I will always be grateful to Montserrat. Not everyone will get this chance and it’s a once in a lifetime opportunity.”

When he pulled on the green shirt, his granny was foremost in his thoughts.

“I’m just grateful for such a good experience. In my mind I’m thinking, I want to do it for my family. I want to do it for my late granny who passed away in January from Covid. She had a chest infection and tested positive in hospital and died peacefully there.

“That’s my granny who is from Montserrat. I want to do this for her and for my family, for my dad,” he added.

“When I used to say I would love to put on a green shirt, I’d have been thinking of Ireland but now it’s the Montserrat shirt.

“My granny would be over the moon and so delighted. That’s what’s carrying me, to do it for her and then for my family at home.”

Montserrat’s connection with Ireland is fascinating. It’s the only country outside Ireland where St Patrick’s Day is celebrated as a public holiday!

The island’s Irish heritage dates back to the 17th century when it became a haven for Irish catholics - originally sent into exile by Oliver Cromwell - who had been persecuted on other Caribbean islands.

Indeed, the Irish had such a strong influence on the island’s developing culture that there remains a rich mix of Irish and African heritage with Irish surnames such as O’Connor, Fitzgerald, Murphy and O’Carroll still found in Montserrat today.

More recently thousands of Montserratians relocated to the UK during the 1950s, including Kaleem’s granny, who later returned before permanently migrating to London in 1989. Others were displaced by the Soufrière Hills volcano’s catastrophic eruption in the ‘90s and began their new lives in London.

It was in the English capital where Kaleem’s dad, Omar Simon - whose father was from Dominica Republic - met his mother who had left her family home in Benvarden Avenue in the Waterside in pursuit of work.

Having grown up in south Dublin, Kaleem would make regular trips to Derry with his two brothers to spend time with his granny Sheila, now living in Knockwellan Park, and his uncle Paul Strawbridge, a member of Foyle Paddlers.

Kaleem is proud of both his Irish and Caribbean roots and he’s delighted to finally get his first taste of island life this week.

“I haven’t posted anything on Instagram just yet but once I do I think people will get quite jealous,” he beamed. “It’s about 27 degrees and the sea is just clear, light blue and there’s palm trees everywhere.

“I’m on a private beach and there’s a little pier you can jump off. There’s a swimming pool and a gym. It’s beautiful.”

Kaleem admits to being ‘ignorant’ to the extent of the ‘phenomenal’ Irish connection with the island and wants to learn more about the history of Montserrat.

“It’s amazing. It’s halfway across the world so it’s phenomenal there’s that connection.

“My dad was born in London,” he explained. “My granny came from Montserrat and went to live in London. When my dad was two my granny sent him back to Montserrat with his granny, basically to look after him while she was working and while my grandad was working in London.

“He stayed in Montserrat until he was about 14 and then came back to London. There were stories about him jumping off cranes and into the sea and climbing to the top of trees to pick coconuts. It was just a different lifestyle.

“He never went back until two or three years ago when my dad wanted to bring my granny back to see everyone she hadn’t seen for so long. It was the first time in about 27 years.”

It proved to be her final homecoming as she sadly passed away this year, making this experience even more special for Kaleem and his family.

“I’ve never been to Montserrat so haven’t got to witness their culture or anything like that. With Covid the island is more or less closed and we’re playing our games in Curaçao.

“As I play more and more, I’ll get to know more about the history. One of the lads on the team told me his granny was from Belfast. Most of the players are based in England but you would never think any of them would have family from Ireland but the link between Ireland and Montserrat is quite strong.”

The ex-Bohs man, who was approached by former Derry City coach Kenny Shiels about a potential move to Brandywell in 2016, hopes being involved in international football will prove a springboard for his career.

“Big time! I was saying that to my mam. She wouldn’t know too much about football so to explain to her what this means I told her that out of hundreds of thousands of teams out there all over the world, there are 200 odd countries with 25 players max in their squad.

“You’re talking about maybe a couple of thousand players representing their countries from millions of footballers who have tried to make it at international level and play at the highest stage of football.

“If we could progress, and hopefully we can, to the World Cup, but even the qualifiers are such a platform to do your stuff and see what happens from there. There might be different avenues that open up, avenues you might have never known about.”

Overseeing Montserrat’s resurgence is ex-Man City player and former Scotland international Willie Donachie.

Montserrat are ranked 183rd in the FIFA rankings - a far cry from 2002 when they lost 4-0 to Bhutan in the ‘other World Cup final’ between the globe’s two lowest-ranked teams at the time.

Former Newcastle and Spurs striker Ruel Fox is the nation’s most notable former player. He also spent a period as the team’s head coach before taking up a scouting role to step up Montserrat’s talent detection programme in England.

Kaleem explains the little Caribbean island has high hopes of qualifying from the complicated CONCACAF World Cup qualifiers- a UEFA-style Nations League.

Should they top Group A, which includes Grenada, US Virgin Islands as well as Antigua and El Salvador, Montserrat must then go through two more rounds of qualifying before reaching the Finals in Qatar.

“It’s the World Cup qualifiers and even if we get knocked out at this stage it’s still the World Cup qualifiers,” he stressed proudly. “But we have ambition and want to see how far we can go.

“Anyone in the world would love to play in the World Cup, whether a pro or an amateur, it would be a dream come true.”

The permutations are complex but given Kaleem’s incredible story, it is not that far-fetched for a young lad who began his football career in the League of Ireland. Finishing the job would crown a tale worthy of a film script.