At 104, Montserrat’s John ‘Cannon’ Fenton is still sharp and sharing stories about his intriguing life

by Edwin Martin

“I’m not really a religious man but I’m not one of the bad ones,” says John “Cannon” Fenton, who turned 104 in March.

It is 5:30 p.m. on a balmy Tuesday in July. Dusk beckons over Salem, a village whose name literally means “peaceful and complete.” John Fenton is seated on a sturdy gray plastic chair on his verandah. He is facing the Salem Park Road, one of the main arteries in the ever-flowing village in central Montserrat. As each vehicle passes, the drivers honk their horns or yell out the name by which Fenton is best known.

“Cannon! How you doing?” shouts Salem native Julian Romeo, who slows his Jeep to exchange pleasantries. Seconds later, a stentorian voice emanates from across the street. “John Cannon!” bellows Danny Sweeney, another area resident.

Each greeting is laced with unmistakable reverence for Fenton, Montserrat’s second-oldest resident at 104. While most of his contemporaries are infirm or interred, Fenton lives alone and still cooks his own meals. He enjoys a cold beer each evening. Heineken and Amstel are the most popular brands on Montserrat but Fenton prefers Carib Lager.

Fenton enjoys recounting stories, of which he has countless. He rattles off anecdotes about growing up in St. John’s Village, becoming a successful businessman at 15 after dropping out of school, his eventful two decades in England and subsequent return to Montserrat.

A father of nine and grandfather of 13, Fenton remains a legend in St. John’s, where the locals once urged him to enter politics (he politely declined). These days he has ample time to relax and reflect on a journey that is truly one for the ages.


“I was born on the 12th of March, 1918,” says Fenton, who hails from Dick Hill, St. John’s, in the north. He is the only child of his mother, who died when Fenton was 4 years old. His father later remarried and sired “seven or eight” children, Fenton says.

Fenton attended St. John’s School, which was an appendage of the Anglican church. He dropped out in Standard 3. “They refused to pass me to Standard 4 so I got fed up and left,” says Fenton, who at age 14 became known as “Cannon” – an alias he gave himself. “I gave all my friends their nicknames too,” he says with a tinge of pride.

Unlike some dropouts, Fenton was no delinquent or loafer. He was willing to work.

“I wasn’t a scholar but I survived. Where the airport is right now [in Gerald’s], back then you could go down there and Task,” he says, a term for working as a laborer.

Photo credit: eBay
Sea Island cotton was once such as staple on Montserrat that it was featured on this stamp from the early 1950s.

During the 1930s, cotton was king in Montserrat. The pear-shaped island produced Sea Island cotton, which was in high demand because its long fibers yielded luxurious fabric that was silky and soft. St. John’s flourished with cotton, and Fenton says he once managed about eight acres. He hired workers and teamed with legendary Plymouth businessman M.S. Osborne, who shipped the cotton to England. Still a teenager, Fenton invested his earnings wisely and purchased a property on Challenger Road in St. John’s.

“I bought a shop for 9 pounds and the land for 3 pounds,” he says. “I was the first person to live on Challenger Road. Back then it was called Cart Range. That was around 1933.”  

Challenger Road, a glorified alley that runs north-south, serves as an avenue for two main roads in St. John’s. The northern end is near the current site of Glendon Hospital. Fenton explained how the road got its name.

“At one time the road was just wide enough for a cart,” he says. “Then they widened it. There was a bus called Challenger [owned by the Howe family]. It was the first bus to drive through there. That’s why they call it Challenger Road.”

Challenger Road remains quite narrow. Due to lax enforcement of zoning laws, homes were built on either side of the road, making it virtually impossible to widen the strip without infringing on property. However, it is still a two-way street, making for awkward maneuvering when vehicles heading in opposite directions cross paths.

Fenton says he once owned three shops in the area – two in St. John’s and one in Davy Hill. He sold food, liquor, cigarettes . . . “Everything!” he says with a smile.A look at Challenger Road in St. John’s, where “Cannon” Fenton once lived and owned a shop.


In 1941, Fenton married Sarah “Bertie” Ryan of nearby Drummonds. They had seven children: five boys, two girls. In 1943, eldest son Joseph sadly died at age 4. “One day I heard him snoring . . . but he wasn’t sleeping,” Fenton says. “We took him to the doctor and then the hospital. When they told me my son was going to die, I fainted.”

In 1954, Fenton was still enjoying business success but saw many of his friends leaving for England during the Windrush era that followed World War II. Fenton became intrigued about the Mother Country.

“I used to lend people money when they were going to England,” he says. “I thought that in England you could just go up there and walk on money.”

Fenton closed his shops and sailed off to Britain. But when he arrived he was taken aback. “It was cold . . . and foggy. For days you didn’t even see the sun.” Fenton wanted to return to Montserrat right away but knew he would look somewhat foolish after closing his shops.

In 1956, Fenton sent for his wife. During the weeks-long voyage to England, the ships often made stops in other European ports. When they docked in Italy, Bertie Fenton was not wearing the proper attire for the frigid weather and developed a serious illness. She died shortly after arriving in England and was interred in the UK.

With his children now motherless and grieving in Montserrat, Fenton returned home. He purchased a bus. “Marse Gen [M.S. Osborne] ordered it for me,” he says. One day in 1958, he was transporting passengers when the bus got a flat tire at the top of Fogarthy Hill in St. Peter’s near the famous “S” corner. Fenton tried to change the tire, but the spare was also flat, and he didn’t have a pump. The passengers got on another bus and Fenton got a ride from a friend. When he returned to fix the tire, vandals had burned down the bus.

“Bad mind,” he simply says when asked the motive. “I had that bus for less than a year.”

Distressed by the incident, Fenton returned to England and eventually sent for all his children. He later remarried and also adopted a new profession in the UK: house painter. He remained in England until 1974, when he decided to give America a try. He moved to New York, but, now in his 50s, he could not find consistent work. He bought his current home in Salem and came home in 1978.

His most lucrative days as a house painter came in the subsequent years. He teamed with contractor Noel “Fenty” Fenton (a distant relative) and got steady painting jobs. “I would sometimes paint a whole house by myself,” he says. “I remember one job I got $10,000.”

In 1994, “Cannon” stopped painting on the advice of his doctor. The years of inhaling toxic paint fumes had taken a toll. “They said it was affecting my lungs.”

That didn’t curtail his work ethic. He worked in the fields, harvesting crops, notably cassava. He was omnipresent, spending time between Salem and St. John’s.

In 2018, he celebrated his 100th birthday with a lavish bash at Tropical Mansion Suites Hotel. “We had 100 guests, white and black. That party cost $15,000 . . . and breeze.”

A program from John “Cannon” Fenton’s 100th birthday celebration in 2018.


With any long existence, adversity is always hovering. Losing his young son and his wife still stings more than six decades later. But Fenton says overall he has had a happy life. He’s still lucid and active and could pass for a man in his 70s. He’s grizzled but not gaunt. He drove vehicles until he turned 100, then stopped at his own discretion. He endures chronic pain and has lost some feeling in his left arm, yet he still heads to his garden on his good days and harvests his trademark cassava. He says he didn’t expect to reach a century. However, there was family precedent.

“My aunt Hannah Fenton lived to be 108,” he says, before quickly adding, “I don’t think I’m going to reach there. Not with all these pains I have.”

Nonetheless, Fenton continues to stick to his winning formula: “I have my soup every day and a beer in the evening.” He is constantly surrounded by family and friends who keep his mind and intellect engaged. As of early August 2022, the only person in Montserrat older than Fenton was 105-year-old Sarah Piper, a native of Frith’s Village who was residing in the Golden Years Home For The Elderly.

It is now 6:30 p.m. Dusk has officially taken center stage but Fenton is still holding court. Some of his tales are humorous, such as the days when men would migrate to England and then send for their wives – and their “side chicks” as well. One story segues into another as Fenton exhibits the memory of a man half his age. His life story is not just his own. It’s also the story of a people, straddling several generations of Montserrat’s colonial, cultural and complicated history.

It’s almost time for Fenton’s evening beer but another story is always brewing from the centenarian.

They never get old. 

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