Crespy Family

Every swimmer has a story—often one that begins long before their first dive into the pool. Across Swim Ontario, families live and breathe the sport: parents who once chased their own dreams now cheer from the stands, or jump back in to share a lane with the next generation. Stroke for stroke, early mornings to late meets, these families grow together in the water and beyond.

In every lane, there is history. In every family, a future.

This series celebrates the Swim Ontario families who train together, learn together, and build legacies in the sport they love. Because swimming is stronger when it’s shared—and in the stories ahead, we honour that connection.

There is quite a bit at stake during a marathon open water swim.

Don’t believe me, then try devoting almost 15 hours in the waters of Georgian Bay confronted by head winds and a wicked current while establishing a new ratified 27-kilometres swim crossing route from Tiny Township to Collingwood.

Not easy, and Derek Crespy knows it.

The 49-year-old trained diligently for almost a year and accomplished it in the summer of 2025.

As if that wasn’t a feat of grandiose proportion, Crespy was also in another test of endurance a year earlier – a 32-kilometres relay crossing from in the waters of Christian Island near the communities of Penetanguishene and Midland to Collingwood.

A former childhood competitive swimmer, Crespy prefers nothing more than a swim in a freshwater lake. In short, he thrives on swimming – even the times when he puts on a thermal wet suit and at dusk in December, with snowflakes and the ski hills in the distance illuminated, takes to the water.

Endurance swimming is challenging, stressful and exasperating at times. His type of grandiose and energetic swim requires a person using their strength, courage and perseverance. There are no rewards other than the personal accomplishments that go with the gutsy and demanding realization of achievement.

Talk with Crespy about tenacious lengthy swims - and they all take a back seat to an instantaneous event in the summer of 2024. That’s when Crespy, a freestyle swimmer, says his most important swim occurred off the shores at Sunset Point Park, which is an iconic Collingwood waterfront location.

“I enjoy training in rough water and heard a mother screaming, there was commotion about a boy drowning,” he recalled, and aware of people looking on at the time.

“Something was wrong. Waves were breaking against the rocks. A 12-year-old was drowning off shore and none of his family could swim. At the time, there was hazardous water conditions and no immediate signage. For me, it was a rescue effort. There was no time to waste, I swam out and rescued the boy bringing him back to the first responders which quickly arrived on shore.”

Crespy, who describes himself as “a regular guy around town”, would later be recognized by the Life Saving Society of Ontario with the Rescue Award of Merit. He was also invited to Port Carling in the fall of 2025 to receive the Ontario Provincial Police Commissioners Citation for Bravery.

For him, it’s a chapter in his life that will last forever.

Born in Toronto, Crespy grew up in Craigleth, about 10 kilometres west of Collingwood. It’s a picturesque part of Ontario – part of the Blue Mountains area and known more for its outdoor recreation like skiing.

Crespy is bold and audacious in many ways and has always liked adventure. After obtaining a degree in political science from Hamilton’s McMaster University, he earned more academic excellence. This time, in gemology.

For the past 18 years, his career has been in real estate. Crespy also spends his time as a volunteer parent and is a member of the Board of Directors for the Collingwood Clippers Swim Club.

As for swimming, there is always time for it. Crespy may have words of praise for Shirley Glayser, the woman who taught him to swim in lessons as a three-year old. Living near a beach helped, which led to his competitive days as a child with the then named Collingwood Y Clippers swim club and his younger days at the four-lane, 20-metres, Collingwood YMCA.

“As I got older, I’d swim recreationally,” said Crespy, married and parents to two children. “I’d watch our kids swim with the Collingwood Clippers and get inspired.

“Starting in 2023, with lane swims at the six-lane 25-metres Collingwood Centennial Aquatic Centre. Those lane swims led to the open water events. That same year, my wife suggested joining a vibrant Masters team – the Georgian Bay Squall.”

That’s a swim club of close to 100 people ranging from ages 24 to 81. In 2025, the Squall won the Swim Ontario Masters Provincial Championship for a third consecutive time.

As for Crespy, after 39 years, his first race was a 1,500-metres freestyle in Toronto. Then, an open water event in Georgian Bay.

“It was great,” he said. “Lots of fun and I proved that I still had endurance.”

When asked about what’s on his mind when he’s in open water, Crespy reflects on no distractions, no cell phones ringing but just peace and calmness. He’s contemplating his next expedition in 2026 – a bigger distance and maybe following historic sailing routes.

Along with his son, Naill, the two are regular attendees of a family favorite event which is Swim Ontario’s Open Water championships – for Age Group and Masters – and held annually at Gull Lake in Gravenhurst.

Crespy chuckled when discussing several awe-inspiring accomplishments of world-renowned endurance swimmers.

The longest assisted marathon swim reported belongs to Ross Edgley and his 510-kilometres non-stop swim down the Yukon River in 2024 which took almost 55 hours. There was also an Atlantic Ocean swim by Pablo Fernandez of 250 kilometres in the summer of 2021. We can’t leave out Sarah Thomas, who holds the record for the longest continuous swim in neutral conditions which was 167 kilometres in Lake Champlain back in 2017.

At the Crespy household, swimming is a topic always up for discussion. A family outing to the beach, not far from home, is also a regular journey in the warmer months. To benefit from 50-meters pools, lacking in the area where they reside, the Crespy’s also take year-round road trips to Guelph and the Greater Toronto Area.

“We realized that swimming was a passion for our kids, so we got them involved – the discipline, work ethic, benefits and dealing with challenges,” said Crespy. “These are very important skills that you incorporate in your life.”

Crespy’s wife swims recreationally and is pursuing her Level 2 certification as an official. She’s also the family swim logistics organizer and support leader. Niall, at 12 years of age, likes the grinding events and Lydia, who is 10 years old, thrives on the hard swim workouts.

“I like the challenge of the challenge of the sport and hopefully, one day, will swim for Canada at the Olympics,” said Niall, who at a three-day meet in Owen Sound in November of this year clocked a personal best time in the 1,500 metres and set an age club record. “I want to swim like my dad, but better.”

David Grossman is a veteran multi award-winning Journalist and Broadcaster with some of Canada’s major media, including the Toronto Star and SPORTSNET 590 THE FAN, and a Public Relations professional for 50+ years in Canadian sports and Government relations.