Looking Back, Giving Back: CAPERS Alum John Denny Sylliboy Reflects on His Historic Path

 Across Unama’ki (Cape Breton Island), John Denny Sylliboy is known as a trailblazer in the game of basketball. Long before coaching youth in Eskasoni and mentoring athletes at the North American Indigenous Games, John made history as the first Mi’kmaw student-athlete to play university basketball in Canada, suiting up for the Cape Breton University CAPERS from 2003 to 2007.

Today, Sylliboy works with Mi’kmaw Family and Children’s Services as a family group conference coordinator, facilitating talking circles across Nova Scotia, bringing communities, support workers and families together to build safety plans and heal. When he reflects on his journey and the path he helped forge for the generations of Indigenous ballers who followed, it all traces back to a sport he didn’t even pick up until grade 10.

A Late Start

As a kid, Sylliboy had played minor hockey, but when family finances forced him to step away from the rink, he spent several years searching for another athletic outlet. It wasn’t until he was 15 that some friends called him over to join in on a two-on-two game on the school basketball court in Eskasoni. Sylliboy had never played organized basketball, but his natural height and timing immediately stood out. Encouraged by his peers, he tried out for his high school team, quickly earning a spot due to his ability to block shots and win rebounds.

Sylliboy’s game developed rapidly, catching the attention of coaches in Unama’ki and beyond. In March of 2000, just months after picking up the sport, Sylliboy was selected as one of two Indigenous athletes from Nova Scotia to attend an elite national basketball camp in Victoria, British Columbia. It was an eye-opening week for Sylliboy, surrounded by talented Indigenous athletes from across Canada, but the moment that altered the trajectory of his life came on the final day during goodbyes when a fellow camper from British Columbia pulled Sylliboy aside.

“He hugged me and he kind of whispered in my ear that he knew I’d do something great,” Sylliboy remembers. “He said that he saw my discipline, my determination and the hard work that I put in on the court. He told me ‘Whatever you want to accomplish, I know you’ll accomplish it.’”

Motivation and Discipline

Those words echoed in his mind for the whole flight home to Cape Breton. Returning to Eskasoni, Sylliboy watched televised university basketball games and searched online records, noticing an absence of Indigenous representation on the court and resolving to become the first Mi’kmaw player at that level.

“It took a complete stranger to actually recognize and tell me something I never had the belief in myself to try for,” Sylliboy says.

He trained every night, studying Michael Jordan games and watching NCAA basketball games on television. Eskasoni’s team won a qualifying tournament and travelled to the 2002 North American Indigenous Games in Winnipeg to represent Team Nova Scotia, Sylliboy’s first chance to play against higher calibre players. 

After high school Sylliboy enrolled in the Elmitek program, a CBU pathway designed to support Indigenous students transitioning into university studies. Following his final class one day, an instinct nudged him to walk over to the home of the CAPERS basketball program, the Sullivan Fieldhouse. Peering onto the hardwood, he found a bustling gym and head coach Jim Charters, whom he had briefly crossed paths with at a community basketball clinic the year prior.

A Spot on the Team

Sylliboy says Coach Charters immediately asked him to try out for the squad.

“I was like ‘I don’t even have my stuff,’” Sylliboy remembers. “Coach said, ‘Well, I have shoes, I have a shirt and I’ve got shorts, so come on down. Just like that I went on to try out as a walk on.”

Lacing up the borrowed sneakers, Sylliboy threw himself into the drills. When the session wrapped up, Charters called for another practice the following morning at 7:00am, challenging every player to go home and figure out exactly how they could each help out the team.

For Sylliboy, answering that challenge meant returning home to Eskasoni, getting his older brother to wake him before dawn and borrowing his father’s truck for the 45-minute drive back to campus. He arrived well before sunrise, sitting quietly in the dark Sullivan Fieldhouse gym tying his sneakers before returning players arrived to flip on the overhead lights. 

When the final cuts were made, Sylliboy tracked down Coach Charters outside his office to learn his fate.

“I said, ‘I have a question, coach. Did I make the squad?’” Sylliboy said. “I’ll never forget. He looked me up and down and said, ‘Yup, you just made it in the 14th spot. You’ll be a red shirt this year, but I see what you’ve done and I like how you play.’”

Coach Jim Charters took Sylliboy’s tracksuit and shoe sizes and reminded him that practice officially started the next afternoon. Looking back, Charters remembers that walk-on decision as one of the easiest he’s ever made.

On and Off-Court Role Model

“John Denny Sylliboy’s commitment was second to none,” Charters said. “Not only did he excel in the classroom, he practiced two hours a day after school and commuted home to Eskasoni. John never missed a practice, training session or team activity. He greatly improved as a player and made his teammates better.”

That walk-on opportunity led to four years on the CAPERS roster, during which he committed to the daily grind of varsity athletics and embraced whatever role the coaching staff asked of him. Over the next four seasons, the team developed into a national contender, culminating in a 2006 run to the CIS (U SPORTS) semi-finals.

“I ended up playing on the CAPERS for four years and they were some of the best moments of my life,” Sylliboy says. “I’m so thankful for Jim Charters giving me the opportunity. I got to experience the highs, the lows and most importantly, working and growing with the team. We had ups and downs, but in the end we always came together as one.”

Legendary Teammate

Coach Charters echoed that sentiment, noting the energy John brought to the entire gym every time he stepped onto the court.

“John will go down as one of the best teammates in CAPERS history. He always worked his hardest while encouraging his fellow CAPERS in difficult times and driving them to excel,” Charters said. “Many people would travel from Eskasoni hoping to see John play. When he scored, cheers would fill the Sullivan Fieldhouse. When John entered a game at home, the whole crowd would come to life.”

After concluding his university playing career, Sylliboy turned his attention to the youth in Eskasoni, taking over coaching duties for the Eskasoni Middle School team and demanding the same commitment from his players that he had given to the game. Under his guidance, the squad progressed steadily while building a strong foundation for basketball in the community.

Continued Impact

“I started coaching them in junior high,” Sylliboy says. “We went from starting out in the B division and by the time those rookies got to grade 9 we were in the AA division.”

As those young players developed, Sylliboy encouraged them to take on higher levels of competition, whether suiting up for Division 1 high school basketball or representing Nova Scotia at the North American Indigenous Games. Today, many of those same athletes have stepped into leadership roles themselves, coaching local teams and ensuring the sport continues to thrive in Eskasoni.

“I told them, ‘You guys are the future,’” Sylliboy remembers. “I said ‘All of you need to keep passing on what I’ve taught you to the next generation of athletes.”

Whether facilitating healing circles for Mi’kmaw families or encouraging a young kid in the gym, that guiding philosophy remains at the center of everything Sylliboy does. The lessons he took from university basketball, including perseverance, showing up every day and never backing down from a challenge, continue to shape the impact he makes in his home community of Eskasoni and across the province.