Published: May 11, 2026 · Slapshot Diaries Editorial
Chris Simon was one of the rare enforcers who could play — really play. He won a Stanley Cup with the 1996 Colorado Avalanche as a rotation winger who chipped in 16 goals during the regular season. He was an Ojibwe man from Wawa, Ontario, who carried his First Nations heritage with quiet pride through fifteen NHL seasons. And he was the player who, on March 8, 2007, swung his stick into the face of Ryan Hollweg and received the longest suspension in modern NHL history.
Chris Simon was born on January 30, 1972, in Wawa, a small town on Lake Superior in northern Ontario. He was the second of nine children in an Ojibwe family that valued community, work ethic and resilience.
Simon's path to the NHL wasn't smooth. He was drafted 25th overall by the Philadelphia Flyers in 1990, then traded to Quebec as part of the Eric Lindros mega-deal in 1992. He moved with the Nordiques to Colorado in 1995 and was a depth winger when the Avalanche won the 1996 Stanley Cup — his only championship.
Simon was bigger than most fighters at 6'3" and 230+ pounds. Unlike many enforcers who played four-minute shifts and disappeared the rest of the game, Simon was trusted with regular ice time. He scored 29 goals in 1999-2000 with the Washington Capitals — a season that would have made him a useful winger even without his fighting role.
But the fights came too. Simon fought roughly 89 times across his career according to HockeyFights records, taking on the heaviest hitters of the era. He didn't seek fights, but when called on, he answered.
It was a routine Madison Square Garden game between the New York Islanders and Rangers. Late in the third period, Rangers forward Ryan Hollweg hit Simon along the boards. Simon got up, turned, and brought his stick up into Hollweg's face two-handed — chopping motion, blood on the ice, ejection.
The NHL came down hard. Commissioner Gary Bettman handed Simon a 25-game suspension, the longest in modern NHL history for an on-ice incident. Hollweg recovered. Simon never quite did. The incident overshadowed his entire career in subsequent media coverage and became a reference point in concussion-era discussions about hockey violence.
Simon was outspoken about his Ojibwe heritage in an era when First Nations representation in the NHL was rare. He visited reserves and youth hockey programs, often signing autographs for hours and reminding kids that an NHL career was possible.
His teammates remembered him as soft-spoken off the ice — almost shy. Coach Marc Crawford in Colorado said Simon had "two completely different personalities — quiet, gentle, almost vulnerable off the ice, and a wrecking ball on it."
Simon retired in 2008 after a season in the KHL. Like many enforcers of his generation, he showed signs of post-career cognitive decline. His family later spoke about anger, sleep problems, and isolation in his final years.
On March 18, 2024, Chris Simon died by suicide. He was 52. His family announced afterward that they believed CTE — chronic traumatic encephalopathy — had contributed to his decline, and pledged to donate his brain to the Concussion Legacy Foundation for study. The announcement made Simon part of the growing list of enforcers whose post-career struggles have reshaped how the sport thinks about head injuries.
Chris Simon's career resists easy summary. He was a Stanley Cup winner. He was a Pos-2 ranked enforcer in his prime. He was the man who swung a stick at another player's face. He was a quiet Ojibwe family man who battled demons most of his teammates never saw.
If you came of age watching 1990s and 2000s hockey, Chris Simon was a constant — somewhere on the periphery, big number on the back, ready to drop the gloves but also capable of putting one in the net. His passing in 2024 closed a chapter that the NHL is still struggling to write.