As told to: Staff Writer
But the Grimson story doesn't end with dropped gloves and bloodied knuckles. Unlike many enforcers whose lives spiraled after hockey, Grimson reinvented himself completely. He earned a law degree, became a player agent, and emerged as one of the most articulate voices advocating for player safety and mental health awareness. His journey from hired fist to hired attorney is one of hockey's most remarkable transformations.
Stuart Grimson was born on May 20, 1965, in Kamloops, British Columbia - a hockey hotbed nestled in the interior of Canada's westernmost province. Unlike many enforcers who came from rough backgrounds, Grimson grew up in a stable, supportive family that valued education and faith.
"My parents always stressed education," Grimson recalled in interviews. "Hockey was wonderful, but they made sure I understood it wasn't forever. That perspective probably saved my life later on."
Grimson's size became apparent early. By his teenage years, he towered over his peers. He played junior hockey in Regina, developing both his hockey skills and his willingness to fight. At 6'6", he was a target - everyone wanted to prove they could handle the big man - and Grimson quickly learned that backing down wasn't an option.
Unlike many enforcers who burst into the league as teenagers, Grimson's path to the NHL was gradual. He was drafted by the Detroit Red Wings in the 1983 NHL Entry Draft (186th overall, 10th round), but he never played a game for Detroit during his first stint with the organization.
Grimson spent years in the minor leagues, honing his craft. He played in the IHL and AHL, fighting his way through bus rides and small arenas, waiting for his chance. The call finally came in 1988 when the Calgary Flames gave him his NHL debut.
"Those minor league years taught me everything," Grimson said. "You learn patience. You learn that nothing is given to you. And you learn that if you want to make it, you have to be willing to do things other guys won't do."
The nickname emerged naturally. "Grimson" became "Grim," and with his imposing presence delivering consequences to opponents, "Grim Reaper" was inevitable. The moniker stuck, and Grimson embraced it.
"I understood what my role was," Grimson explained. "I was there to protect my teammates and make other teams think twice. The nickname reinforced that. When guys heard 'the Grim Reaper is coming,' they paid attention."
Grimson's fighting style was straightforward. He used his enormous reach to keep opponents at distance, threw powerful straight rights, and could absorb tremendous punishment without going down. He wasn't the most technically skilled fighter, but his size and determination made him one of the most dangerous.
Grimson's best years came with the Chicago Blackhawks from 1990 to 1993. In the Original Six arena, fighting in front of passionate Chicago fans, Grimson became a cult hero.
The Blackhawks of the early 1990s were a tough, physical team that made deep playoff runs. Grimson fit perfectly, providing the intimidation factor that complemented skilled players like Jeremy Roenick, Steve Larmer, and Chris Chelios.
"Chicago Stadium was special," Grimson remembered. "The building shook when we fought. You could feel the energy from the crowd. It pushed you to another level."
During his time in Chicago, Grimson faced the league's elite heavyweights: Bob Probert, Tie Domi, Marty McSorley, Tony Twist, and others. He didn't win every fight, but he never backed down - and in the enforcer world, that courage earned respect.
Any discussion of Grimson inevitably leads to his battles with Bob Probert, widely considered the toughest man in NHL history. Grimson and Probert fought multiple times over the years, with Probert generally having the edge.
"Probert was the heavyweight champion," Grimson acknowledged. "Fighting him was like fighting a force of nature. He could take your best punch and keep coming. I lost more than I won against him, but I always showed up."
The Grimson-Probert matchups became must-see events when the Blackhawks played the Red Wings. Fans knew that at some point, these two giants would square off, and the anticipation built throughout each game.
"There was respect there," Grimson said of Probert. "We were doing the same job on opposite sides. After the fights, after the games, we could shake hands. That's what people don't always understand about fighting - there was a code, and guys like Bob followed it."
After Chicago, Grimson became a journeyman, playing for eight different teams in his final nine seasons. This wasn't a sign of declining value - it was the enforcer's lot. Teams acquired Grimson for specific purposes, then moved on when those purposes were served.
His travels took him to Anaheim (twice), Detroit (a return), Hartford, Carolina, Los Angeles, and finally Nashville, where he finished his career in 2002. Each stop added to his experience and, in retrospect, prepared him for his post-hockey life.
"Playing for that many teams gave me perspective," Grimson reflected. "You see different organizations, different cultures, different approaches. It broadened my worldview in ways that staying in one place never could have."
By the time Grimson retired at age 37, he had absorbed tremendous punishment. His hands were gnarled from broken bones. His face bore the marks of countless battles. The cumulative effect of hundreds of fights - the concussions, the impacts, the trauma - had taken its toll.
Unlike many enforcers who struggled silently with the aftermath, Grimson has been remarkably open about the challenges he faced.
"There's no question fighting affected me," Grimson has said. "The headaches, the memory issues, the mood swings - they're real. I was fortunate that I had a strong support system and my faith to help me through."
Grimson has become an advocate for concussion awareness and player safety, using his platform to speak about issues that were taboo during his playing days. He's testified before government bodies and spoken at numerous forums about the need for better protection and support for players.
Throughout his career, Grimson was open about his Christian faith - unusual in a profession where religion was often kept private. He credited his beliefs with helping him navigate the contradictions of being paid to hurt people while trying to live a moral life.
"There were times I struggled with it," Grimson admitted. "You're in a job where violence is part of the deal. Reconciling that with your faith isn't easy. But I came to understand that my role was about protection, about defending my teammates. There was honor in that."
After retirement, Grimson's faith became central to his public identity. He speaks regularly at churches and faith-based organizations, sharing his journey from enforcer to believer, from ice to law.
Most hockey players face an uncertain future when their playing days end. Few have Grimson's answer: he went to law school.
In 2002, at age 37, Grimson enrolled at the University of Memphis Cecil C. Humphreys School of Law. He was older than his classmates, had a completely different life experience, and was starting from scratch in a demanding intellectual field.
"Law school was humbling," Grimson recalled. "I went from being an NHL player, where everyone knew who I was, to being a first-year law student who didn't know anything. But I approached it the same way I approached hockey - work harder than everyone else."
Grimson graduated in 2006 and passed the bar exam. The Grim Reaper had become an attorney.
Today, Grimson works as a player agent with Meyers & Partners, representing NHL players. His unique background - 14 years as a player, a law degree, and deep understanding of the enforcer's reality - makes him an effective advocate for clients.
"I've been where these guys are," Grimson said. "I understand the pressures, the lifestyle, the challenges. When I negotiate on their behalf, I'm bringing experience they can't get anywhere else."
Beyond his work as an agent, Grimson has become a sought-after speaker and commentator. He appears on hockey broadcasts, speaks at corporate events, and continues to advocate for player welfare.
Stu Grimson's legacy is unusual among enforcers. While he earned his nickname through 14 seasons of fighting, his post-career accomplishments have arguably overshadowed his playing days.
He represents what's possible when an enforcer plans for life after hockey. His story offers hope to current and former fighters who struggle with the transition - proof that the skills developed in the NHL (work ethic, discipline, resilience) can translate to completely different fields.
"I'm proud of my hockey career," Grimson said. "I did my job, I protected my teammates, I never backed down. But I'm equally proud of what I've done since. The fighting was one chapter. There are many more chapters to write."
Grimson has been thoughtful about the enforcer role and its decline in modern hockey. Unlike some former fighters who bemoan the changes, he brings a nuanced perspective.
"The game evolves," Grimson acknowledged. "We know more now about head injuries than we did when I played. It makes sense that the league is moving away from fighting. That doesn't diminish what we did - it was the job at the time, and we did it honorably."
He's also spoken about the mental health crisis affecting former enforcers. The deaths of Derek Boogaard, Rick Rypien, and Wade Belak in 2011 hit the enforcer community hard. Grimson has used his platform to encourage players to seek help and to push for better mental health resources.
"We lost too many guys," Grimson said. "Good men who were struggling and didn't know where to turn. If my voice can help one person get help, then everything I went through was worth it."
The nickname came from his last name "Grimson" and his imposing size (6'6", 240 lbs). His intimidating presence on the ice, combined with his willingness to fight anyone regardless of reputation, made the "Grim Reaper" moniker a perfect fit. The nickname was given to him early in his career and stuck throughout his NHL tenure.
After retiring from hockey in 2002, Grimson earned a law degree from the University of Memphis. He now works as an attorney and player agent, representing NHL players through Meyers & Partners. He's also become a public speaker, sharing his faith journey and advocating for player safety and mental health awareness.
Grimson had approximately 175 fighting majors during his NHL career. He accumulated 2,113 penalty minutes over 729 games. While known primarily as a fighter, Grimson also contributed 17 goals and 22 assists for 39 career points.
Yes, Grimson and Probert fought multiple times during their careers. Their battles were among the most anticipated heavyweight matchups of the 1990s. Probert generally had the edge in their encounters, but Grimson never backed down from the challenge, earning respect throughout the league for his willingness to face the consensus toughest man in hockey.
After retiring from the NHL in 2002, Grimson enrolled at the University of Memphis Cecil C. Humphreys School of Law. He earned his J.D. in 2006, passing the bar exam while transitioning from professional athlete to legal professional. He credits his faith and family support for helping him through this major life change.
