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Wayne Simmonds was drawn to hockey at a young age.

He just wasn’t allowed to participate until one specific homework assignment was complete, on one specific figure.

“I remember being 6 or 7 years old, and I told my parents, ‘I want to play hockey.’ And they said before I could, I had to look up Willie O’Ree,” Simmonds, a Toronto Maple Leafs winger, told ESPN recently. “They wanted me to know why I was getting this opportunity to even be able to play the game. I did a lot of studying about Willie growing up, and ever since that, Willie has been my idol. Without him, not only Black children, but other BIPOC kids as well, probably wouldn’t have had their opportunities. Every ethnicity has its trailblazer; it’s first. Willie was the first.”

It was Jan. 18, 1958, when Willie O’Ree donned a Boston Bruins sweater and made history as the NHL’s first Black player. Because of a lifetime devoted to improving the sport he loves, O’Ree ensured he would not be the last. On Jan. 18, 2022, the Bruins will honor that legacy and their legendary alum by raising O’Ree’s No. 22 to the rafters in a long-awaited jersey retirement ceremony.

Due to a rise in COVID-19 cases throughout North America, O’Ree will have to attend the event virtually. His presence, though, could never be diminished. In speaking to those in and out of hockey that he’s inspired, his legacy will live on forever.

O’Ree’s story

O’Ree is a part of hockey lore, his story riddled with hardships overcome in the pursuit of one groundbreaking dream. Even before the Bruins initially recalled O’Ree to their ranks, he was harboring a painful secret: Just two years prior, the winger had been hit by an errant puck that left him blind in one eye. Had Boston known, O’Ree wouldn’t have been eligible for his NHL debut. The entire course of pro hockey might have changed forever.

As it was, O’Ree suited up in 45 games for Boston from 1958 to 1961, recording four goals and 14 points. His entire tenure there was marred by violence. Being the only Black player in the NHL made O’Ree a focus of vicious, racially charged attacks, from horrific slurs spewed by fellow players and fans, to targeted altercations on the ice — one of which knocked out O’Ree’s front teeth and broke his nose.

But O’Ree would not be deterred, even after he was traded to Montreal following the 1960-61 season. The Canadiens already had a stacked forward group at the time, and O’Ree had to try drawing the club’s attention during their Eastern Professional Hockey League team’s camp. His performance there was strong, but O’Ree still failed to receive an invitation to the Canadiens’ next training camp. He would never play in the NHL again.

O’Ree pivoted instead to a successful 17-year career in the minor leagues, appearing in 785 Western Hockey League games and scoring 639 points before he retired at age 43. The time O’Ree spent in the NHL was too brief, but the experience fueled his incomparable second act, leading the charge for a more inclusive hockey space.

Since 1998, the Fredericton, New Brunswick, native has been the NHL’s director of youth development and an ambassador for NHL Diversity, roles that put O’Ree face-to-face with the generations of players his work is impacting.

That vision O’Ree holds for a better hockey community has resulted in numerous awards and honors over the years, one of the largest being his enshrinement by the Hockey Hall of Fame’s Builder category in 2018. It’s also what earned O’Ree the Order of Canada — that country’s highest civilian honor — in 2008. And it’s why the 116th U.S. Congress is bestowing the United States Congressional Gold Medal to O’Ree this year. At 86 years old, O’Ree’s passion for his cause remains unchanged.

That’s all the more impressive considering O’Ree never chose to be a pioneer. He didn’t ask to bear that burden, to have been one of one. But O’Ree met the challenge, while creating space for more minority players in the hockey world. For those like NHL Players’ Association agent Eustace King — O’Ree’s own longtime representative — who has traveled the road O’Ree paved. To write their own stories.

“If it wasn’t for Willie O’Ree, there would be no Black executives in the National Hockey League like myself. There wouldn’t be any Black players,” King said. “And if there were, it would have been [much] later on. But [what he went through] really opened up everyone’s eyes, and I think that because of his personality and character, he was able to handle it.”

Inspiring younger generations

Anthony Stewart has the photo hanging in his office.

It’s from 2003, and Stewart had just been drafted by the Florida Panthers. He had exchanged pleasantries with commissioner Gary Bettman, pulled on that traditional jersey/hat combo, and was exiting the stage when O’Ree came into sight. Their interaction was short but meaningful, and remains memorialized on Stewart’s wall.

“He was going above and beyond to make sure he was meeting all the minority draft picks,” Stewart recalled. “So just to have him be a part of that day was definitely special. I still remember it. I have the picture of us framed. It just showed he cares about growing the game, he cares about the game of hockey. I’ve definitely looked up to players like Willie, who was the first.”

A decade later, O’Ree was still waiting in the wings to greet NHL draftees. Anthony Duclair recalls being selected by the New York Rangers in 2013 and sharing a “really cool moment” right after with O’Ree and fellow draftee Jordan Subban.

“It was just a time where I was in awe, to be honest,” Duclair said. “He’s just meant a lot and touched so many people’s lives. I remember [we talked about] working hard and being yourself. I really took those words to heart, about just being yourself. Don’t try to be someone else to please other people. Just work hard and have fun. That was his message.”

Subban arrived at draft day inspired by his older brother, New Jersey Devils defenseman P.K. Subban, already making inroads through the NHL. But meeting O’Ree that first time was something special for the younger Subban, cementing his beliefs about what was possible for his own future.

“Willie O’Ree was a tremendous role model,” Subban said. “I looked at him as almost a symbol of being able to accomplish your dreams, no matter what the circumstances. I think especially nowadays, there’s a lot more talk about some of the barriers that Black players have to go through playing hockey. When he was able to break the color barrier in the NHL, those barriers were most likely significantly worse. He’s someone that I look up to as [an example] to just keep pushing forward.”

Blake Bolden can attest to O’Ree’s power in that respect. It was his influence that motivated Bolden to blaze her own trail, as the first Black player to compete in the National Women’s Hockey League, and the first Black female pro scout for the Los Angeles Kings.

“Willie has been an integral part of my life and journey as a Black professional hockey player,” she said. “His words have fueled me to be the best version of myself and give back to the game. He is a legend, a trailblazer and inspiration. His legacy will continue to transcend the sport of hockey as an icon for true diversity, equity and inclusion.”

O’Ree has always been more than another handshake; he’s become a great friend to many mentees. Simmonds was also introduced to O’Ree after being drafted by Los Angeles in 2007; now they share an agent in King and speak often. A lot has changed over the years since then for Simmonds, as a player and a person, but he has stayed close with O’Ree and learned myriad lessons from him in the process.

“The thing I’ve taken from Willie the most is just his humility,” Simmonds said. “After everything he’s gone through, and that he’s faced, I’ve never met a more humble man. After what the game put him through, I don’t know anyone else who would want to give back to it as much as Willie has. Willie has been a pillar in the hockey community and for players who look like myself since he broke into the NHL. He’s a trailblazer. He’s an astronaut in my eyes. Without Willie, it wouldn’t be a possibility for me to be where I am.”

The Jackie Robinson of hockey

“For me, Willie was just as big as Jackie Robinson,” Simmonds said. “I think he should be viewed that way throughout the whole sports world. I’m a big believer in if you don’t know where you’ve come from, you don’t know where you’re going to go. I took that to heart with Willie.”

It’s virtually impossible for those players most impacted by O’Ree’s legacy not to mention Robinson in the same breath. Both were icons in their respective arenas for doing what no one else had, and over time they changed the perception of what players at the highest level would look like.

“Willie’s the Jackie Robinson of hockey,” said Minnesota Wild defenseman Matt Dumba. “Breaking down the barriers that he did, being that name, that player of color, to look to him as the first person that ever did it. He made it possible for minorities to play in the league. It just is really special, because that representation definitely matters, and to know that he did it in a different era and knowing what he went through during those times? It’s just incredible; it was a whole different time in the world.”

Stewart admits it was harder at 18 to appreciate what O’Ree endured during his early life. Now, being 37 years old and having experienced his own obstacles on and off the ice, Stewart can better understand O’Ree’s past.

“Just imagine how bad Willie had it at that time, being the first and only Black hockey player,” Stewart said. “That puts things in perspective when you have guys that trailblazed and paved the way to make it easier for players. He should be in the same conversation as Jackie Robinson. You see how beloved Jackie is, and that should be the equivalent of [Willie] in hockey. 2,000 years from now, when they dig up the archives of what hockey was or what hockey is, Willie’s story and plight should be there with all the other stories as well.”

In the five decades since O’Ree’s debut, more than 100 non-white players have appeared in NHL games. But the league remains approximately 97% white. That imbalance has led to initiatives like the NHL’s “Hockey Is For Everyone” striving to spread a message of inclusion. The Hockey Diversity Alliance has taken it a step further, launching its own messaging to not only highlight racism that is still prevalent in the league, but calling out white allies to amplify their voices.

“We talk about a sense of loneliness [being a player of color] among your own teams now,” Dumba said. “But Willie was the only one in the entire league. So, I think that’s just an incredible feat, and we’re all very proud of him. He’s a legend. He will always be a legend in every way, just being able to break down that color barrier. He’s been a beacon of hope.”

That’s what O’Ree was, in part, to a young Mark Fraser. Years before Fraser was drafted by the Devils in 2005, he was absorbing the stories of great Black athletes who would eventually inspire his own 200-plus game NHL career.

“My first book report at a very young age was on Jackie Robinson. And being a Canadian kid and a hockey lover and hockey player, I had a similar interest in learning the story of Willie O’Ree,” Fraser said. “Just celebrating Black excellence and the overcoming of adversities and doing it with such elegance and grace is something that I’ve always really admired with Willie.”

Fraser hasn’t met O’Ree in person, but his journey has been indelibly marked by O’Ree’s contributions to the sport. Like Dumba, Fraser can recall a sense of isolation in NHL dressing rooms, of not feeling empowered to speak up against “daily microaggressions” that still exist. At the same time, Fraser knew he wasn’t truly alone in that battle. O’Ree had tackled it first, to make the road ahead easier on others.

“His legacy is so much bigger than what he did on the ice,” Fraser said. “And that stuck with me. If Willie was able to get through [these challenges] in a time which I can only believe was tougher to be resilient and to overcome than the generation that I grew up in, then that 100 percent empowered me and encouraged me to not let a racial epithet or whatever you’re potentially dealing with to win and not let it overcome you and to not succumb to it.”

‘We will never let his name die’

Bryant McBride knows about conquering a challenge. He’s a successful film producer and businessman, and was the first Black class president at West Point.

But nothing could prepare McBride for just taking a walk with O’Ree.

“One of the hardest things I’ve ever had to do is go through an NHL arena with Willie O’Ree,” said Bryant. “Because there’s 10,000 people coming up to him. I can’t even begin to tell you how many people he’s met that love him, that just will do anything for him. Because he would do anything for so many people. It’s Willie’s personality, it’s his love for the game and his passion to include everybody. That’s his magic.”

McBride captured that essence in the sports documentary “Willie,” and he reflects fondly on what the experience taught him about O’Ree’s legacy. He recalls going to O’Ree’s house and seeing his Order of Canada award on the wall, next to his plaques for earning employee of the month from a security guard job. To O’Ree, all work is equal. All work has value.

“What sets him apart? It’s that while it is really so easy to be bitter, Willie is just all about providing opportunities looking forward,” McBride said. “He’s not looking back. He’s lived through that and it’s hard, and it was still fun and he’s talked about it at length with real candor, but he’s looking forward. And asking: How do we make it better? That’s his mantra, and it has served him well.”

It’s a journey O’Ree seems destined to travel until, well, he can’t anymore. Even at the pinnacle of a career for most people — being inducted into the Hall of Fame — O’Ree was wondering, what’s next?

“One of the last things that he said [at the Hall of Fame] was, ‘My job is not finished; I still have plenty of things to do and accomplish,'” King said. “And he was talking about things that he was doing with the NHL programs. He wanted to make sure he helped kids and traveled [the world] to make sure he got the message across. To me, that’s his lasting legacy. He did break the color barrier. He basically integrated the sport of hockey, he’s the one that did it. And he was a hell of a hockey player as well.”

That’s where it all started for O’Ree, with a pure love of the game. Raising his jersey in Boston will acknowledge all for which O’Ree has stood: One person destined to change the lives of many.

“I think he’ll be remembered just as a man who, in my eyes, went through a ton even just to get to the NHL, but he didn’t stop there,” Simmonds said. “He continued on, and he continues to push for more equality and for other people who look like him to be able to play this game and enjoy this game.

“We will never let his name die. It will never die; I can tell you that.”