It is well documented and celebrated that on January 18, 1958, Willie O’Ree made history by becoming the first Black player to play a regular-season game in the National Hockey League as a member of the Boston Bruins, the only team to give him a shot to play at the highest level of professional hockey.
His journey can also be linked at various times with the Montreal Canadiens. O’Ree’s first contact with the Canadiens was in his Junior years, notably playing with the Kitchener Junior Canucks, a Canadiens-sponsored team. It’s while with this team that he was hit with a puck, permanently losing the sight in his right eye — a secret he kept for his entire career. He left the Canadiens system when he was signed by Punch Imlach to play minor-pro with the Quebec Aces, a Bruins farm team in the Quebec Hockey League.
His first NHL regular-season game would happen a few years later in an arena he was quite familiar with: the Montreal Forum. O’Ree had previously played there as part of the Aces against the Montreal Royals, a Canadiens-affiliated minor-pro team. The fact that his debut professional game was against the Montreal Canadiens, the team he idolized and grew up watching in the Maritimes, made the moment all the more special.
In his autobiography, O’Ree described what he felt on that night. “The lights were brighter, and the ice was brighter. The fans seemed more elegant and nobody called me any names.”
Montreal left a good impression on the professional hockey player, but unfortunately O’Ree’s first taste of the NHL was brief as the Bruins only called him up to replace a player who fell ill. After just two games, O’Ree returned to semi-pro for a prolonged stint.
In the summer of 1960, the Bruins loaned O’Ree to the Hull-Ottawa Canadiens, a Montreal farm team in the Eastern Professional Hockey League. The previous season he had played in the same league, but for Boston’s affiliate, the Kingston Frontenacs, where he scored 21 goals and added 25 assists. O’Ree played alongside future Canadiens Bobby Rousseau and Gilles Tremblay, wearing the jersey of his childhood team, but he treated it as just a stepping stone to get back to the NHL. In 16 games with the Hull Habs, O’Ree put up 19 points, of which 10 were goals, to lead the charge for a championship season for Sam Pollock’s team.
O’Ree wasn’t around to see that charge through, as a second recall to Boston and a return to the NHL loomed that season. It turned out to be significantly longer than his first stint several seasons earlier. He ended up playing 43 games for Boston in 1960-61, scoring four goals. The first goal, as fate would have it, came against the Canadiens on New Year’s Eve, 1961.
All in all, O’Ree was satisfied with his 1960-61 season, which he completed in the NHL, and had assurances from Bruins Managing Director Lester Patrick that he would be back with the team the following season. He travelled back home to Fredericton for the summer, content in knowing that his future was more or less assured. But in the sports world things can change rapidly. On May 11, 1961, Patrick traded the 26-year-old O’Ree to the Canadiens for EPHL scoring champion and rookie of the year Cliff Pennington and right-winger Terry Gray.
The Canadiens traded Pennington because he was not expected to be protected for the intraleague draft given the team’s depth at centre. The Canadiens felt that they were likely to lose him, so they wanted to at least receive some sort of return. Montreal received some firepower for their farm clubs, whether the AHL Quebec Aces or the EPHL Hull-Ottawa Canadiens. O’Ree was himself left unprotected by the Canadiens in the intraleague draft, but went unclaimed. He never did find out why the Bruins traded him.
Along with O’Ree, the Canadiens acquired Stan Maxwell, also a Black hockey player, and one of only two people who knew O’Ree’s secret about being blind in one eye. They had been the first Black players to wear an NHL jersey in a competitive game on September 20, 1957 in an exhibition match for the Bruins against the Springfield Indians at Boston Garden. Now they were both part of the Canadiens organization.
Although he would be formally joining his childhood team, O’Ree wasn’t happy about the trade, because he felt it meant the end of his time in the NHL given how stacked the Canadiens lineup was with established players at forward. The Canadiens experienced significant turnover in the off-season, watching captain Doug Harvey and Jean-Guy Gendron go to the New York Rangers, Bob Turner to the Blackhawks, and Pennington to the Bruins. However, the majority of the changes came on defence, with the forwards pretty well set, with legends Jean Beliveau, Dickie Moore, Bernie Geoffrion, Henri Richard, and Bert Olmstead among the permanent fixtures.
By early August, when Hull-Ottawa General Manager Pollock released his training camp list of 31 players who would be competing for a roster spot in September, O’Ree’s name figured prominently.
O’Ree showed up to the Hull-Ottawa training camp determined to show that he had more than just a place on the team, and right away stood out with his offensive prowess. He scored three goals during an intrasquad scrimmage, leading Pollock to call O’Ree a “sure starter” and “one of the best players on the ice.”
Despite making a strong impression, when Montreal opened their training camp in Victoria, O’Ree had not received an invitation, unlike some of the other Hull-Ottawa players like Bill Carter, John Annable, Bob Ellett, and Bill Masterton. O’Ree’s concerns were accurate; he was to be a top player for Hull-Ottawa in the EPHL, and no more.
The EPHL pre-season saw a bit of a slow start for O’Ree, who missed the first game of the season because he was hospitalized with a bad case of the flu. He returned for the second game, against the Toronto Maple Leafs, a few days later, called “the most effective Hull-Ottawan on the ice” despite probably still feeling the effects of his recent ailment. It was only in the sixth game of the pre-season calendar that he erupted, scoring three goals against the AHL’s Rochester Americans. His speed frequently allowed him to stand out from the rest of his team.
Montreal faced off against the Hull-Ottawa affiliate in pre-season game number nine in front of 6,000 people in Winnipeg in mid-October. Claude Provost, Donnie Marshall, and Gilles Tremblay scored for Montreal in a 3-1 win by the parent club, with O’Ree being the only Hull-Ottawa player capable of beating Jacques Plante. O’Ree continually made sure that the Montreal management noticed him on the ice. His goal was scored with Montreal’s top line of Richard, Geoffrion, and Marcel Bonin on the ice.
A second game against Montreal happened a week later. O’Ree once again scored for Hull-Ottawa. O’Ree was lining himself up to be one of Hull’s top players.
Unfortunately, Hull-Ottawa had a dreadful start to the season, and O’Ree along with them. By early November, despite playing on a top line, he only scored one goal and added two assists in 12 games. Fingers were being pointed, and on November 10, 1961, O’Ree’s sojourn with the Canadiens organization came to an end when Sam Pollock traded him to the Los Angeles Blades of the Western Hockey League. Pollock had announced earlier in the week that the team would be concentrating on younger players coming up through the Canadiens’ farm system, and O’Ree didn’t fit into those plans.
“I came into practice one morning, about ten after eight,” O’Ree recalled. “Sam Pollock handed me an envelope, said, ‘We traded you to the Los Angeles Blades. Here’s your plane ticket and expenses. Your plane leaves at 12:50.’”
In another account of the trade, O’Ree recalled his time with the organization: “Sammy just got off the phone with Jack Guyer, who was general manager of the Los Angeles team. The Blades were looking to get three or four players to improve their team. Sammy traded me there, but I played well for them and he treated me well, when I was with the Canadiens organization, they played me.”
O’Ree went on to find his greatest success on the west coast, playing 15 more seasons as one of the minor-pro circuit’s best players.
By breaking the NHL colour barrier, and becoming one of the trailblazers for Black hockey players everywhere, O’Ree earned his place among the most important figures in NHL history and a deserving spot in the Hockey Hall of Fame, with the Montreal Canadiens a mere footnote in his legacy.