By: Camryn Meece | Follow me on Twitter / X @MeeceCamryn
At 2:30 in the morning on September 3, 1966, an 18-year-old Bobby Orr sat aboard Boston Bruins general manager Hap Emms’ yacht on Lake Ontario. Orr was about to sign his first National Hockey League (NHL) contract with the Boston Bruins. After months of negotiation between the Bruins and Orr, with his agent Alan Eagleson, Orr signed the highest-paying rookie contract in NHL history at the time. A two-year agreement worth $70,000, plus a signing bonus, brought one of the most highly sought-after players into the Bruins franchise.
But the Bruins’ pursuit of Orr had begun years before that September night. When Orr was just 13, the Bruins started to take notice. On March 31, 1961, Bruins general manager Milt Schmidt, chairman Weston Adams Sr., and scout Wren Blair traveled to Gananoque, Ontario, to scout up-and-coming players Rick Eaton and Doug Higgins. Instead, they found Bobby Orr.
The young defenseman immediately caught the attention of the Bruins’ scouts. At just 13 years old, Orr stood out among the other players at the tournament, impressing Boston scout Wren Blair. But Boston wasn’t the only team interested. Several NHL teams had already taken notice of Orr, including the Montreal Canadiens. Scout Scotty Bowman even visited the Orr family in Parry Sound, Ontario, as teams began to show interest in him. Blair, however, became particularly determined to convince the Orr family that Boston was the right place for Bobby to continue his hockey career. He spent time getting to know the family and making his case for the Bruins. His efforts eventually paid off, and the Orr family agreed to let Bobby join the Bruins organization while he continued to develop. At 14, Orr joined the Oshawa Generals.
Over the next four seasons, he established himself in Oshawa, setting a junior record for goals by a defenseman in 1963-64 with 29 goals before breaking his own record with 34 goals the following season. By his final junior season in 1965-66, Orr was the Generals’ captain and had helped lead the team to an Ontario Hockey Association (OHA) championship and the Memorial Cup Final.
By the summer of 1966, the Bruins were working to agree on a contract with Orr and his agent, Alan Eagleson. Eagleson sought a contract that represented Orr’s value as one of the most sought-after young players in hockey. The negotiations stretched into September before the two sides finally settled on a deal.
The deal was finalized in the early hours of September 3, allowing Orr to officially join the Bruins. He made his debut on October 19, 1966, against the Detroit Red Wings and recorded an assist in Boston’s 6-2 victory. By the end of the season, Orr had recorded 41 points in 61 games and won the Calder Memorial Trophy as the NHL’s top rookie. Although the Bruins missed the playoffs again, Orr’s performance gave fans a reason to believe that the eight-year drought might finally be coming to an end.
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