Orr started in organized hockey at age eight. He first played as a forward, but moved to defence and was encouraged to use his skating skills to control play. Orr's play in Ontario provincial competition attracted the notice of NHL scouts as early as age twelve. At fourteen, Orr joined the Oshawa Generals,[4] the Bruins' junior hockey affiliate, and he was an all-star for three of his four seasons.
In 1966, Orr joined the Boston Bruins, a team that had not won a Stanley Cup since 1941 and had not qualified for the playoffs since 1959. With Orr, the Bruins won the Stanley Cup twice, in 1970 and 1972, and lost in 1974. In both victories, Orr scored the clinching goal and was named the playoff MVP. In the final achievement of his career, he was the MVP of the 1976 Canada Cup international hockey tournament. In 1976, Orr left Boston as a free agent to join the Black Hawks, but repeated injuries had effectively destroyed his left knee, and he retired in 1978 at age 30.
Orr's first professional contract was one of the first in professional ice hockey to be negotiated by an agent. It made him the highest-paid player in NHL history as a rookie. His second contract was the first million-dollar contract in the NHL. However, after his retirement, Orr learned he was deeply in debt and he had to sell off most of what he owned. Orr broke with his agent Alan Eagleson and sued the Black Hawks to settle his contract. Orr and his family returned to Boston where Orr went into business to rebuild his finances. Orr aided the investigations that led to Eagleson's fraud convictions and disbarment. Orr also supported a lawsuit that challenged the NHL over its control of its pension plan.
After his hockey career, he became a scout for several professional teams. Orr entered the player agent business in 1996 and was the president of the Orr Hockey Group agency, until its acquisition by the Wasserman Media Group in 2018. Orr is also active in charitable works and in television commercials. Since 1996, Orr has coached a team of junior hockey players in the annual CHL Top Prospects Game.
Career achievements:
Despite playing only twelve seasons and 657 games (of which only his first nine seasons, totalling 621 games, were full seasons), and only playing 47 NHL games after his 27th birthday, Orr accomplished many records and achievements, a number of which still stand today, and are listed below.
As of the end of the 2018–19 season:
- First and only defenceman to score nine hat tricks.
- Only defenceman to win the Lester B. Pearson Award.
- Only player ever to win the Norris Trophy, Art Ross Trophy, Hart Trophy, and Conn Smythe Trophy in one season (1969–70)
- Only defenceman to win the Art Ross Trophy as league leader in scoring (1969–70, 1974–75)
- First defenceman to score 30 goals (1969–70) and 40 goals (1974–75) in a season.
- First player to record 100 assists in a season (1970–71)
- Highest single season plus-minus rating, +124 in 1970–71.
- Second all-time in career plus-minus rating (+597; retired as the overall leader)
- Never finished a full season less than +30 since +/- became a statistic (beginning with the 1968–69 season)
- Fourth in league history in career point-per-game average, all-time, (1.393) (highest among defencemen, minimum 500 career points).
- Sixty-sixth overall in league history in career assists and tied for 109th in career points.
Awards:
- OHA first All-Star team – 1964, 1965, 1966
- Awarded the Calder Memorial Trophy (rookie of the year) in 1967, the youngest ever to win the award, and the youngest ever to win a major NHL award up to that time.
- Named to the NHL second All-Star team in 1967 (his only full season when he did not make the First Team, as a rookie)
- Played in the NHL All-Star Game in 1968, 1969, 1970, 1971, 1972, 1973, 1975
- Named to the NHL first All-Star team in 1968, 1969, 1970, 1971, 1972, 1973, 1974, 1975
- Won the James Norris Trophy in 1968, 1969, 1970, 1971, 1972, 1973, 1974, 1975
- NHL Plus/Minus leader in 1969, 1970, 1971, 1972, 1974 and 1975, the most in history.
- Won the Art Ross Trophy in 1970 and 1975
- Won the Hart Memorial Trophy in 1970, 1971, 1972
- Awarded the Conn Smythe Trophy in 1970 and 1972, the first two-time winner of the playoff MVP award
- Stanley Cup champion in 1970 and 1972
- Won Lou Marsh Trophy as Canadian athlete of the year in 1970
- Received Sports Illustrated magazine's "Sportsman of the Year" award in 1970
- NHL All-Star Game MVP in 1972
- Voted the greatest athlete in Boston history in the Boston Globe newspaper's poll of New Englanders in 1975, beating out baseball and basketball stars such as Ted Williams, Bill Russell, Carl Yastrzemski and Bob Cousy.
- Awarded the Lester B. Pearson Award in 1975
- Named the Canada Cup Tournament MVP in 1976
- Awarded the Lester Patrick Trophy in 1979
- His #4 Jersey was retired by the Boston Bruins on January 9, 1979.
Records:
- Most 100-point seasons by a defenceman (1969–70 to 1974–75).
- The only player to win four major NHL awards in one season (Hart, Norris, Art Ross, and Conn Smythe in 1970), as well as the only player to win the Norris and Art Ross in the same season.
- Fastest goal from start of overtime to clinch the Stanley Cup (0:40; 1970, game 4)
- Most points in one NHL season by a defenceman (139; 1970–71)
- Most assists in one NHL season by a defenceman (102; 1970–71).
- Highest plus/minus in one NHL season (+124; 1970–71)
- Most assists in one NHL game by a defenceman (6; tied with Babe Pratt, Pat Stapleton, Ron Stackhouse, Paul Coffey and Gary Suter)
International play: