Bobby Orr

Bobby Orr displayed his hockey talents from an early age. Orr played his first organized hockey in 1953 at age five, in the "minor squirt" division, a year after getting his first skates and playing shinny. Although he was tiny and somewhat frail, he soon was able to skate faster than anyone his own age, speed he demonstrated in races around the rink and in games. Until he was ten years old, Orr played on the wing, as a forward. His coach, former NHL player Bucko McDonald, moved Orr to defence. Although Orr played defence, McDonald encouraged Orr to use his talents as a stickhandler, skater and scorer to make offensive rushes. According to McDonald: "I used to tell Doug the kid was in his natural position when he played defence. You didn't have to be genius to see that – honest. I don't think Doug agreed, but he accepted my decision." Orr would later credit McDonald: "Bucko taught me almost everything I know."

By the time Orr turned 16 in 1964, he was still two years away from playing in the NHL and his father Doug was dissatisfied with the Bruins' treatment of the prospect. Doug had asked the Bruins' Blair for more money for Bobby and was turned down. Doug Orr met Toronto lawyer Alan Eagleson at a juvenile fastball tournament dinner in Parry Sound and asked Eagleson to help out with the situation. Eagleson agreed to work with the family for free and continued to do so for the next two years. Bobby and Eagleson developed a relationship Orr would later describe as being like brothers. The two soon became a team, discussing Bobby's future plans without his father Doug.

Oshawa's hopes in the 1966 Memorial Cup Final were damaged when Orr suffered a groin injury against Shawinigan, an injury that is painful and weakens a player's skating ability. To promote the event, held in Toronto's Maple Leaf Gardens, the Generals had advertised it would be the last chance to see Orr in junior and were anxious for him to play. Bruins' management demanded Orr not play in the Final, not wanting to risk further damage to their property. Orr and his parents, however, were adamant he be allowed to play for the national championship. As he had not signed to the Bruins, they threatened he would never play for Boston if he was held out. Blair decided to defy the Bruins' ownership and let Orr play. While Orr dressed and played some, he was not a factor and Edmonton defeated Oshawa for the Cup. Oshawa coach Bep Guidolin was fired for letting Orr play, while Blair left the organization of his own accord to join the expansion Minnesota North Stars.

Orr joined the Bruins for the 1966–67 season, his first as a professional. The Bruins were not convinced Orr belonged on defence, trying him out at centre first. Through the pre-season, Orr was given jersey number 27. With Orr's junior number (2) retired in honour of Eddie Shore, the Bruins offered him jersey number 5, that of past Bruins star Dit Clapper, prior to the regular season. But Orr instead chose jersey number 4, which had been vacated by veteran defenceman Albert Langlois. Orr made his NHL regular-season debut on October 19, 1966, against the Detroit Red Wings, getting one assist. On October 22, he scored his first NHL goal against the Montreal Canadiens. It was a slap shot past Gump Worsley and the Boston Garden crowd gave Orr a standing ovation.

In that first season, Orr was challenged by the veterans, and he earned respect by defeating Montreal tough guy Ted Harris in his first NHL fight. On December 4, 1966, Toronto Maple Leafs' defenceman Marcel Pronovost checked him into the boards, injuring Orr's knees for the first time in the NHL. He would miss nine games and the Bruins would lose six of them. The team finished with a 17–43–10 record, leaving the Bruins in last place. However, attendance at Boston Garden increased by forty-one thousand fans.

Orr was also known for his mean streak. Former coach Don Cherry recounts an incident one night in Los Angeles during a game that the Bruins were losing. With a minute to go, Orr pulled one of the Bruins off the ice, left the bench and attacked a Los Angeles Kings player. Asked why, Orr said to Cherry "He was laughing at us." According to Cherry, he fought a lot. On another occasion in November 1967, Orr was clipped in the face by a stick from the Toronto Maple Leafs' Brian Conacher. Boston teammate Johnny McKenzie flattened Conacher from behind and started punching Conacher. Orr, cut and bleeding, got up from the ice, pulled MacKenzie off Conacher and started punching Conacher. Conacher, who was not fighting back, was also sucker-punched by the Bruins' Ken Hodge. Orr would be booed in Toronto from that date onwards. Orr was frequently compared to Brad Park, who played a similar style to Orr and later succeeded Orr as Boston's top defenceman, and the two often fought each other on-ice, fuelling the bitter rivalry between the Bruins and New York Rangers. Park said "I saw no reason to be upset because I was rated second to Bobby Orr. After all, Orr not only was the top defenceman in the game but he was considered the best player ever to put on a pair of skates. There was nothing insulting about being rated number two to such a super superstar".

Orr went on to lead the Bruins in a march through the 1970 playoffs scoring nine goals and 11 assists. The march culminated on May 10, 1970, when he scored one of the most famous goals in hockey history and one that gave Boston its first Stanley Cup since 1941. The goal came off a give-and-go pass with teammate Derek Sanderson at the 40-second mark of the first overtime period in the fourth game, helping to complete a sweep of the St. Louis Blues. According to Orr:

In 1970, Orr received the Golden Plate Award of the American Academy of Achievement. In 1979, Orr was invested as an officer in the Order of Canada. Two buildings in his hometown of Parry Sound are named after Orr. The first is the Bobby Orr Hall of Fame, where his Order of Canada medal is on display along with other exhibits. The second is the Bobby Orr Community Centre, a multi-purpose entertainment facility. In 1995, Bobby Orr was inducted into the Ontario Sports Hall of Fame. Orr has been honoured with a star on Canada's Walk of Fame in Toronto. In 2004, an elementary school in South Oshawa named after Orr opened. On November 27, 2008, the Oshawa Generals retired Orr's number 2 jersey; the Generals had not issued the number since Orr transferred to the NHL in 1966. Orr thanked all who helped him in the four years he played in Oshawa: "I did a lot of growing up in Oshawa from ages 14 to 18 and I'll be forever grateful for those people who helped me in that time of my life." In February 2010, Orr was one of the eight bearers of the Olympic flag at the Opening Ceremonies of the 2010 Vancouver Olympics.

Orr signed a new five-year contract on August 26, 1971, for US$200,000 (US$1,262,613 in 2019 dollars) per season – the NHL's first million dollar contract. In the following 1971–72 season, Orr was again second in the scoring race to Esposito, this time with 117 points, as his goal total matched his previous years total of 37 but his assists dropped to 80. He again won the Hart and Norris trophies, helping the Bruins to a first-place finish in the East. In the 1972 playoffs, Orr again led the Bruins to the Stanley Cup, leading the scoring in the playoffs (24 points with 19 assists) and scoring the championship-winning goal against New York. For his performance in the playoffs, he received his second Conn Smythe Trophy as playoff MVP, making him the award's first two-time winner. Rangers forward Vic Hadfield commented "We played them pretty even, but they had Bobby Orr and we didn't." By this time, Orr knew his left knee was deteriorating and he would not have many seasons left. Orr also won the MVP award at the 1972 NHL All-Star Game to win three MVP awards in one season.

While on vacation, Orr met Margaret Louise "Peggy" Wood, a Trenton, Michigan native and speech therapist who worked in Fort Lauderdale, Florida. They became engaged on Christmas Day, 1972, and married in September 1973 at a 'secret' ceremony in Parry Sound. They have two sons, Darren and Brent. Darren works as a player's agent at Orr Hockey Group. Orr's mother Arva died in November 2000, 18 months after being diagnosed with cancer. Orr's father Doug died in 2007. Orr became a grandfather when granddaughter Alexis was born in 2009. A second grandchild, Robert, was born in January 2011.

The 1972–73 saw upheaval at the Bruins. Former head coach Sinden returned to the club as the general manager. Bruins players Gerry Cheevers, Derek Sanderson and Johnny McKenzie joined the upstart World Hockey Association. Coach Tom Johnson was fired fifty-two games into the season, replaced by Bep Guidolin, who had once coached Orr. The Adams family, which had owned the team since its founding in the 1920s, sold it to Storer Broadcasting. The Bruins' season came to a premature end in a first-round loss in the 1973 playoffs, losing Esposito to injury in that first round. Orr amassed 101 points during the regular season (he only played 63 games due to injury) but had only two points in the playoff loss.

The 1975–76 season was Orr's final season with the Bruins and it was tumultuous. Orr's contract was ending after the season, potentially making him a free agent. The Bruins were sold by Storer Broadcasting in August 1975 and the new Jacobs ownership group had to promise to keep Orr as a condition of the purchase. The Bruins and Orr reached a verbal agreement with the Jacobs during the summer of 1975, including a controversial agreement for Orr to take an 18.5% share of the Bruins after his playing days were over. The agreement was to be checked out as to whether it would be legal for tax reasons and whether or not the league would approve it.

Before the season started, however, Orr underwent another surgery on September 20, 1975. The Bruins' contract talks with Orr and Eagleson became difficult. The Bruins' insurer would not insure a contract with Orr and doctors advised the Bruins that Orr would not be able to play much longer. Orr returned to the line-up on November 8, 1975, the day after the Bruins traded Esposito to the New York Rangers. Orr was able to play the next ten games for the team but had to stop on November 28 due to pain in his knee. The next day, he underwent another knee surgery. Originally expected to only be out for seven to eight weeks, his knee did not respond to therapy and he returned home to Parry Sound. His season was over after ten games and he would not play again for the Bruins. His impending free agency led to speculation that the Bruins would trade him, but despite his injury, they were negotiating to keep him until the end.

In September 1975, the Bruins and Eagleson had reached a deal that would pay Orr US$4 million (US$19,005,566 in 2019 dollars) for ten years. But when Orr's knee required surgery, the Bruins reduced its offer to US$295,000 (US$1,325,430 in 2019 dollars) per season and a payment of US$925,000 (US$2,870,265 in 2019 dollars) or 18.6% of the Bruins in June 1980. Eagleson turned down the offer and on June 7, 1976 was quoted in the Toronto Star as saying "Boston offered a five-year deal at US$925,000 or 18.6 per cent ownership of the club in 1980. I didn't think it would be wise for him to be a player-owner." On June 9, 1976, after Orr had signed with Chicago, Eagleson told The Globe and Mail that the Bruin offer was "a five-year offer for US$295,000 a year. In addition, Orr was to receive US$925,000 in cash payable in June 1980. That was to be a cash payment or involve Orr's receiving 18.6 per cent of the Bruins stock." According to a famous 1990 story in the Toronto Star by Ellie Tesher, Orr stated that Eagleson never told him of the offer, during negotiations or after. While Eagleson had spoken publicly to reporters of the offer, he had not discussed it with Orr.

In 1976, the Bruins offered Orr US$600,000 (US$2,695,789 in 2019 dollars) per season, but he would have to pass a physical examination at the start of each season's training camp. Only the first year's money was guaranteed. Eagleson was quoted at the time as saying, "There is only one way that Bobby Orr will ever be back with the Bruins. And that's if Jeremy Jacobs asks him for another meeting and straightens out the whole situation. Otherwise he's gone." Instead, Orr became a free agent, with Boston to receive compensation. Orr and Eagleson whittled down a list of potential teams to St. Louis and Chicago. Chicago offered a five-year guaranteed contract with the Black Hawks, and on June 8, 1976, he officially signed with the Black Hawks. The Bruins' general manager, Harry Sinden complained of tampering by the Black Hawks, and demanded that Chicago owner Bill Wirtz submit to a lie detector test. According to documents held by Orr, they had a valid case. Orr signed with the Black Hawks at a secret meeting in May 1976, prior to becoming a free agent.

After Orr signed with Chicago, the Black Hawks gave him permission to play for Team Canada in the 1976 Canada Cup tournament. Orr did not play in the 1972 Summit Series against the Soviet Union, and he wanted badly to play for Canada. Orr had been unable to play in the Summit Series due to knee surgery, although he did participate as a non-player. Orr's participation in the Canada Cup was considered ill-conceived and Eagleson later thought it may have been the 'last straw' that killed his career. Orr himself said that he knew before the tournament that "I knew I didn't have much longer. That series didn't do it. I thought I could get the next season in, but not much after that. I knew, looking at that team, I wouldn't have to do as much. I wouldn't have traded it for anything."

Orr signed with Chicago, but his injuries limited him to only 26 games over the next three seasons. He sat out the entire 1977–78 season. By 1978, Orr had undergone over a dozen knee surgeries, was having trouble walking and barely skated any more. However, in the summer of 1978, he decided to make a comeback. He played six games of the 1978–79 season and came to the conclusion that he could no longer play and informed the Black Hawks that he was retiring. He started a new role as an assistant to Chicago general manager Bob Pulford. He scored his last NHL goal and point against Detroit on October 28, 1978, at Detroit's Olympia Stadium.

His number 4 jersey was retired by the Bruins on January 9, 1979. At the ceremony, the crowd at Boston Garden would not stop applauding and as a result, most of the evening's program had to be scrapped at the last second due to the constant cheering. The crowd did not allow Orr to say his thank you speech until he put on a Bruins jersey. The day was proclaimed "Bobby Orr Day" in Boston and the event raised thousands of dollars for charity. He attended the Massachusetts Senate and House of Representatives and was given a five-minute standing ovation. Boston Celtics basketball superstar Larry Bird said in his pre-game inspiration that he always looked up at the rafters of the Garden at Orr's retired No. 4, instead of the retired numbers of Celtics stars such as Bill Russell, Bob Cousy, or John Havlicek.

Then-Bruins head coach Don Cherry suggested that the reason Orr never re-signed with the Bruins was Orr's complete trust in Eagleson at the time (Orr said that he described Eagleson as a brother). Cherry recalled Orr had refused to speak with the Bruins team president directly, allowing Eagleson to mislead or withhold enough details from Boston's offer. Orr's departure from the Bruins was acrimonious and he has not held an official role with the Bruins since. Years later, it emerged that Eagleson had very good relations with Black Hawks owner Bill Wirtz and NHL president John Ziegler that colluded to hold back salaries of certain players. Orr disassociated himself from Eagleson in 1980.

Shortly after Orr retired, an independent accountant revealed that Orr's liabilities exceeded his assets, leaving him essentially bankrupt despite being supposedly one of the highest-paid players in the NHL. As well, Orr's taxes were under review. Eagleson had set up a corporation to receive Orr's income and pay Orr a salary, but the arrangement was rejected by US and Canadian tax authorities. His assets in July 1980 totalled US$456,604 (US$1,608,477 in 2019 dollars) and his tax, legal and accounting bills totalled US$469,546 (US$1,654,068 in 2019 dollars). Eagleson, who had once said Orr was 'fixed for life', criticized Orr for 'living beyond his means' and ignoring his investment advice. Orr split with Eagleson on April 1, 1980. As part of the legal settlement with Orr, Eagleson agreed to purchase various assets of Orr's for US$620,000 (US$1,923,853 in 2019 dollars), including his Orr–Walton Hockey Camp, which paid off US$450,000 (US$1,396,345 in 2019 dollars) of Orr's bank loans.

Orr later played a role in the exposure of Eagleson's misconduct over the years. He had once considered Eagleson a "big brother", but broke with him in 1980 in part because he suspected that Eagleson had not been truthful with him. In addition to misleading his clients about contract terms, Eagleson fraudulently used NHLPA funds to enrich himself. Orr was one of several players who filed a formal complaint of legal misconduct against Eagleson with the Law Society of Upper Canada over Eagleson's lending of trust monies without the consent or knowledge of his clients. In 1998, Eagleson was convicted of fraud, embezzlement and racketeering. After the conviction, Orr was one of eighteen former players who threatened to resign from the Hockey Hall of Fame if Eagleson was not removed as a builder. Facing almost certain removal, Eagleson resigned instead.

Orr is also well known for his charitable works, although he kept mention of them out of the press. Former Eagle-Tribune writer Russ Conway noted of one occasion when Orr and Conway visited Boston Children's Hospital, with a box of programs, pennants, pucks, pictures and Boston memorabilia: "We went from room to room, Orr popping in, unannounced to visit the kids. Some couldn't believe their eyes; sick as they were, they laughed in astonishment and delight. Bobby Orr! He talked and joked with every one of them, asking names, rubbing heads, giving everybody a little present from the box, leaving a stick, autographing everything in sight." Orr made Conway promise to not print a word in the newspaper. Orr was involved in numerous charity fund raisers. In 1980, Orr was awarded the Multiple Sclerosis Silver Hope Chest Award by the Multiple Sclerosis Society for his "numerous and unselfish contributions to society".

Orr served briefly as an assistant coach for Chicago, and as a consultant to the NHL and the Hartford Whalers. The Black Hawks balked at paying him the balance of his contract, and Orr took them to court, settling in 1983 for US$450,000 (US$1,155,145 in 2019 dollars), one-third of the money they owed him. Of this, US$200,000 (US$513,398 in 2019 dollars) went to taxes and legal fees. Orr moved back to the Boston area and formed Can-Am Enterprises with partners Tom Kelly and Paul Shanley, which built up a clientele of endorsements for Orr, including Baybank and Standard Brands. Orr did eventually restore his finances, thanks to endorsement contracts and public relations work.

Orr was also involved in the 1991 lawsuit of retired NHL players against the NHL over its control of the players' pension fund. Eagleson was involved there too, arranging for the players to give up a seat on the trusteeship of the pension fund in 1969 to gain the acceptance of the NHLPA with the NHL owners. Orr and ex-Bruin Dave Forbes discussed the lawsuit with the sports newspaper The National. Orr: "Our money is being used to pay pensions for current players". The NHL's response was to file a notice of libel and slander against Orr and Forbes. Carl Brewer defended Orr in a letter to then-NHL president John Ziegler: "It is regrettable that the NHL and the member clubs would resort to such treatment of one of our game's icons, Bobby Orr. And isn't it interesting that baseball players who started their pension plan in 1947, as did the NHL, have assets in their plan of some US$500 million while we, as far as we can understand, have US$31.9 million." The pension lawsuit was finally won by the players in 1994 after two courts ruled against the NHL. The NHL had appealed the case to the Supreme Court of Canada which decided not to hear the case.

Orr has been known to be fiercely loyal to former Bruin personnel and teammates. When Derek Sanderson had alcohol and prescription drug-abuse problems and wound up penniless, Orr spent his own money to ensure that Sanderson successfully completed rehab. Decades later, Orr and Sanderson went into business together managing finances for hockey players. Orr also helped out Bruins trainer John (Frosty) Forristall, his roommate during his first years with the Bruins, who had just been fired from the Tampa Bay Lightning for alcoholism in 1994. Forristall's drinking put him on bad terms with his brother John, so he returned to Boston jobless and soon afterwards was diagnosed with brain cancer. Orr took Forristall into his home for a year until he died at the age of 51. Orr was a pallbearer at his funeral.

Orr became an agent representing hockey players in 1996. Along with investors, Orr purchased the Woolf Associates agency founded by Boston lawyer Bob Woolf. To prevent conflicts of interest, Orr sold an investment in the Lowell Lock Monsters minor pro hockey team and cut his ties with a credit card firm that had a contract with the NHLPA. Orr became a certified agent, although he would not be negotiating with hockey clubs. Player agent Rick Curran merged his agency with Orr's in 2000. Curran and Orr along with partner Paul Krepelka incorporated the agency as Orr Hockey Group in February 2002.

For the season, the Bruins gave Orr a solid gold puck, one of four they gave out to Bruins players – to each of the four Bruins who scored over 100 points that season – Esposito, Orr, Johnny Bucyk and Ken Hodge. Orr later gave his puck to Alan Eagleson. In 2007, Eagleson sold the puck in an auction of memorabilia for CA$16,500.

Orr's style of play was hard on his left knee, leading to injuries and surgeries that shortened his career. The left knee took all of the punishment and was operated on "13 or 14" times according to Orr. Orr was a left-hand shot who played the right side. He would race down the right wing with the puck and attempt to beat the opposing defenceman using his speed and strength. He 'protected the puck', leading with his left knee, and holding his left arm up to fend off opponents. This put him into a position where a hit by the opposing defencemen would often hit the left knee. Also, he would often end up crashing into either the opposing goalie, the net or the end boards. "It was the way I played," Orr has said. "I liked to carry the puck and if you do that, you're going to get hit. I wish I'd played longer, but I don't regret it." Orr stated in 2008. "I had a style—when you play, you play all-out. I tried to do things. I didn't want to sit back. I wanted to be involved."

His right knee was basically undamaged during his career; his left knee looks like "a road map of downtown Boston" according to sportswriter Bob McKenzie. His left knee was used in a MasterCard commercial in 2008, his scar lines used in an animation connecting his many achievements to the year of the individual scar line. According to a 2009 Sports Illustrated article Orr has since had two knee replacement surgeries that have left him pain-free.

A bronze statue of Orr stands next to Boston's TD Garden, the Bruins' home arena. It was unveiled on May 10, 2010, the 40th anniversary of the Bruins' first Stanley Cup victory with Orr, and depicts him immediately after scoring the winning goal. The unveiling ceremony was attended by Orr and several of his former teammates. Orr said of the statue at the ceremony, "This specific moment and time we celebrate with this statue is something we can all now nostalgically remember with fondness, together, each time we enter Boston Garden. To all of you, thank you very much from the bottom of my heart. I'm honoured. Guys, thank you." In 2012, he received the Queen Elizabeth II Diamond Jubilee Medal.

On November 3, 2013, Orr's long-awaited autobiography titled Orr: My Story, debuted at the #8 position on The New York Times best seller list for nonfiction.

Since retiring, Orr has performed a number of ceremonial first puck drops with the Bruins, including at the 2010 NHL Winter Classic with Bobby Clarke, between the Bruins and the Flyers. Orr performed another ceremonial puck drop on October 20, 2016, Orr along with Milt Schmidt dropped the ceremonial puck at the Boston Bruins' first home game of the season.

Orr was noticed by the Boston Bruins in the spring of 1961, playing in a youth hockey tournament in Gananoque, Ontario. The Bruins' Wren Blair described him as "a combination of Doug Harvey and Eddie Shore." The Bruins immediately pursued Orr. Blair made regular visits to the family home. In the fall of 1961, the Bruins invested CA$1,000 (CA$8,497 in 2018 dollars) to sponsor his minor hockey team. Although three other NHL teams (Toronto Maple Leafs, Detroit Red Wings and Montreal Canadiens) were interested in Orr, he signed in 1962 with the Bruins. Orr explained that he signed with the Bruins because "they're a team of the future. They're rebuilding and I want to be part of that building program."

Blair was involved with a plan to start a new Oshawa Generals franchise in a new arena in Oshawa, Ontario. Despite the Bruins already having a junior hockey franchise, the Niagara Falls Flyers, Blair convinced the Bruins to own another. He arranged a deal whereby the Bruins owned 51% of the franchise. But Orr would have to play for Oshawa. When Orr was fourteen, Blair convinced the Orr family to allow Bobby to attend the Flyers' tryout camp. When camp ended and it came time to sign with the Bruins, a meeting with Bruins' owner Weston Adams went sour and Orr headed back to Parry Sound. Blair was able to smooth over the situation and convince Arva Bobby was old enough to leave home. To get the Orrs' signatures on a "C" Form, committing Bobby to the Bruins at age eighteen, Blair agreed to have Bobby stay in Parry Sound for his schooling, skipping Generals' practices and only driving south to play games on weekends, a three-hour trip one way. The bonus for signing was CA$10,000 (CA$83,899 in 2018 dollars), a new car and the Bruins would pay to stucco the family home.

Eagleson was determined to get Orr a top salary. When Hap Emms, the general manager of the Bruins offered a US$5,000 (US$39,400 in 2019 dollars) signing bonus and US$7,000 and US$8,000 (US$55,160 and US$61,341 in 2019 dollars) for his first two years in the league, Eagleson countered with US$100,000 (US$788,000 in 2019 dollars) for the two years. Orr would refuse to play with the Bruins and played for Canada's national team instead, like Carl Brewer. Orr wanted desperately to play in the NHL, but he went along with Eagleson's strategy and was willing to play for the nationals. The Bruins and Orr agreed on a US$25,000 signing bonus (US$197,000 in 2019 dollars), and a salary "less than $100,000" for the two years, a figure kept secret. Speculation has ranged on an annual salary of US$25,000 to US$40,000 (US$197,000 to US$354,600 in 2019 dollars) at a time when the typical maximum rookie salary was US$9,000. (US$63,040 in 2019 dollars) The official signing ceremony was done on Emms' boat, the Barbara Lynn, where Eagleson and Emms had conferred during negotiations.

Orr's contract with Chicago, five years in length, was for US$3 million, (US$13,478,947 in 2019 dollars), to be paid over 30 years. Spreading out the payments in this way was done to minimize taxes. While a player, he never cashed a Chicago paycheque, stating that he was paid to play hockey and would not accept a salary if he was not playing.

Orr publicly supported incumbent Donald Trump in the 2020 United States presidential election.