Bobby Orr - Post-hockey Career

Post-hockey Career

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$1,462,138 in 2012 dollars) and his tax, legal and accounting bills totalled US$469,546 (US$1,503,581 in 2012 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 of Orr's assets for $US620,000 (US$1,748,821 in 2012 dollars), including his Orr–Walton Hockey Camp, which paid off US$450,000 (US$1,269,305 in 2012 dollars) of Orr's bank loans.

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$1,050,050 in 2012 dollars), one-third of the money owed him. Of this, US$200,000 (US$466,689 in 2012 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 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 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 law suit 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 law suit 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 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.

The group represents such players as Jason Spezza, Eric Staal, Jordan Staal, Marc Staal, Nathan Horton, Jeff Carter, Steve Downie, Anthony Stewart, Tomas Kaberle, Taylor Hall and Colton Orr (no relation). Spezza, asked to comment on the experience of having Orr as an agent, replied: "I don't think I have a true feeling for how great he is. I have so much respect for him. I watch him on tapes and it's just ridiculous how good he was compared to the guys he was playing against. He's a great guy and you don't even know it's Bobby Orr, the way he talks to you."

For a number of years, Orr has coached a team of top Canadian Hockey League junior players against a similar team coached by Don Cherry in the annual CHL Top Prospects Game. Cherry, briefly his former coach in Boston, considers Orr the greatest hockey player who ever lived, noting that Orr was a complete all-around player who could skate, score, fight, and defend. As of 2010, Orr's teams have won most of the games, winning seven of the eleven times Orr has coached against Cherry. Orr's participation was criticized as a conflict-of-interest while he was a player's agent and he stopped coaching in the series. Organizers of the series convinced Orr to return to coaching in the series. He stepped down again before the 2011 game for the birth of his second grand-child. One of the teams remained named 'Team Orr.'