Alan Eagleson Robert Alan Eagleson ( born April 24 , 1933 ) is a disbarred Canadian lawyer , convicted felon in two countries , former politician , hockey agent and promoter . Clients that he represented included superstars Bobby Orr and Darryl Sittler , and he was the first executive director of the NHL Players Association ( NHLPA ) , which was initially lauded for improving the bargaining power of NHL players . He is also well known for giving the opportunity for professional players to compete in international hockey , by promoting the 1972 Summit Series between Canada and the Soviet Union , and the Canada Cup ( now the World Cup of Hockey ) . However , Eagleson was convicted of fraud and embezzlement and briefly imprisoned , after it was revealed that he had abused his position for many years by defrauding his clients and skimming money from tournaments . The Blue and White Group . Eagleson graduated in law from the University of Toronto and soon became a prominent lawyer in Toronto . He first became involved with hockey as an advisor to Bob Pulford , a player with the Toronto Maple Leafs . It was quickly realized that any attempt to create a union would be easier to achieve with Leafs ' players as his base of power . That led to other members of the Leafs becoming clients , most notably defenceman Carl Brewer , who hired Eagleson as his agent . Eagleson would form the Blue and White Group , a group of friends he had known from the Maple Leafs , including Brewer , Pulford , Bobby Baun and Billy Harris , along with a car dealer , a jeweller , and three other lawyers . Eagleson ' s motive was to educate these players about investments , and use their funds more intelligently . Pulford , Brewer and Harris would earn university degrees after their playing careers . Two members of the Blue and White Group , Pulford and Baun , would be the first two presidents of the NHLPA . The Leafs ' acquisition of Andy Bathgate would prove advantageous to Eagleson . A friendship was forged in Toronto which would follow Bathgate to Detroit , where Eagleson would start to talk to Red Wings players about the concept of a union . A hockey power . Three events would occur that would help Eagleson form the NHLPA . The first event would be the insistence that Eagleson would negotiate Bobby Orr ' s first pro contract with the Boston Bruins . This would lead to the beginnings of " agents " in hockey . Secondly , Carl Brewer fought to have his amateur status reinstated . Lastly , Eagleson would be involved in representing the Springfield Indians during their negotiations with owner Eddie Shore over players rights . These events would solidify Eagleson ' s reputation , and he would become the catalyst for the NHLPA . When the NHLPA was formed in 1967 , Eagleson was appointed its first executive director , a position he held for 25 years . By 1979 , Eagleson represented more than a dozen players of the Toronto Maple Leafs , including Darryl Sittler and his best friend and linemate , Lanny McDonald . Eagleson had a strained relationship with Leafs owner Harold Ballard and general manager Punch Imlach . Imlach believed Sittler had too much influence on the team and tried to undermine his authority with the players . When Sittler and goaltender Mike Palmateer agreed to appear on the TV show " Showdown " , as negotiated by the NHLPA , Imlach went to court to try to get injunction to stop them . When Imlach said that he was open to offers for Sittler from other teams , Eagleson said it would cost $ 500 , 000 to get Sittler to waive the no - trade clause in his contract . So , instead of trading Sittler , Imlach sent McDonald to the woeful Colorado Rockies on December 29 , 1979 . In response , Sittler ripped the captain ' s " C " off his sweater , later commenting that a captain had to be the go - between with players and management , and he no longer had any communication with management . Ballard would liken Sittler ' s actions to burning the Canadian flag . Within a decade , Eagleson was one of the most powerful men in hockey , and by some accounts , the most powerful man in the sport . He was even elected to the Hockey Hall of Fame in 1989 as a builder - - the only known instance where a union official has been elected to the hall of fame in a major team sport . That same year , he was named an Officer of the Order of Canada for his work in promoting the sport . Over the years , Eagleson developed a very close relationship with league president John Ziegler . For all intents and purposes , the NHL of the 1980s was ruled by a triumvirate of Ziegler , Eagleson and Chicago Blackhawks owner Bill Wirtz . International Hockey . Eagleson was also active in promoting the sport , helping to organize the historic 1972 Summit Series — the first time Canadian and Soviet pros had ever competed against each other on the ice . Notably , Eagleson was responsible for the decision to exclude many WHA stars from the Summit Series , including Bobby Hull , Gerry Cheevers and Derek Sanderson , as they had defected from NHL teams . Four years later , Eagleson organized the first Canada Cup , which included WHA players . During one of the Summit Series games in Moscow , Eagleson garnered international attention by attempting to confront off - ice officials after the goal judge had failed to light the goal lamp when a Canadian player scored , at which point he was seized by soldiers of the Red Army . The Canadian players and the few Canadian fans rallied to his defence to prevent him from being arrested , providing one of the most memorable off - ice moments of the series . As they walked back across the ice Eagleson allegedly extended his middle finger to the Russian crowd . Political career . Eagleson was also active in politics for many years . In the 1963 federal election , he ran unsuccessfully for a seat in the Canadian House of Commons for the Progressive Conservative Party of Canada in the Toronto riding of York West . He was defeated by hockey player Red Kelly who ran for the Liberal Party of Canada . Later that year , he was elected to the Ontario Legislative Assembly as the Progressive Conservative Member of Provincial Parliament for the Toronto riding of Lakeshore , serving there until 1967 . He was a major PC fundraiser and , in the late 1960s , president of the Progressive Conservative Party of Ontario . He was a member of the Big Blue Machine that dominated Ontario politics for much of the 1970s and 1980s . At one point , his name was considered as a potential candidate for prime minister of Canada . Controversy . As Eagleson ' s power grew , concern was raised about his multiple roles as union chief , player agent and hockey promoter . Suspicions also rose that he was reaping a substantial windfall from the Canada Cup and other arrangements unknown to the players . However , until 1989 he was considered a national hero in Canada and an icon in the NHL . In addition , many local Canadian journalists owed favours or access to Eagleson . In 1989 , however , player agents Ritch Winter and Ron Salcer teamed up with former National Football League union official Ed Garvey to author a devastating review of the NHLPA ' s operations . Winter and Salcer had been critical of Eagleson ' s stewardship for many years , and felt he wasn ' t giving them the support they needed to adequately represent their clients . The report , presented at a union meeting in West Palm Beach , revealed that Eagleson ' s travel expenses were not subject to any form of review by the union . Winter and Salcer also charged that Eagleson was skimming off money from advertising on the dasher boards , and had lent pension money to friends . Eagleson was able to weather this storm because the union ' s executive committee was stacked with longtime cronies . However , he was forced to announce that he would be stepping down as executive director in 1992 . Conway investigates . In 1990 , Russ Conway , sports editor of The Eagle - Tribune , began an investigation of Eagleson ' s performance in office . Conway had heard rumours for some time that something was seriously amiss about the inner workings of the NHL — specifically serious discrepancies in pension payments . Despite the devastating 1989 report by Winter and Salcer , most Canadian journalists refused to look into the rumours . Over the course of a year , Conway interviewed more than 200 NHL personalities , including former and active players and NHL officials . In September 1991 , he published the first of many installments in a series called " Cracking the Ice : Intrigue and Conflict in the World of Big - Time Hockey . " The series revealed evidence that Eagleson had engaged in a staggering litany of unethical and criminal conduct over many years . Conway ' s writings alleged that Eagleson had embezzled player pension funds for many years , principally from the 1972 Summit Series . He was also accused of colluding with teams whose management he favoured , such as the Chicago Blackhawks , to hold down salaries , even if it meant working contrary to the interests of his clients . For example , after Orr ' s contract with Boston ran out , Eagleson told Bobby Orr that the Blackhawks had a deal on the table that Orr couldn ' t refuse . It later emerged that the Bruins offered Orr one of the most lucrative contracts in sports history , including an 18 percent stake in the team ; however , Eagleson falsely claimed the Blackhawks had a better offer . Wirtz was never charged with wrongdoing , largely because the Bruins ' offer was widely known in league circles , and even reported in the " Toronto Star " . No other NHL owner was ever charged in the affair . Orr was once one of Eagleson ' s strongest supporters , but later denounced him after suspecting that he was being cheated . Orr , whose career ended in 1978 because of serious knee injuries , learned from an independent accountant that he was almost bankrupt , despite having supposedly earned high salaries while being represented by Eagleson . However , the series ' most shocking revelation concerned Eagleson ' s actions regarding disability claims by former players . Eagleson was accused of taking large payments from insurance claims before the players filing them received their share , telling the players that he earned the " fee " while fighting against the insurance companies to get the claims paid . In fact , many players later learned that the insurance companies had already agreed to pay the claims and there was no " fight " . In other cases where a " fight " with the insurance companies was required , several players ran into bureaucratic dead ends and no support from Eagleson while they tried to move forward on insurance and pension claims to support their families . One of these cases that moved Conway particularly was that of second - line defenceman Ed Kea , who suffered a devastating head injury that required major brain surgery . This not only ended Kea ' s playing days but also jeopardized his post - hockey career and finances , yet Eagleson had " thrown the case out " saying that Kea was no longer worth representing , not even having the " decency " to visit Kea ' s family . Conway later turned his series into the basis of a book , " Game Misconduct : Alan Eagleson and the Corruption of Hockey . " Conway published several other stories over the next nine years about Eagleson ' s crimes . For instance , he ' d been reimbursed more than $ 62 , 000 for personal expenses from 1987 to 1989 . He also revealed that the NHLPA had unknowingly footed the bill for expensive clothing , theater tickets and a luxury apartment in London . Many players had been led to believe that they were playing in the Canada Cup for free because all the money was going to their pensions . Conway worked very closely with Carl Brewer , one of Eagleson ' s early clients . Brewer had by this time become the leader of a group of former players who felt Eagleson had lied to them . Brewer ' s longtime companion , Susan Foster , provided a large amount of material to Conway . Although Eagleson had been based in Toronto , most Canadian media organizations had avoided detailed investigation of his dealings until Conway ' s material was published . That changed when " The Globe and Mail " began its own examination of Eagleson ' s career in early 1993 , and published a series of stories with further revelations . Two Globe sports writers , William Houston and David Shoalts , expanded that material , Conway ' s work , and the latest developments into their own book , entitled " Eagleson : The Fall of a Hockey Czar " , which was published later in 1993 . Criminal charges and extradition . In 1996 , after a politically delayed three - year investigation , the Royal Canadian Mounted Police finally was forced , by Conway ' s publications , to charge Eagleson with eight counts of fraud and theft . He ' d already been charged by the FBI with 34 counts of racketeering , obstruction of justice , embezzlement and fraud in the United States in 1994 . However , he still had enough political clout from his days as an MPP and a power broker with the Tories that he was able to fight off extradition to the United States until 1997 . Some of Eagleson ' s former clients remarked that had it not been for the US justice system , Eagleson would have never been charged . After being arrested , one FBI agent said that Eagleson " just didn ' t get it " that he was guilty , as the former sports agent was tinkering with police equipment while being booked . On January 6 1998 , Eagleson pleaded guilty to three counts of mail fraud in Boston , and was fined $ 700 , 000 . Later that year , he pleaded guilty in Toronto to three more counts of fraud and embezzling hundreds of thousands of dollars of Canada Cup proceeds in 1984 , 1987 and 1991 . He was sentenced to 18 months in prison , of which he served six months at the Mimico Correctional Centre in Toronto . The conviction resulted in his automatic disbarment from the practice of law by the Law Society of Upper Canada , which regulates the profession in Ontario . Since being released , he has largely remained out of the limelight , although he was interviewed on television after Canada ' s loss to Russia in the 2006 Winter Olympic Games in Turin , Italy . Removal of honours . Soon after his guilty plea , Eagleson was removed from the Order of Canada , though he continued to wear his lapel pin during the court proceedings prior to his sentence . Eagleson also resigned from the Hockey Hall of Fame after the Hall ' s board informally voted to expel him ( a formal vote , which was almost certain to pass , was due within a few weeks ) . The Hall had tried to stay out of the controversy , but was forced to act after 19 Hall of Fame players — including Orr , Bathgate , Hull , Gordie Howe , Jean Beliveau , Mike Bossy , Johnny Bucyk , Ted Lindsay , Henri Richard , Brad Park , Johnny Bower and Dickie Moore - - threatened to resign from the Hall if Eagleson was allowed to remain . He became the first member of a sports hall of fame in North America to resign . Legacy . Defenders of Eagleson pointed out that during his tenure as executive director of the NHLPA , both salaries and pension benefits increased exponentially , offering real security to players that had not existed prior to that time . The earlier NHLPA only lasted a year , as owners broke the union in 1957 by trading players involved with the organization or sending them to the minor leagues , which led out - of - court settlement over several players ' issues in return for the disbanding of the union . There was some controversy that Eagleson ' s directives ( aside from instances where he colluded with favored owners to hold down wages ) contributed , as well as the formation of the rival WHA , to rapidly increasing player salaries , something especially advocated by his successor Bob Goodenow . During the criminal proceedings against him , several players whom he had defrauded were amongst his biggest supporters . Many of his most ardent supporters during and after his trial were famous and prominent clients who had benefited from his activities , including high profile hockey personalities such as Bobby Clarke , Bob Gainey , and Marcel Dionne , and former Prime Minister John Turner . Moreover , prior to Eagleson ' s involvement , North American professional players had never participated in international hockey , an involvement that later grew into involvement in the World Hockey Championship , the World Cup of Hockey , and the Winter Olympic Games . Eagleson ' s maximum official salary as executive director of NHLPA was one - tenth of that of his successor , Bob Goodenow . While Eagleson ' s close relationship with Ziegler and Chicago Blackhawks owner Bill Wirtz led to them forming a cooperative triumvirate , this ended immediately with Goodenow ' s accession to the NHLPA . Just two months after being appointed head of the union , Goodenow led the players out on a 10 - day strike on the eve of the Stanley Cup playoffs , which fundamentally altered the relationship between the league and its players . Goodenow called the strike a " major moment " , stating " I don ' t think the owners took the players seriously and it wasn ' t until the stike that they understood the players were serious . " Ziegler was ousted as NHL president following the season , and Gil Stein was named to succeed him on an interim basis until Gary Bettman was chosen . There were further work stoppages in 1994 - 95 and 2004 - 05 .