Alan Eagleson was a lawyer, player agent, founder of the NHL Players’ Association, father of international hockey, and a convicted criminal. His story is filled with bittersweet irony. Read more on torontoski.
Accusations of Fraud Against Alan Eagleson
Eagleson grew up in Toronto’s western suburbs, the son of a factory worker determined to achieve something significant in his life. And Alan did just that—he became arguably the most influential person in hockey. However, he later fell from grace. Once hailed as the great emancipator of NHL players, Eagleson ended up branded as a traitor and a fraudster. This culminated in January 1998, when he was sentenced to 18 months at the Mimico Correctional Centre. The reputation and influence he had painstakingly built were utterly destroyed.
History will undoubtedly remember Eagleson for the final chapter of his hockey career: a plea deal on three counts of fraud in a Boston courtroom, followed by another three counts of fraud in a Toronto courtroom. If that is his legacy, so be it. However, history cannot ignore Eagleson’s profound impact on hockey business. Some of his influence was positive, while some was not, but Eagleson was undeniably a driving force in the sport and the business of hockey for over 25 years.
Influential Friendships and the Fight for Hockey Players’ Rights
In 1966, a young Toronto lawyer named Alan Eagleson was hired by budding superstar Bobby Orr to negotiate his contract with the Boston Bruins. Ironically, the eventual breakdown of Eagleson’s relationship with Orr years later would significantly contribute to Eagleson’s downfall.
Eagleson’s journey into the NHL began in the early 1960s through his friendship with Bob Pulford, then a centre for the Toronto Maple Leafs, cultivated via their mutual involvement in lacrosse. Through Pulford, Eagleson met many Leafs greats, including Bobby Baun, Terry Sawchuk, and Carl Brewer. Eagleson helped these players negotiate contracts and investments. However, it was his association with Orr that launched Eagleson’s meteoric rise to fame and fortune. In the summer of 1966, the Bruins offered Orr, an 18-year-old defensive prodigy from the Oshawa Generals, a two-year contract worth approximately $20,000, including bonuses. When Eagleson was done negotiating, the deal had ballooned to $70,000, making it the largest rookie contract ever. Orr was stunned.
That same year, Eagleson was called upon by the Springfield Indians of the American Hockey League to represent them against their owner, Eddie Shore, a hockey legend turned tyrant. The players demanded improved working conditions and enlisted Eagleson, who threatened legal action and negotiated a settlement. During this time, Eagleson met with Orr and some Bruins teammates, who suggested he consider forming a union. Eagleson gathered opinions from players across the league, and within months, 110 players had signed in support of a union, with another 10 giving verbal approval.
Chicago Blackhawks superstar Bobby Hull remarked, “Eagleson has done more for hockey in two years than anyone else has in 20.”
The Push for Recognition of the Players’ Association and Salary Increases
In May 1967, a confident 34-year-old Eagleson informed NHL President Clarence Campbell that he would attend the league’s annual meeting in Montreal to seek recognition of the NHL Players’ Association. Ten years earlier, New York lawyer Milton Mound had tried to establish a players’ union but failed, with supporters such as former Detroit Red Wings star Ted Lindsay facing repercussions.
Eagleson, however, was unstoppable. Within two weeks, on June 7, 1967, he convinced league executives to recognize the NHLPA just 15 minutes after presenting the idea. Trent Frayne, a journalist, described Eagleson as the most influential figure in Canadian sports since Conn Smythe paid off the mortgage for Maple Leaf Gardens in 1967.
Eagleson quickly secured several victories for players, including raising the minimum salary from $7,500 to $10,000, improving medical benefits, and introducing a better pension plan. For years, players had been underpaid, undervalued by owners, and left unprotected after retirement. Eagleson changed much of this, laying the groundwork for the prosperity players enjoy today.
Outside the NHLPA, Eagleson expanded his services, becoming the first prominent agent in hockey. His efforts soon ensured that every player had representation during contract negotiations. Within a few years, Eagleson was a force to be reckoned with, building an empire as both an agent and NHLPA executive director.
The Progressive Conservative Party and a Series That Changed Hockey History
Beyond hockey, Eagleson ventured into politics, serving as a Member of Ontario’s Legislative Assembly with the Progressive Conservative Party in 1963. After losing his seat in 1968, he became the party’s president, holding the position for eight years. Despite his political involvement, Eagleson maintained his deep connections to hockey, balancing multiple roles with apparent ease.
In 1972, Eagleson played a key role in organizing the historic Summit Series between NHL players from Canada and the Soviet Union, a groundbreaking moment in international hockey. The eight-game series—held in Montreal, Toronto, Winnipeg, Vancouver, and Moscow—was a chance for Canada to prove its hockey supremacy. After years of sending amateur teams to world championships and the Olympics, Canada was determined to assert its dominance with professional NHL players.
This series forever changed the perception of hockey on a global scale.
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