Bobby Orr

Orr played in Boston (or "Orr Country," as a popular bumper sticker of the time dubbed it) for six more seasons after that first Stanley Cup. He helped bring the Stanley Cup back to the city in 1972, again scoring the winning goal, and he remained a favorite of Bruins fans.

A bizarre twist marred the end of Orr's hockey career for many Bostonians. In 1976 Orr's long-time agent, Alan Eagleson, was negotiating a new contract for him. Orr wanted to remain with the Bruins, and the Bruins desperately wanted to keep him, offering him an 18.5% ownership stake in the team, worth millions, if he would stay. However, Eagleson had unethical ties with Chicago Blackhawks owner Bill Wirtz, who also wanted Orr. Eagleson concealed Boston's offer from Orr and convinced him that Boston didn't want him to stay. Orr signed the deal with Chicago.

Orr was at that time struggling to play at all. He had suffered from knee problems ever since colliding with a teammate in a charity-benefit game in 1967. By 1976, he had already had multiple operations on his left knee, but in the days before artificial knees there was little that the doctors could do. There was nearly no cartilage remaining in the joint, and the sensation of bone rubbing against bone was excruciatingly painful. After playing only twenty-six games in just over two seasons with Chicago, Orr announced his retirement in a tearful news conference on November 8, 1978. Later that season, he received an eleven-minute standing ovation from the crowd in Boston when his #4 was retired. That same year, 1979, Orr became the youngest player ever to enter the Hockey Hall of Fame.

Orr's troubles with Eagleson did not end with his retirement. Eagleson, who had been representing Orr before he signed his first contract with the Bruins, had mismanaged Orr's finances in a way that left him in deep trouble with both the Canadian and the American tax agencies. Between back taxes and legal bills, Orr was essentially bankrupt by 1980. The full extent of Eagleson's crimes, however, would not become apparent for many more years. In 1992, Eagleson was indicted in the United States on thirty-two counts of racketeering, fraud, and embezzlement related to the time he spent heading the NHL players' league. He eventually served an eighteen month sentence. After Eagleson's conviction, Orr was one of eighteen members of the Hall of Fame who threatened to quit the hall if Eagleson, also in the Hall of Fame, was not removed. (He was.)