Bobby Orr’s Untold Story of Leaving the Bruins: Was His Agent Betraying Him?
Bobby Orr, the flying defenseman who revolutionised hockey, is considered a legend by the majority of hockey enthusiasts. He still gives people chills for his famous overtime goal in the 1970 Stanley Cup Final. However, many people are unaware of the story of trust, treachery, and grief that lies beneath his legendary career.
The Legend’s Ascent
Not only was Bobby Orr talented, but he was a trailblazer. He led the Bruins to two Stanley Cups and won eight straight Norris Trophies as a defenseman who could skate, pass, and score like a forward. Boston became his second home, and his fans loved him.
Then the shock hit. Bobby Orr left the Bruins in 1976.
Why would a player who is so adored by the club and city leave?
The answer is more complex than contracts or injuries alone.
Presenting Alan Eagleson, Orr’s agent and the person he most trusted
Alan Eagleson, Orr’s agent, was like family, not just a negotiator. Orr put his future, his money, and his career in his hands.
However, that confidence would turn out to be a disastrous error.
Eagleson informed Orr that Boston was only making a nominal offer when his contract with the Bruins expired. Rather, he convinced Orr that signing with the Chicago Blackhawks was the wisest course of action both financially and professionally.
Orr would not learn until long later that the Bruins had actually promised him a 25% ownership part in the team in exchange for his continued loyalty.
Eagleson didn’t tell him.
Why? Because Bobby’s best interests weren’t one of Eagleson’s, who had his own interests and covert agreements.
A Career Cut Short, a Legend Betrayed
Orr’s knee issues worsened after he signed with Chicago. He only played 26 games in three years and retired far too early at the age of 30. The Chicago chapter was emotionally and physically taxing.
When the truth came out about Eagleson’s lies, Orr was devastated. Not only had he lost his chance to be a lifelong Bruin, but his finances were in shambles. Eagleson had mishandled and embezzled money, leaving Orr nearly broke.
In later interviews, Orr admitted:
“Had I known what the Bruins were offering, I never would have left.”
A Painful Lesson, A Lasting Legacy
Today, Bobby Orr is still one of hockey’s most respected icons. He went on to rebuild his life, help young players avoid similar mistakes, and even testified against Eagleson — who was later convicted and disbarred.
Orr’s story is a powerful reminder: even the greatest legends can be betrayed — but true character is how you respond.
Do you think Bobby Orr should’ve spent his entire career in Boston?
Share your comments and tag a Bruins fan who needs to see this.