Bobby Orr: The Defenceman Rests

Photography: Chris Chapman

… but not on his laurels. In his long-awaited autobiography, Bobby Orr reveals how he overcame financial ruin and is now living the happiest chapter of his life

Photography Chris Chapman

Everywhere you go in Parry Sound, Ont., a small Georgian Bay town two hours north of Toronto, you’re bombarded with reminders that it’s the birthplace of the greatest hockey player ever. Driving past the cottage townships, you exit the highway just after the sign proudly declaring “Home of Bobby Orr.” Stay on the main drag, cross the bridge and turn right, you’ll hit the Bobby Orr Community Centre. Turn left on Bay Street toward the marina, and you’ll reach the Bobby Orr Hall of Fame.

But the heart and soul of Bobby Orr country is really found on a little inlet that branches off the Seguin River. In the dead of winter, it freezes just right, forming a perfect sheet of ice. This was young Bobby’s rink of dreams, where he developed his love, passion and flair for the game.

A frozen river, pond or outdoor rink, it was here that the spirit of the sport once flourished: outside against elements, 10 skaters a side, toques for helmets, boots to mark goal posts, grab the puck and go – the sport in its purest form, untainted by referees, coaches or parents.

But that nostalgic idyll has long since vanished, melted away like the ice on the Seguin that day I visited Parry Sound to interview the former Boston Bruins great about his recently released autobiography, Orr: My Story. I not only want him to reminisce about his starry career but to also open up about the bitter end-of-career financial woes, an appalling episode brought on when his business partner and close friend betrayed him.

The problem is that Robert Gordon Orr is famously – and understandably – reticent about discussing the embarassing events that led to his bankruptcy. Modest in the old sense of the word, he’s shy in front of crowds and cameras, hastily deflects praise and would rather talk about just about anything – his parents, family, coaches, teammates, his best friend Don Cherry, the recent inductees to his Hall of Fame, rule changes that are hurting hockey – than expound on his personal life.
“Talking about myself is not my thing,” he says before we even sit down. It’s not a promising start and might explain why it’s taken him so long to release his autobiography. Plus, he’s already taped a lengthy television interview with Peter Mansbridge and seems wary of the prospect of another hour talking about himself, doubly irritating because he knows he’ll have to recall the painful past.

But Orr, obligingly, has agreed to do the PR thing. Today, clad in a black-and-gold Boston Bruins’ windbreaker with athletic shorts, he looks as fit as when he played. Turning 66 this month, and still very much a Canadian icon, he retains a stocky, athletic build with muscular forearms. And, along with the friendly blue eyes, prominent nose, ample jaw and lopsided grin, there’s a lot left of that boyish visage that adorned magazines, hockey cards, posters and lunchboxes of countless Canadian kids four decades ago.

The rise and fall and subsequent re-making of the financial house of Orr began in 1960, when reports of a defenceman with otherworldly talent began circulating through the hockey world. With professional teams salivating to sign the burgeoning star, Wren Blair, a scout for the Boston Bruins befriended Bobby’s parents, Doug and Arva, and began the process of signing their son to his first professional contract. The Orrs were by no means a rich family. Both parents held down multiple jobs – Doug drove taxi and packed dynamite at the local CIL plant – and any money their son could earn would come in handy. In 1962, the two sides came to terms: in return for their 14-year-old signing to play with the Oshawa Generals (a junior team affiliated with the Bruins), the family would receive $1,000 (“a considerable sum in 1962”), his dad would get a used car and the family’s ramshackle old house would receive a much-needed stucco job. Oh, and the Bruins generously agreed to throw in a new suit for Bobby. “It was charcoal,” he remembers. “And when I finally slipped it on, I felt like the coolest dude in town.”

Looking back, Orr laughs at the absurdity of those terms. “There simply wasn’t much money being thrown around,” he says in typical understatement. Today, a rookie like Orr would receive a minimum salary of $925,000.

But bigger paydays and nattier suits would soon follow. In 1966, Orr signed his first pro contract with Boston, a two-year deal paying him $35,000, good money for a hockey player but paling in comparison to the $400,000 deal Joe Namath had signed to play for the New York Jets of the American Football League.

In his first NHL game, Orr picked up an assist as well as a crunching elbow from his idol, Gordie Howe. “I was watching a pretty pass I just made and whack, Gordie nailed me. Hit me pretty good,” he says, maintaining that Howe’s rough treatment of the precocious rookie was entirely justifiable. That lesson learned, Orr embarked on a 10-year run where he dominated the sport like no one before or since. He brought fans to their feet and goalies to their knees, praying they wouldn’t be made to look silly by a ridiculous deke or no-look pass. At a time when most blueliners were anchored in their own zone, Orr forced the puck up the ice, using a combination of blinding speed and deft moves first learned on the frozen river. Legendary Montreal sports writer Red Fisher, who covered all the greats – Richard, Gretzky, Lemieux and Crosby – feels Orr stands alone. “He pulled me out of my seat more than any player I ever watched. As far as I’m concerned, Orr is the best I’ve ever seen and he always will be.” Along with Phil Esposito, Derek Sanderson and a colourful collection of carousing brawlers, the Big Bad Bruins ruled the ice, winning the Stanley Cup in 1969-70 (clinched by Orr’s famous flying goal) and again in 1971-72.

Away from the ice, life was going well too. In 1973 he quietly married Florida-born Margaret (Peggy) Wood, a partnership that lasts to this day, producing two sons, Darren and Brent. But there were growing concerns that his fragile knees were forcing the star to miss an alarming number of games. Orr’s all-out style of play made huge demands on his body, and his refusal to dial back the intensity didn’t help. “I played a contact game. And when you play a contact game you get hit a lot.”

As the knee operations mounted (14, by Orr’s count), he wouldn’t change his game. “I thought I was indestructible,” explains Orr. “I thought I would play forever.” It’s the familiar lament of star athletes who cannot see the end coming until a sudden injury brings it a lot closer. But at the time he wasn’t worried, as a massive celebrity, he was having the time of his life, winning Cups, partying with teammates and making big money. The future seemed secure, except that it rested in the hands of a confident, aggressive and, as it turned out, unscrupulous Toronto lawyer name Alan Eagleson.

When Eagleson’s name comes up today, Orr shakes his head – he still finds it intensely hard to say the man’s name. In fact, Orr wanted to avoid the Eagleson era altogether in his book but was convinced otherwise. Eagleson established contact with the Orr family back in 1964, at 16-year-old Bobby’s end-of-season baseball banquet. Ever the smooth talker, he convinced Doug and Arva that their budding superstar needed a player agent to handle his financial affairs and promised he could make their son a lot of money. “We … did not have a lot of experience with these types of matters,” Orr laments, explaining why the family took the fateful step of agreeing to the partnership.

At first, Eagleson fulfilled his role admirably, making Orr the highest paid hockey player of his era. In 1968, he negotiated a three-year deal for $250,000 (worth about $1.6 million in today’s money.) It was a huge amount for that time – Gordie Howe, then the game’s greatest star, was still earning in the vicinity of $45,000 a year – but nothing compared to the earnings
of today’s superstars: like Sidney Crosby, who hauls in $8.7 million a year. Eagleson also set up a dodgy scheme called Bobby Orr Enterprises Ltd, where Orr plowed in his earnings and investment assets (real estate, men’s clothing store, a hockey camp) and from which he drew a annual salary. With bravado to burn, Eagleson often loudly boasted that his client was “fixed for life.”

The opposite was in fact true. Eagleson seized financial control of a growing empire and began making questionable decisions, mainly because Orr seemed disinterested in tracking his assets. Eagleson once said of his client: “He is entirely unmotivated by any personal desire for money.”

That’s not how Orr remembers it. “I trusted him,” he says. “Many people tried to tell me that he was no good for me but I ignored them because … because he was like a brother.” As the agent used his guru status to take over personal and financial decisions, Orr became frustrated. “I couldn’t find a way to get myself out of his clutches.”

It all started unravelling in 1975 during a final contract negotiation with the Bruins. Eagleson convinced his client to shun Boston’s offer and instead sign a six-year deal worth $500,000 with the Chicago Blackhawks, no doubt spurred by the close personal relationship he enjoyed with owner Bill Wirtz. Worse yet, Eagleson neglected to inform Orr of a lucrative counter-offer from the Bruins, which included an unheard of 18 per cent ownership stake in the team – a plum that would be worth about $100 million today. Orr claims he would have jumped at the Boston offer had Eagleson informed him of it. “Even someone with my limited financial skills would have known which offer would have been most lucrative in the long haul.” Instead, he packed up his skates and said bye-bye to Beantown.

By the time he reached Chicago, his shredded knees could no longer take the strain of playing and, before one last hurrah at the 1976 Canada Cup, where he heroically played through pain and was named MVP, his career came to a grinding halt after only 26 games over his final three years. At a tearful press conference in 1978, the greatest hockey player ever announced his retirement.
His playing days done, Orr had another shock coming. In the summer of 1979, U.S. authorities gave notice that Orr’s corporation was on the hook for massive back taxes. When the IRS demanded he pay up, the balance sheet showed his assets amounted to $456,604 with liabilities of $469,546. In effect, he was bankrupt. “Where all the money went, I will never know,” says Orr. Eagleson, defending himself in his self-serving book Powerplay: The Memoirs of a Hockey Czar, suggested that “[Orr] took all the money coming to him, and more, and spent it all. Years later, he’s still trying to make out that the reckless things he did with his money were my fault.”

Eagleson’s blustery defence holds little water, especially in light of his growing legal troubles. After years of fending off allegations that he was defrauding players, in 1994, he was charged by the FBI with 34 counts of racketeering, obstruction of justice, embezzlement and fraud. In 1998 he pleaded guilty in Canada to three more counts of fraud and embezzling. He was sentenced to 18 months in prison.

That came too late for Orr. Left virtually crippled and broke, he was about to join the ranks of highly paid athletes who retired penniless. “I had a young family, I was moving back to Boston and I had to buy a home. Most of all, I needed work.” Lacking the will – or money – to go after Eagleson in court, he set to rebuilding his stake. “I drew on the lessons I learned as a kid: being disciplined, making sacrifices and being responsible.”

The fact that Orr managed to restore his battered financial house rates as an accomplishment on par with anything he did on the ice. Taking stock with Peggy, he discovered all he had left was the star power behind his name. Fortunately, many Canadian- and Boston-based companies were eager to have him pitch banks, cars, cereal, credit cards, etc. Gradually, he rebuilt his crippled finances, became a player agent in the mid-’90s and completed the comeback in 2002, when he formed Orr Hockey Group, an agency that represents hockey players from Ontario and northeastern U.S. Working with son Darren, his client list includes some of the game’s bright stars and, according to, it’s now the fourth most valuable agency, managing more than $400 million dollars in player contracts.

The first advice he bestows on his young charges is the importance of minding their finances. “My big mistake was not paying attention. It was my money. But I trusted Eagleson and believed in him and just let him run things. I don’t care how close you are to someone – money is a funny thing and it makes people do funny things.”
The news is equally good on the health front. Thanks to double knee replacements, he walks, bikes and can golf 18 without using a cart (no surprise: he’s hit a hole-in-one). And remarkably, he’s skating again, recently taking to the ice before the outdoor game in Boston.

These days, besides his voluminous charity work, he’s constantly on the road, signing up young players. Dividing down time between Cape Cod and Florida, he’s always happiest back in Canada, where he’s still a citizen. And he follows the game closely – anytime the Bruins are in the playoffs, TV cameras will capture Orr in the stands, once again drawing huge ovations from the Boston faithful.

“I’m a lucky guy,” he tells me as he wraps up the interview, off to make an appearance at a local baseball tournament. “Business is great. I play a little golf and do a little fishing. My kids are set up. I’m spending time with Peggy in Florida and Cape Cod. Playing with my two grandkids is heaven … I’m really at peace with my life.”

As I pack up to clear out, I notice he’s looking rather pleased with himself. “Even after talking about Eagleson all morning, I’m still in a good mood,” he laughs, shaking hands. “Geez, life must be good.”

Zoomer magazine, March 2014.