During his first season in Junior, the Oshawa Generals played an exhibition game in Parry Sound against the Junior B Shamrocks, who then had Bobby's older brother Ronnie, as part of their lineup.

During the game, a huge brawl broke out, players squared off around the ice and the Orr brothers found themselves standing face to face.

They did what hockey players, brothers or not, are supposed to do in such circumstances.

They fought.

And Bobby dropped brother Ron flat on his back.

On December 22, 1966, Bobby Orr Enterprises Ltd. Was registered with Bobby Orr (85% owner) as the 18-year-old President and Alan Eagleson (20% owner) as Vice President as a tax shelter and an investment vehicle for Orr.

The first important acquisition was a piece of land on Lake Couchiching, near Orillia, upon which sat an old resort called Owaissa Lodge.  The Orr-Walton Sports Camp was established at that site, and Mike Walton, a young prospect on the Toronto Maple Leafs and an Eagleson client, was brought in as Orr’s partner (5% owner).

In the early 1970’s Bobby Orr Enterprises invested in real estate companies, one of which was called Nanjill (named for Eagleson’s wife Nancy and daughter Jill).  In 1973, Bobby Orr Enterprises also funded a $125,000 mortgage on Eagleson’s Rosedale home in Toronto.  Bobby Orr Enterprises invested in Marty’s Custom Clothiers, a high-end men’s retail store in Downtown Toronto (Bobby's youngest brother Doug worked there).  There we also investments in a car wash, and Pony Sporting Goods Ltd.

In 1971, Bobby Orr Enterprises bought 60% of the Canadian closed-circuit TV rights for the Cassius Clay-Joe Frazier boxing fight for $250,000.

Bobby Orr did not have any bad habits, but he lived well and was especially generous to his family, giving members more than $200,000 in cash gifts during his playing days.  Between 1971 and 1979, Orr withdrew from Bobby Orr Enterprises a total of $1,134,741, most of it in after-tax dollars.

In 1978 Bobby Orr learned that he had tax problems.  Bobby Orr Enterprises was not recognized as a tax shelter by the Internal Revenue Service.

On Labour Day weekend 1979, Bobby Orr called Alan Eagleson at home late one night yelling and cursing at him, telling him how he had mistreated him, didn’t care about him anymore.  The following day, a meeting was set up at the apartment of a mutual friend in New York, and after much yelling and screaming, it was mutually agreed that the “partnership” was over.

Over the next several months, Bobby Orr began the process of extricating himself from Eagleson, during which he lived on deferred money from an earlier contract with the Bruins.  His only guaranteed income was a five-year endorsement deal with Standard Brands, a food conglomerate now owned by Nabisco, that paid him about $100,000 a year. It was money he needed, because when everything was added up, Bobby Orr Enterprises was worthless.

Eagleson, in trust, bought the assets of Bobby Orr Enterprises for about $620,000.  Those assets included $150,000 for Orr’s interest in Walker Heights, which principally owned seven acres of land near Collingwood, Ontario; $100,000 for his interest in a Toronto car wash; $40,000 for his interest in Nanjill, Eagleson’s real estate investment company; and $330,000 for the Orr-Walton Camp.  But with $285,000 in outstanding mortgages on the camp plus bank loans totaling about $450,000, Bobby Orr Enterprises showed up in the red.

On the afternoon of Saturday, September 8, 1973, Bobby Orr was married in what was widely described as a “secret ceremony” back in Parry Sound.

The bride was the former Margaret Louise Wood – known to all as Peggy – a former speech therapist who had grown up in Detroit and was now a resident of Fort Lauderdale, Florida.

Bobby had met her in a bar in Boston.  She was 26 and he was 25.  The wedding took place just before the beginning of the Bruins training camp.

Details were sparse because Bobby wanted it that way.  The reporters and photographers who were staking it out, having heard small-town rumours, were largely frustrated in their efforts to get the story.  Doug Sr. told them that morning that Bobby had gone fishing, and it turned out he wasn’t just trying to throw them off the scent.  Bobby had indeed escaped to the water for an hour or three.

He returned in plenty of time for the ceremony, which took place at the home of the Presbyterian minister’ Rev. Robert A. Crooks.  The bride wore a pale blue pantsuit, the groom a light-coloured business suit.

Bobby’s sister Pat was the maid of honour, and her husband, Gerald Murphy, was the best man.  There were no other guests.

"I signed Bobby Orr to his longest contract yet—till death do them part," noted the Rev. Robert A. Crooks, coach and manager of St. Andrews Presbyterian Church in Bobby's hometown, Parry Sound, Ontario.

“Peggy and I just decided on the date a few days ago.  I would liked to have had a big wedding for Peggy, but we decided to just do it…get in the church and get it over with,” Bobby explained later.

None of his Bruins teammates knew it was coming, though he’d let Harry Sinden in on the secret.

Miss Wood's parents could not get to the church on time so Bobby's parents accordingly decided they should not attend to be fair.  

The happy couple’s first stop as man and wife was for a short visit to the Orr family home.  A reception followed at the Parry Sound curling club at 8 PM.

Bobby and Peggy dropped in on Al and Nancy Eagleson the next day at their home in Toronto, on their way south, and then left for a short, pre-training camp honeymoon on Cape Cod.

After a two-day honeymoon, Orr showed up at Boston Garden for the closed-circuit telecast of the Ali-Norton fight—alone.  Probably not in the contract.

Eagleson distributed a wedding photo to the press.  It remains one of the very few pictures of Peggy Orr in public circulation.

Another story of Bobby Orr that shows why he was such a gift to us, took place in Oakland, California.

In a 1975 game against the Golden Seals, Orr took control of the puck while killing a penalty.

He circled a couple of times then rushed up the right side and shot.

The goalie, Gary Smith, made the save and the puck popped in the air.

While the puck floated in mid-air about chest level, Orr flicked his blade and the red light went on.

For the first time in major sports history, BOTH teams stood and applauded.

That is the type of respect that #4 commanded.

Angling, fishing, was Bobby’s second passion as a boy. Although his grandmother introduced Orr to fishing, he has fond memories of fishing with his father as a young boy. In the summers he loved to fish with his father and brothers.  Their favorite fishing spot was a place called Moon River.

He still loved fishing as an adult, and it still remains his passion today. Bobby Orr has travelled and fished all over the world. Over the years he fished in places in Australia, the Azores, Africa, and Venezuela, to name a few. When in Australia he caught an 800-lb. black marlin. But probably his favourite fishing is fresh water fishing -- salmon fishing and bass fishing in Canada. Growing up he spent a lot of time fishing on Georgian Bay, Lake Saint Francis, and the Saint Lawrence.

Bobby Orr's wife shares his passion for fishing, and is quite the angler. She enjoys fly fishing, and her biggest salmon catch is 35 lbs. Bobby Orr also has fond memories of fishing with his children. When his youngest son caught a barracuda in Florida once, they had it stuffed for a souvenir. Now, with his kids grown up Orr still gets out whenever he can. And while in Florida he really enjoys days out on the ocean, deep sea fishing.

In 1966 Bobby Orr Enterprises Ltd. Purchased a 180-acre tract of land on the east side of Lake Couchiching, near Orillia, upon which sat an old resort called Owaissa Lodge. 

The Orr-Walton Sports Camp was established at that site, and Mike Walton, a young prospect on the Toronto Maple Leafs and an Eagleson client, was brought in as Orr’s partner (5% owner). 

Bill Watters, a Toronto high school teacher who grew up in Orillia, was hired to run the Camp.  Tom Watt also assisted Bill Watters in Camp Director duties. Watters, and later Rick Curran, another camp employee, also developed a close relationship with Bobby Orr.  Orr and Walton became best friends.

Rounding out the family was Bobby’s father Doug Sr., who was convinced that he should quit his job at CIL in Parry Sound to take a Director role at the Camp, and Mike Walton’s father, who was appointed head of “clean up”.

At its peak, the Camp saw 700 students over the course of the summer, with every boy paying $125.  The kids got hockey instruction from the pros, and could also enjoy the more standard summer camp lineup of swimming and boating and the great outdoors.

A few miles down the road from the Orr-Walton Camp, there were two hotels in the rural hamlet of Atherley.  A visit by Orr and his entourage to the Atherley Arms which catered to a rock ‘n roll crowd and was better known as :The First”, or the Lakeview Hotel, which was called “The Second”, was viewed as one of the more important events of the summer, especially to a young girl if she got a chance to dance with Bobby Orr or one of his friends.

The Camp was shut down in 1988 as Alan Eagleson sold the property to a developer who later planned on building a subdivision.

In 1993 the property was still vacant and was for sale.