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.