It was a different time back then. Agents had really just begun to become prominent, with the first few literally a couple of years before Orr's arrival in Boston. I think it was Bob Woolf (sp?) in the Boston area who first represented a Red Sox pitcher named Earl Wilson in a contract negotiation in the mid-'60's, and parlayed it into being the first prominent full-time sports agent. Eagleson crapped on Orr financially, for sure, but he also crapped big-time on the NHLPA, and no doubt it was Orr's representation that got him that post. So the NHLPA membership probably resented the by-then-retired Orr for his guilt by association, until it became blatantly obvious that Eagleson had defrauded Orr to the tune of a 20% ownership stake in the B's.
I'm not sure how much an NHL franchise is worth these days, but 20% of an Original Six team has got to be at least knocking on the door of a nine-figure sum. Orr is hardly starving these days, and his work since that travesty has done much to ensure that no one falls into the same traps he fell into. But for a guy who was THE most transformative athlete in Boston sports history, to only exist on the fringes of the franchise he himself transformed from the outhouse to the penthouse two generations ago, still strikes me as kind of sad. That whole "Bib Bad Bruins" team, they were rock stars in their town, but when is the last time you ever saw the organization pull out all the stops to celebrate the likes of Orr, Esposito, Cheevers or even Sanderson??
There is a parallel with Gordie Howe, whom I believe Orr considered his hockey idol. The recent passing of former "Production Line" linemate Ted Lindsay saw the resurfacing of old stories about Lindsay's role in first trying (unsuccessfully) to unionize the NHL players in the late '50's. The Norris family who owned the dynastic Red Wings of the time would take advantage of Howe's financial naivete to set the ceiling for their salary structure, and use his modest salary to "cap" out the rest of the team under Howe. Lindsay figured this out, which got him traded out of Detroit, and in the end Howe resisted, convincing his teammates to scuttle the union effort. That frosted a great team, an historic line, and put their relationship on ice for several years. Howe eventually figured out he's been hosed, largely through wife Colleen's efforts, and he returned to play a couple years after he retired from DRW to cash in with his kids in Houston of the WHA.
One thing the Wings have over the B's is they've since laid out the red carpet to the royalty (and not-quite-royalty) among their alumni. By the time Mike Ilitch bought the Wings in the '80's they were the "Dead Wings" and no one cared, but he was a fan and spent like a fan, took chances with risky strategies (i.e. heavy recruitment in Europe before it was a "thing", and dicey activity behind the old Iron Curtain), and it all paid off in the end. And he went out of his way to bring back guys like Lindsay and Howe (amongst others) from the dynastic teams in the '50's (sadly, several like Terry Sawchuk had passed by then), who were regular visitors and attendees at DRW games in their later years. Lindsay was omnipresent up until his recent death.
But yeah, guys like Orr and Howe were the last vestiges of a time when sports agents and players unions were still new to the scene, and both paid a price at different times - in different ways - for getting caught out for their naivete. It's trite but true to say those were simpler times. It's a good thing players are no longer exploited like they were back in those days, but as a kid who grew up before the financial part of the games were so publicized, there are aspects of the old days - when all that really mattered as a fan was what happened on the ice, and everything else was just white noise - that I still miss. And it's one of the reasons why I've gravitated more and more to college hockey (and appreciate those "four year" players) as a result. JMHO.