Captain of a Cup winner usually means being one of the best players on the team and having a major role in the Cup.
What we’re talking about here is more like a Lanny McDonald scenario where the player limps to the Cup and 1000 points at the end of an otherwise non-HOF career. It was one thing with McDonald, a beloved player in Toronto and Calgary who had the media push to get him over the line. That seems really unlikely for Benn.
Benn's a Team Canada guy. The OBC will favour him.
Most (not all) guys above the 1000 point line are in the Hall or will surely be there when they are eligible. Most of the exceptions are guys that never won the Cup. *If* he captains a Cup winner, that should be the push to get him over the line. He also has a piece of individual hardware (Art Ross).
I don't think his HHOF case is really any weaker than like Alfie or the Sedins.
And I love the Sedins. And again, I hate Benn. But the case seems straightforward to me.