One of the more intriguing storylines as this NHL season unfolds will be to observe how the Maple Leaf organization gels. Or doesn’t.

Since the days in the early 1990s when Steve Stavro and Don Giffin fought over whether to bring Cliff Fletcher to town – Giffin wanted him, Stavro didn’t and promised to fire him after he was brought in – the Leafs have pursued any number of curious choices and strategies when it came to building their organization.

Ken Dryden performed a GM search and then decided he himself was the best man for the job. Then he tried to make Mike Smith and Anders Hedberg get along. Pat Quinn, who barely spoke to Dryden during their years together, became GM but was eventually stripped of that title and asked to work as head coach under rookie John Ferguson Jr., his replacement.

Former head coach Ron Wilson, after agreeing to have his two longtime assistants fired the previous summer, announced his own contract extension on Twitter, then was fired two months later.

All creative approaches to building and developing an organization, that’s for sure.

So why should this year be any different?

Here’s what we’ve got:

The team is owned and operated by two giant communication companies who are essentially at war. Bell wanted Brian Burke fired, Rogers didn’t, but eventually went along with it. The club was forced to abstain from a league vote approving the new Rogers TV deal last winter because the two sides couldn’t agree.
The CEO, Tim Leiweke, has announced he wants out. Well, Elliotte Friedman of Sportsnet announced Leiweke wanted out, and then Leiweke ultimately confirmed it. He’ll be gone by next summer at the latest.
The president of the team, Brendan Shanahan, was hired by Leiweke, but Shanahan didn’t hire the current general manager, Dave Nonis, who reports directly to him.
Nonis didn’t have a hand in picking his new assistant GMs after the old ones were fired during the summer, and didn’t know former Soo GM Kyle Dubas at all before Shanahan hired him to work alongside him.
Several bloggers who were very critical of Nonis and head coach Randy Carlyle last season are now working in the team’s front office.
Nonis didn’t hire Carlyle, but he inherited him from Burke, who was fired 21 months ago.
Carlyle saw his coaching staff fired during the summer, and didn’t have any of his preferred choices for new assistants approved. He’s never worked with Steve Spott or Peter Horachek before.
That’s a lot of people who didn’t know each other before they were asked to work together, or didn’t hire the people who are now reporting to them. Shanahan didn’t hire Nonis, who didn’t hire his assistants or Carlyle, who didn’t hire his assistants.

If organizations depend on loyalty, strong connections and trust to succeed, the Leafs certainly have some internal challenges ahead of them.

How could possibly this not work?