I agree adma. Between bad management and bad press, I imagine Deco's sales aren't what they should be to sustain the lifestyles of the rich and infamous Fords. I wouldn't be surprised if money was one of the main reasons Dougie didn't run for the leadership. Even rich people can run out of money, especially when they need their various lawyers on speed dial.
"Family" companies that pass to children via inheritance have something of a chequered record (see, for example, Eaton's). The Fords and Deco always remind me of the mattress manufacturer that was built from nothing by my great uncle, and whose loudmouth asshole son subsequently ran it into the ground within a little more than a decade of his father's death. I even once had a summer job there in the shipping office. It was pretty terrible. Most of the employees on the floor were immigrants, and it taught me that the essence of "private enterprise" is to the bare minimum possible, and somehow wring a profit out of it.
Of course, it's not surprising that it went under - the workers weren't treated all that well; the shipping computer system was antiquated even in 2001; and, yes, that whole asshole thing.
In the end I don't think Doug is all that smart, even if he might beg to differ. Sure, he might have mounted a bid for PCPO leader, but I don't think his organizational skills extend to much more than attracting weirdos to Ford Fest events, and he's burned bridges with anyone with some semblance of professional political experience. Doug Ford, organizing across the province to win a convention? I can't say it. I'm not even sure he has the skills to sell memberships to win a local nomination battle; this guy doesn't understand process or rules or seem to recognize they exist.
As ever, we overestimate his "natural" support by referring to the mayoral election. Doug Ford benefited from an incumbency effect, and against a very different opponent in John Tory than he ever would with Wynne or Horvath. At the local level, he would be a loose cannon who would create problems for the party leadership which is hardly going to let itself get co-opted by a self-aggrandizing personality cult.
Fame is fleeting and 2017 is a long way from now. For the time being, I'd hope simply that Doug STFU and that we stop seeing his disingenuous smirk on TV. Forever.