I know Ashton *wants* to be associated with Bernie, but that doesn't mean she will be.
who do you guys predict wins the NDP leadership?
I think Singh is a shoo-in. Some people may be annoyed that he's holding off until after the BC election, but a race like this is purely about who can sign up the most people. He's from just outside Toronto, plus he's plugged into the Sikh community, and those two factors should mean he'll have access to more people than anyone else in the race. It's possible Angus or Ashton somehow pull off a miracle, but right now, even though he's not even officially announced, I think Singh is the front-runner.
I maintain that I think O'Leary will win this easily
It definitely won't be easy with 14 people on the ballot. Best case scenario for him -- or anyone else, really -- is winning on the 6th or 7th ballot, and even that would be pushing it. I think it goes 10 or 11 rounds, and whoever wins just squeaks past 50%+1.
And I don't think O'Leary does it. He's basically writing off one-third of the country to start off. Even if some of the tiny Quebec ridings are ripe for picking off, I don't think he can do that over Bernier or, with Deltell's endorsement, O'Toole. That means that he has to win the rest of the country by huge margins, and in a competitive race with 13 other people -- almost all of whom have home riding advantages, unlike him -- that's practically impossible. I'm not saying it's guaranteed that O'Leary loses, but I think that's much, much more likely than him winning.
Ideally? The party disappears into the ether.
Realistically? Michael Chong since, however obscene his tax plan may be, he's the only one to seem palatable as a leader. I would never vote for him but I wouldn't be terrified of his leadership like I would for a Leitch/O'Leary leadership.
Also: Let's not get cocky in thinking Leitch couldn't win the 2019 election. It's too early to tell how any of the three party's will fare when there's two more years for the Liberals to deliver/fail to follow through on their campaign promises. Electoral reform may have been minor but if they back off from decriminalizing and legalizing marijuana? The Liberals will have a problem on their hand if they drop that.
Realistically, Michael Chong is not winning the leadership. Realistically, he drops off the ballot after Obhrai / Peterson / Saxton / Trost / Lemieux / Alexander / Blaney, but before the top 6 candidates (being Bernier, O'Leary, Scheer, Raitt, O'Toole, and Leitch).
I think that from a nonpartisan/good of the country perspective, someone like Raitt or O'Toole would be ideal. They hold some pretty terrible beliefs, particularly on the environment, but they generally believe in having a government that functions normally, which is more than can be said for most of the candidates. I wouldn't like a lot of what they do, but I also wouldn't be terrified that I'd wake up one day to discover that healthcare was ending (like Bernier), minorities were being rounded up in internment camps (Leitch), or the country had been sold off to pay off pyramid scheme debts (O'Leary).