Yeah, I find it hard to get a read on this. I certainly get the idea that it looks naive and it looks as if he's not receiving good counsel. But on the other hand, imagine how easily he could end up on CBC at prime time saying things like this:

"yes, that's right, I wanted to create this tool because I kept running into people who had worked hard to acquire a ton of Aeroplan points, and had focused on acquiring frequent flyer status with Air Canada, but they found they just couldn't use the points. They tried, they just couldn't. I think on Westjet and Porter it's easy, from what I hear, but with AC it seems really hard. The Aeroplan chart said they should be able to fly to visit grandma for 50,000 points, but all they could find were flights for 400,000 points. That just didn't seem right, it seemed there was a real need for people to be able to book flight redemptions at sensible prices, which is what they had expected to be able to do. But the AC search engine isn't set up to really allow this, at least for most folks. Personally I don't think Air Canada was trying to rip people off with a bait and switch. I know a lot of folks think that, people keep saying it to me. But I think their search engine just wasn't set up properly and that I could help people find good redemptions, and I figured AC wouldn't mind. I tried to contact them to work with them but never heard back, I figured it was just because I was a little guy, I mean it's literally just me in my basement trying to present AC's fare information in a way that helps people." Etc.

Then the CBC could run out and add colour to the story by finding a bunch of people who had paid, or only been able to find, absolutely absurd prices for their redemptions. They could very easily round out the story with clips from FFs who are annoyed about other things, like 25k and 35k folk who are at the bottom of eupgrade lists that are 30 people long, folk stuck in lines for lounges, and so on. This wouldn't be because CBC was setting out to do a hatchet job but because it's a compelling narrative arc, especially once it's been teed up by a little guy getting hammered by AC because he was trying to help someone visit grandma for a reasonable price. And clips of things like crazy long lines at lounges, recording of AC searches that show 400,000 points needed for a redemption, etc., are all visual material and they'd want to add that to the story.

If I were Aeroplan I would be very worried about the above since he could do significant repetitional damage to them, and completely by saying things that are clearly fair comment/opinion. He couldn't have done that before since he was a nobody. But he certainly will be able to now given that they are busy making him famous.

(To be clear, I have no view on whether they should have filed the suit or not, whether their claims are justified, etc. )