Jeremy Roy aside, this type of stuff is said every year. "so and so was supposed to go X spots higher in the draft," but they didn't. The draft is mostly a crapshoot after the early part of the first, with the odds of drafting an nhl player generally going down the further into the draft you go. But they are mostly right about the picks when you think about it.
Roy was a 2nd round pick. I don't remember the exacts of the trade, but I'll put it this way: the odds of drafting an nhl player in rounds 2 and 3 is roughly equal (with the 2nd having a bit of an edge, obviously). If you had both a 2nd (~30%) and a 3rd (~25%), you'd have about the same odds as picking an nhl player between 21-30 overall (~55%). I'm willing to bet without even looking it up that we gave up more than a 3rd to move up to draft this supposed late 1st player (Roy). Now, if you really think he was supposed to go around 15th overall (which would fit into the 11-20 range //~60%) now we might be onto something, but that's assuming a lot.
I'll leave with this, if Wilson were to say pick up several 3rds for cheap then I'd say he's lowkey onto something.