Brendl and Lundmark don't belong anywhere near this discussion, and that is because of the context of their draft class. In that draft, you had Patrik Stefan go #1! Then, of course, the Sedin twins--the only really good thing to come from that round of the draft. Brendl and Lundmark were very reasonable picks where they were taken. I mean look at the rest of the round--the top picks behind Brendl were Tim Connolly (#5), Taylor Pyatt (#8), Barrett Jackman (#17), Nick Boynton (#21), and then Marty Havlat (#26). So other than Havlat, are we lamentin that we missed out on Taylor Pyatt? You can certainly make the case that trading for the spot where we picked Lundmark was unwise, but the picks themselves were okay for that draft. It's just that the draft was trash.
Also, I take issue with the idea that Jessiman was a sure thing to be anything at the NHL level other than a bottom-sixer. He always had skating issues (not as important then as it is now, but still) and while he had size, he didn't play a game commensurate to that size. In his draft year he was #20 among NA skaters in the CSS rankings, and while the Rangers were attracted to his size and his roots and allegedly had him #4 on their board, there was a damn good reason he was available to them at #12. Jessiman was a mid-to-late first round pick that had some question marks attached. Hurting his ankle obviously exacerbated his shitty skating, there's no doubt. But, even once he decided to start fighting a couple years after turning pro, he still was hardly a power forward. He didn't play that game at all. He played like he was six inches shorter and 40 pounds lighter. He was never a given to do anything.