Well, I suppose I'll just make my case....
Why Orillia should win this series!
1. Better Goaltending - Bernie Parent raises his game in the play-offs, but he raises it from being one of the worst starters in the draft. Turk Broda is probably a bit below average as a starter, but he also raises his game in the play-offs.
2. Better Coaching - Toe Blake is among the super-elite coaches. He's well-rounded and versatile, but he is also very well-suited to coaching this team's make-up. He was innovative in the use of centres to cover the whole ice, where he would use them to support the puck in all situations and have them drive the play on both sides of the puck. Bobby Clarke, Norm Ullman, and Ryan Kesler fit this strategy to a tee. Duke Keats isn't ideal, with his lack of speed, but his two way play and rambunctious style mean he would be ok.
Blake was also big on having his defensemen join the rush and help out on offense. With Eddie Shore, Roman Josi, and Babe Pratt spread across the pairs, he'll always have that offensive threat joining the rush.
3. Better Defensemen - Eddie Shore is the big difference-maker here.
4. Scoring Depth - Orillia has 3 pretty equal scoring lines, which makes it very difficult to deploy top checkers effectively against them. Also, Orillia has scoring threats on every defense pairing. Orillia is a team that should just come in waves.
5. Containing Lemieux - A huge part of Portland's offense runs through Mario Lemieux, so the priority will be to slow him down. Obviously, there's no shutting him down completely, but Toe Blake has several options to slow him down. First, and probably most obvious, is running Bobby Clarke in a head-to-head matchup. Clarke's elite defensively, but what would really make the difference is his relentless determination. Mario Lemieux was pretty lazy, so Clarke might be able to dominate the puck battles, and that's the best way to stop Lemieux - keep the puck off his stick.
Second is running out our third line. I think Dumart-Ullman-Provost is the best checking line in the draft, so using them in a match-up role would be optimal. They might not be as good in terms of pure defense as other lines, but they're all so well-rounded that they'd be a handful. Like Clarke, these guys could dominate puck battles and just wear down opposing stars.
Finally, Blake has the option of matching up either Zdeno Chara or Shea Weber to just punish Leimeux for a long 7 game series.
If anyone can come up with a game plan to limit Lemieux, its Toe Blake. He's got options.