I think the Pirates have a clear advantage down the middle at C, especially the top line and 3rd line. LW is about even in my estimation, top to bottom, although Lindsay is the best LW in this matchup.
From a scoring standpoint the Eagles have a strong advantage at RW, up and down the lines, but the Pirates counter with strong defensive play in the bottom 6 with Provost and Westfall.
The Eagles have a good advantage on the top pairing but I think the Pirates are deeper 3 through 6.
I think Chara is probably a little better when you factor in he loses less of his career than Cleghorn does by the rules here, but the gap isn't huge. The big gap is between Horton and Horner, where the former has a large advantage, in an all time manner, at least IMO.
And then the bottom pairing should favor the Pirates as well, not only because I think Reardon-Bouchard are superior to Pratt-Heller but they also played together extensively in real life.
And then you have to factor in the absolutely insane amount of physical play the Eagles will have to endure vs all 3 pairings, in particular from Ching Johnson, Cleghorn, Horton, Reardon and Bouchard.
In goal, the Pirates hold the advantage if you like playoff stats and resume. Even taking away his Colorado time, Roy has 2 Conn Smythe's and the bulk of his regular season successes and trophies/AS nods came in Montreal. Glenn Hall looses his Conn Smythe from St Louis and that was his peak performance in the postseason as a player. He is clearly ahead in regular season, but well behind as a postseason netminder. Call it an overall wash, but I like the goalie who excels in crunch time!
Toe Blake gives the Pirates a slight advantage behind the net.
Close series, but of course I like the Pirates in a deciding game 7