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There are some real upsets possible in this. New York Rangers can win that series but i bet not many think so.
I don't think you could be all that surprised by any outcome as this is so unique you could almost flip a coin best of 5 winner. Despite Montreal 71 points taking on 86 point Pens, Price could steal a few games himself and Crosby could be golfing and that is the biggest mismatch.
I think these series because of the long layoff and the training camp in the middle you could almost be like the first 5 games of a new regular season than the last 5 games of one.
This season record of the each eastern team first 5 games of the regular season 2019-20
Toronto 2W-3L
Columbus 2-3
Carolina 5-0
Rangers 2-3
Pittsburgh 3-2
Montreal 2-3
Islanders 2-3
Florida 1-4
Only 2 Eastern teams started with a record > .500 Carolina and Pittsburgh with the majority starting 2-3 which makes for interesting 5 games series if that trend hold true.