Thank you for mentioning Benn, who I think is a very strong candidate for the 151-200 range.
Jamie Benn is absolutely more worthy than Markus Naslund. Offensively, he's only a tiny bit behind in the regular season. 7 year VsX average: Naslund 82.9, Benn 81.4. 10 year VsX average: Naslund 73.9, Benn 71.2. And Benn kills Naslund in everything other than regular season offense. Not that Benn is a playoff god, but compared to Naslund...
IMO, Benn's legacy is extremely comparable to John LeClair's at this point. The distribution of their best offensive seasons is different (with Benn's Art Ross and LeClair having more top 10 seasons), but overall they average out to very similar production: 7 year VsX average: LeClair 81.7, Benn 81.4. They are actually dead even in 10 year VsX average, both with 71.2:
Reference - VsX comprehensive summary (1927 to 2020)
And in terms of style (power forwards but not especially mean ones) and play away from the puck, I see a lot of LeClair in Benn. Both good but not great in the playoffs too.
LeClair was ranked 49th on this forum's wingers list, and I think that is about where Benn should go too. I definitely prefer Benn to someone like Kovalchuk.
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Woody Dumart - was he better than Bert Olmstead, Rick Middleton, or Reg Noble - the bottom group of two-way winger to make the top 60 wingers list?
What about George Armstrong or Baldy Northcott, neither of whom made the list?
One of the problems with Dumart is that his playoff stats are so horrendous. So even if you give him a bit of a boost for loosing some prime years due to the war (which I agree, you should do!), he definitely gets docked some points for his playoff stats.
I do recall now that Dumart was one of those two-way wingers I was hoping to talk about in the final round of the wingers project, but never got a chance to. I just don't know if he makes it.
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@overpass covered George Hay. His All-Star record at LW is outstanding (and we did NOT have full records of this when we did the wingers project).
Hay's latest ATD bio does mention a two-way game more often than I expected it to:
ATD 2019 Bio Thread
I wasn't really thinking of him before, but I think I'll include him on my list, just because I think he's one player who really deserves a closer discussion in Round 2.