Watching the phenomenal Hart Foundation vs Austin/Michaels period in mid-97 makes me wonder what Michaels vs Pillman would have looked like? Was Pillman too broken down at that point due to his heavy injuries? Would a 1992 Pillman vs 1997 HBK match almost guarantee a ***** affair?
I dunno, Shawn was always better with big guys who he could sell for. 97 Pillman was absolutely broken down past the point where anyone could have gotten a match out of him, sadly. Pillman's best uses were either as the plucky babyface fighting from underneath (see: Lex Luger at Havoc 89) or obnoxious shithead heel getting what's coming to him (what should have been the payoff of the Loose Cannon stuff that never came). It's not a dynamic that would work well with Shawn as an opponent, I don't think.
I'm actually doing a column on "What ifs" for The Sporting News this week, and I've got some ideas on what Pillman COULD have done if he was healthy that I'll throw in there.