The Pearson in those days, as you probably know, was a very low-prestige award, awarded in the media only (as far as I know) by the NHLPA, not even presented at NHL Awards night, and generally receiving scant attention. The definition of the award also changed from something like 'contribution to hockey' into 'best player in the NHL' at some indeterminate point in the early/mid-1980s, and since we haven't been able to determine that exactly in the internet era, I'm pretty sure the players back then didn't know about it either (nor really cared).
I think the players didn't take the Pearson overly seriously in the 70s/80s and into the 90s as well. That probably explains Lemieux in '86, Yzerman in '89, etc. It was more like the "players'-narrative" award.
I assume you meant '87, as Gretzky did win in '88.
I dunno... in 1983, he was the best player for sure and set the all-time records for points in a playoff year. Sounds great, right? But if your club gets swept in the Finals, should you win the MVP? I'm gonna say 'no'.
In 1987, Gretzky dominated scoring far less than usual (he was concussed throughout the Detroit series, I think), and there were just a lot of Edmonton players, plus Ron Hextall, who were stand-outs. So, I can see that one, too, even if I do sometimes tire of the "no-obvious-skater, so-let's-give-it-to-the-goalie" thing that kind of started with Hextall and became a common thing ever after.
I do know the Pearson was a bit different back then than it is today, yes. It's still a bit weird looking back and seeing such obvious seasons ignored.
For the Conn Smythe - you're right I meant 87 not 88, typo.
I agree with you on 83 - I mean I still think he could have/should have won - but being swept in finals didn't help a lot, and especially his low production (4 points in 4 games, which is bad for Gretzky). I think out of the 3 years I listed, it's the one I'm most understanding of him not winning. If he had scored more in the finals, even in a sweep, I'd say differently though.
84 - he should have won. Messier is great - but this was all about 'narrative'. Gretzky is the best and most valuable player for the Oilers in 84. You simply can't convince me otherwise, even though Messier played a very key role. Gretzky had most points in playoffs (including 9 more than Messier) and most points + goals in finals.
87 - I wasn't watching then, but I still don't get the Hextall win. Was he really that good? It doesn't seem so. It seems more like a "typical decent run by a #1 goalie who makes the final", and much less in the mold of a Giguere 2003 run, worthy of a smythe in a losing cause. Giguere won in a losing cause, and you can probably argue it's a top 5 goalie run of all-time (heck, maybe even #1). Is Hextall's run even a top 10 run of all time for a goalie? Top 20? I just don't really get it.
But what bothers me even more is that if you change Wayne Gretzky's name in the 1987 playoffs to Joe Smith, he 100% wins the Conn Smythe. Led playoffs in points by 6, 11 points in finals (2 more than anyone else)....he only didn't win because he was being held to too high a standard (ie his own previous 85 smythe). He was the best and most valuable player in the 1987 playoffs - and he should have won, it should be that simple.
To make a parallel to 87 - I was happy to see Sidney Crosby win the Smythe in 2017. Yeah the 2016 one has gotten enough press already - not the strongest smythe ever in a weaker year of candidates - but it would have been easy for voters in 2017 to say "well, he already got his smythe. Crosby is great, but he can do better as Crosby, so let's give it to someone else". No - instead, he was the best player (but not by a huge gap), and they voted for him accordingly, even if it meant him having 2 smythes in a row, they didn't try to hold him to a higher standard due to his name/previous win. I hate those 'narrative' political votes. MVP is MVP - keep it simple, Gretzky should have won in 1987.
If Pens had somehow won the cup in 93 with their powerhouse of a team - I wonder if they'd have tried to come up with a narrative to keep a 3rd smythe away from Lemieux (assuming he would be the obvious choice, which seems likely).