Can you think of a player that needed just one more great year - or even just one great playoff run or something else happening to them - that would have given them a rightful spot in the HHOF?
Here are a few that come to mind:
Theo Fleury - He might still get in. But if he finishes that 2001 season in where he is flying all over the ice then we are talking about a year where he could have cracked another 100 point year. Instead he unfortunately ended up in rehab. While he did win a Cup as a rookie in 1989, it wasn't "his" team so to speak. Had the Flames won in 1991 we are talking a different story here. Fleury always went above and beyond in the postseason in Calgary, but they got bounced out of the first round all of the time.
Rick Middleton - I don't even know if he needs a great season, because his career was every bit as good as Lanny McDonald's, I think, and Lanny got in on his first try. I would say this, there probably isn't a player who needed a Cup to secure his induction more than him. His final year his Bruins made the Cup final and got swept badly by the Oilers. A year later McDonald, who did less in the playoffs than Middleton did a year earlier in 1988, gets that famous critical goal in the deciding game (not the game winner like everyone thinks though, that was Gilmour the next period) and the vision we always have is him clenching his fist sitting over the Cup and then calling it a day. Look, I'd induct Lanny. He was physical, he was a sniper who scored 500 goals and his career totals are less stellar only because he got a slow start to his career and had a slow ending. His prime he was pretty darn good. And if Lanny isn't in today, I guarantee he is a name we often bring up as to why, similar to Middleton. But let me tell you something, if Middleton won a Cup, he's in there too. And I can trace it not to one season, but to one play that might have made the difference. Game 7 1979 vs. Montreal he has the game of his life, 4 points. He scored the go-ahead goal with a few minutes left. Then the Habs tie it and then in overtime Middleton is coming down the right wing, tries his usual nifty move in between the legs of a defenseman and gets turned away. That defenseman was Serge Savard. He sees it coming, takes the puck away from Middleton rather than have it go between his legs and passes it to centre where Rejean Houle tips it to a streaking Mario Tremblay who passes it to Yvon Lambert and into the net. Game over. I honestly think that singular play is what has kept him out of the HHOF. Think about it, Middleton could have fooled Savard and if he did he is in alone on Dryden who had a very shaky game. Middleton scores and that's his 5th point of the game and he is forever known as the guy who ended the Habs' dynasty. They play the Rangers in the final and they win. Middleton had 12 points that spring for Boston, only trailing Ratelle on the Bruins who had 13. There is a healthy chance he wins a Conn Smythe. Honestly, we are talking about a single play here.
Jeremy Roenick - Another guy who is in had his very good Hawks teams won the Cup. The image of "JR" being the leader on a popular Hawks team would be hard to forget. Sure there is Chelios who probably wins the Conn Smythe in 1992 anyway, but Roenick still makes an impact overall. But either way, his three 100+ point straight seasons lasted until Ovechkin tied it from 2007-'10. Then McDavid tied it in 2019. But still, incredibly no one has surpassed it since Roenick. Call it a perfect storm because we needed lockouts and injuries/retirements from having either one of Mario, Jagr, Gretzky, McDavid, Crosby, to pass it. Even Adam Oates needed one extra point in 1992 in order to have 5 straight 100+ point years, but it is still a big feat. But imagine him with another great season, either in Chicago or Phoenix. All of the sudden his career looks a little different.
Markus Naslund - It is a decent argument that he was the best player in the NHL from the 2001-'04 years. That's three years in a row. He's a first team all-star all three years at LW, he wins the Pearson Award in 2003 over Forsberg and in those three years his Hart voting was 2, 5, 5. Not bad. Is he making a much better case for himself if he has a great season in 2001 or in 2006? He was more or less an afterthought after the lockout and was never the same after Moore hit him, I don't think. Had a wicked wrist shot and I just can't understand how he was such a late bloomer, then had a huge three year peak, and then aged poorly. Does another elite season put him in the conversation?
Pete Mahovlich - While his two big years in 1975 and 1976 are often thought of as Lafleur-induced the truth is he still finished 7th in Hart voting in 1976. Meanwhile he finished 10th in 1971. So his stats aren't always an indicator of how he played. His penalty killing was important, as it was on Team Canada in 1972. Not to mention he comfortably makes Team Canada in 1976 as well. He is a 60-65 point guy with intangibles normally, and then a 105 and 117 point guy playing alongside Lafleur. Early in the 1978 season he is traded out of Montreal though. Does he need one, or maybe two, great seasons to get in? His stats are not terribly different from Steve Shutt, who is in, and who declined coincidentally at the same time Lafleur's constant injuries and shortened seasons kicked in. Big Pete was a strong force in the playoffs as well. I don't think 5 or 6 Cups makes a difference considering he already won 4. But maybe a couple more 100 point years?
Mike Liut - Does the stain of the 1981 Canada Cup forever get held against him? Or is another great season by Liut good enough? As it stands, it is him, not Billy Smith or Grant Fuhr, with the goalie that has the most wins in the 1980s, and these were not always with some very good teams. I could be wrong, but I think only he and Markus Naslund are the two players in NHL history with at least three seasons of being in the top 6 of Hart Trophy voting and not be in the HHOF. His Hart voting looks like this: 2, 3, 6. How many people even realize Liut finished 3rd in Hart Trophy voting behind Gretzky and Bourque in 1987? His Vezina voting looks like this: 1, 2, 3, 5, 7. That's pretty darn good, and he isn't the only goalie that would be in the HHOF with a mediocre playoff record. Then again, if his great seasons are often forgotten, would it be that easy to remember him having a Hart-caliber year in 1988?