The following is my attempt to categorize the Conn Smythe winners since 1980 (the start of the four-round era). I'm using four tiers, which can roughly be categorized as Godlike; strong victory; solid victory; and undeserving. There's still a range within each tier, but when I tried to divide it into five categories, it felt too complicated. Remember that the third tier represents deserving, worthy winners (it's not an insult for anybody to be in that category). Players are presented chronologically within each tier.
In assessing the trophy recipients, I'm taking two aspects into account. The first is trying to objectively assess the level of performance (ie how well did they play). The second is trying to assess the relative level of performance (ie did someone else have an even better playoff run that year).
(Full disclosure - I'm stealing the premise from another thread (link), but I think a 4,000 word post should get its own thread).
- Gretzky (1985). This is the highest-scoring playoff run of all-time. Yes, it was in a high-scoring era, but nobody aside from Lemieux and one of Gretzky's teammates has come within ten points of this. Beyond the raw numbers, what stands out is Gretzky's remarkable consistency. He was only held scoreless in two of eighteen games (Edmonton lost both games, which shows his importance to the team). He also had a killer instinct. In the the four games where Edmonton could eliminate their opponent (which they did each time), he scored a total of 17 points (with at least two in each match).
- Roy (1986). Montreal wasn't quite as bad in the regular season as some people have suggested, but that doesn't detract from Roy's brilliant performance. He posted numbers that would get him Conn Smythe attention today, at the height of the Air Hockey Era. Roy's consistency - a factor that we see again and against throughout his playoff career - is already evident here. He never had two bad games in a row. Based on adjusted save percentage (see Goalies: Adjusted Playoff Save Percentage), Roy posted the second-best performance from any Smythe-winning netminder.
- Grezky (1988). The ultimate display of consistency. Gretzky was held off the scoresheet just once in 19 contests. After an unspectacular start (by his high standards), Gretzky scored 26 points in the last 10 games against Detroit (the team that allowed the fewest regular season goals against in their conference) and Boston (3rd fewest in their conference). Gretzky scored 13 points in the Stanley Cup finals alone - yet another record that he solely possesses.
- Lemieux (1991). Lemieux became the only player other than Gretzky to scored 40+ points in a single postseason. Visually, this might be the most impressive playoff run of all-time. Le Magnifique truly looked like a man playing against boys. He got better as the playoffs progressed (scoring a ludicrous 26 points over the final 10 games). Pittsburgh lost the only game he missed. Barasso was excellent this spring, and in many other years he would have gotten serious Smythe consideration, but not against peak Lemieux.
- Roy (1993). Remember before when I said that Roy's 1986 campaign had the second highest (era-adjusted) save percentage among all Smythe-winning goalies? Roy was runner-up to himself - this season ranks first all-time in that regard. Everyone knows that this was the spring where Roy had ten straight overtime victories. To me, that's not even the most impressive part. This was perhaps the most consistent display of elite goaltending in playoff history (at least dating back to 1980 - hard to compare this to, say, Sawchuk in 1952). Roy had, by my count, just two games where he let a victory slip away, or his team won in spite of him. Other than that, he was unfailingly great, all the way through. Fun fact - Roy posted these amazing numbers while facing four of the top six teams in regular season goals for.
- Giguere (2003). The greatest performance through three rounds in NHL playoff history. I've never seen a single player carry a team the way that Giguere did. Look at their roster - Keith Carney, Ruslan Salei and Niclas Havelid averaged 25+ minutes per game, while their sole star, Paul Kariya, scored just 12 points in 21 games. Giguere helped his team sweep Detroit (the defending Stanley Cup champions, second in the conference) in the first round by stopping 96.5% of the shots he faced. After shutting down Dallas (the conference champions) in the next round, he embarrassed Minnesota by holding them to a single goal in a four-game sweep (stopping all but one of the 123 shots faced). It's true that Giguere was merely average in the Stanley Cup finals - and yes, I know that's the most important series - but he accomplished enough that he deserves a spot in the top tier. Scott Niedermayer (who would go on to win a weak Smythe in a few more years) was the top candidate for the Devils, but he was a very distant second.
- Trottier (1980). A dominant (and underrated) performance for the Islanders centre, who was a physical two-way force. In addition to leading the playoffs in goals (tied) and points (decisively), he was on the ice for just 13 even-strength goals against in 21 games in a high-scoring era. He also played on the Islanders' penalty kill. The only strike against him is he was scoreless in three of the four games in the first round (though, I suppose, if you're going to a struggle in any one round, better for it to be the first).
- MacInnis (1989). Everyone remembers MacInnis for his devastating slapshot, which is a shame, because it overshadows what an intelligent, complete defenseman he was. The second best hockey player from Nova Scotia easily led the playoffs in scoring, while being on the ice for only 11 even-strength goals against in 22 games (in a high-scoring era). MacInnis is the only player other than Gretzky to score more than 20 powerplay points in a single playoff run. There were a lot of strong performers both on the Flames and Canadiens, but Chopper was definitely the most deserving.
- Lemieux (1992). On a per-game basis, Lemieux was even better than in 1991. He scored at least two points in nearly three-quarters of his games - a stunning accomplishment. But two strikes keep this out of the top tier. First, he missed six games, and Pittsburgh did well (going 4-2) when Lemieux was out. Second, exactly half of Lemieux's points came in the first round against the overmatched Capitals, so his performance beyond the first round was (comparatively) less impressive.
- Leetch (1994). The first non-Canadian to win the Conn Smythe trophy. Leetch was one of only a small handful of defensemen to ever lead the postseason in scoring. This run wasn't notable just for his offense though; Leetch played perhaps the best defensive hockey of his career and was a strong presence at even-strength, on the powerplay, and on the penalty kill. No player has ever been on the ice for more goals for in a single playoff run. Everyone remembers Messier's guaranteed victory, but it was actually Leetch who decisively led the SCF in scoring.
- Sakic (1996). After having the best regular season of his career (which he later surpassed in 2001), Sakic had a historic playoff run. His 18 goals are the 3rd highest single-season total (and, adjusted for era, is also probably hovering around the top five). He also has the 2nd highest scoring total of the "lockout era" (from 1996 onwards). Despite not yet being recognized as a two-way force, Sakic was only on the ice for 13 even-strength goals against in 22 games. He scored two of his all-time record eight overtime goals this spring. The only argument against Sakic is he was underwhelming in the anticlamactic finale against Florida (scoreless in two of the four games).
- Roy (2001). Although the least impressive of his three Smythes, this was still an excellent playoff run. Roy was surprisingly mediocre in the first round against Vancouver (but Colorado swept them anyway), but was stellar from there. What stands out is how his level of play rose during the biggest games. In game 7 against Los Angeles in round 2, he stopped 25 of 26 shots. In games 6 and 7 against New Jersey in the Stanley Cup final (when a loss would end their season), Roy stopped 49 out of 50 shots. The only argument against Roy was that Sakic was just as deserving of the trophy (especially for his work over the last two rounds, where he scored 17 points in 12 games against two of the league's best defensive teams).
- Zetterberg (2008). I'll admit that I didn't fully appreciate this performance at the time but, looking back a decade later, I firmly believe that this is in the second tier. His offensive stats are good enough - Zetterberg tied for the playoff lead in both goals and points. After a slow start against Nashville, he was excellent from round two onwards (he scored at a 118 point pace per 82 games from rounds two through four). But his defensive performance is what pushes him to the second tier. He was on the ice for just 7 even-strength goals against in 22 games, while also being a key contributor to the Red Wings' penalty kill. Zetterberg also slowed Crosby down (he was held to 1.00 PPG in the finals after scoring 1.50 PPG in the first three rounds).
- Malkin (2009). A brilliant offensive performance by the frustratingly inconsistent Russian centre. Malkin has the highest-scoring playoff run from the lockout era (1995 onwards) and, adjusted for era, is within striking distance of peak Gretzky and Lemieux. Although his production decreased in the Stanley Cup finals (relative to the previous three rounds), he still led that series in scoring. The only argument against him is Crosby had a case for the Smythe as well (Crosby was five points behind, but generally faced tougher opposition, and was on the ice for significantly fewer goals against).
- Thomas (2011). Thomas was outstanding for Boston this spring. Although it's true that he played behind a strong, disciplined team, Thomas deserves credit for his high level of play. Although the first few games against Montreal in round 1 were shaky, he was exceptional after that (94.5% save percentage from game 5 of the first round onwards). He stopped 95 of 98 shots in three game seven victories (including a shutout in game seven of the Stanley Cup finals). Two of his losses in the Stanley Cup finals came after he allowed 2 goals on a combined 59 shots. Still, both Chara and Bergeron deserved serious Smythe consideration.
- Quick (2012). The Kings steamrolled their opponents this year, losing just four times en route to the Stanley Cup. Quick was remarkably consistent, posting between a 93.9% and 95.9% save percentage in all four series. Quick helped shut the door completely (the Kings were 9-0 when leading after two periods). Still, Kopitar (tied for the lead in scoring, and ridiculously low ES goals against) was worthy of the trophy, and Doughthy wasn't far behind.
- Keith (2015). My first impression was this was the strongest playoff performance of the 2010's. Keith played an enormous amount of ice time (over 31 minutes per game), and was only a few points behind the playoff scoring lead. But he was on the ice for quite a few more goals against than I recalled. I still think he's in the second tier, but probably farther down than I first expected.
- Bossy (1982). During what was clearly his best season, Bossy decisively led the playoffs in goals after scoring 147 points in the regular season. He was particularly good in the Stanley Cup finals, where he scored seven goals in just four games (that ties him for the record with Beliveau in 1956 and Gretzky in 1985 - but they both required an extra game). The main strike against him his centre, Bryan Trottier, posted better numbers overall, and he also played on the penalty kill.
- Smith (1983). The Islanders were a remarkably deep team. This year, more than any other, was a victory by committee. The Islanders, as a whole, never faced any serious threats, never trailed in a series, and they even contained Gretzky in the Stanley Cup finals and swept the up-and-coming Oilers. Remarkably, six of the Islanders scored 20+ points that spring! Potvin probably deserved the Smythe (he scored over a point per game from the blueline, and his superb work in the Stanley Cup finals was key to containing Gretzky - who was held to just four assists in four games). Still, Smith was very solid (even though he usually didn't need to be), and this was probably the best of his performances during the Isles' Drive for Five.
- Messier (1984). I've got nothing against Messier. He was a strong performer this spring, similar to Trottier's 1980 run in terms of style and results. But I can't list him any higher than Tier 3, because, in my mind, Gretzky clearly deserved the Smythe. Yes, Messier was a vocal leader in the dressing room, he was a ferocious hitter, and he was better defensively, but the gap in their production is too large to ignore - especially since Gretzky put up his comical numbers while facing the opponents' top defensive players. Note that Messier was held scoreless in three of the five games in the Stanley Cup finals (including the decisive game five, where Gretzky score two and set up Linseman as well).
- Yzerman (1998). The previous spring cemented Yzerman's legacy (he had been Detroit's captain for 11 years at that point, and helped them win their first Stanley Cup since the Eisenhower administration). Still, this helped the centre, previously criticized as a choker, permanently erase any doubts about his leadership or ability to play under pressure. An obvious choice, Yzerman led the playoffs in scoring, and was on the ice for only 10 ES goals against in 22 games. A close call, but I'm leaving this in the third tier because he stumbled against Dallas (a major rival), and his goal-scoring was disappointing.
- Stevens (2000). Perhaps more than any player on this list, Stevens' impact is hard to quantify. Despite a minimal focus on offense (five of his eleven points came in the first round), the Devils captain was a superb defensive player, who used his size and strength to frustrate, intimidate and contain the opponents' top players. In the second round against Toronto, Stevens helped hold Sundin to a single assist in six games. Stevens was a ferocious hitter, and the goals against numbers support his defensive reputation (15 even-strength goals against in 23 games, despite heavy minutes against top opponents). Despite his reputation for being dirty, he took just three minor penalties that spring.
- Lidstrom (2002). The great Swedish defenseman played an enormous amount of ice time that spring (he averaged over 31 minutes per game - going back to 1999, when ice time was first officially tracked, only Pronger in 1999 averaged more ice time per game - minimum 500 minutes). His (fluke) goal against Vancouver in game 3 of the first round helped the Red Wings bounce back from a 2-0 series deficit. They didn't look back from there. Lidstrom was a balanced contributor, playing very well both offensively and defensively. Still, this was very much a victory by committee for the Red Wings, with Yzerman getting serious discussion for the Smythe, with some support for Fedorov, Hull and Hasek as well. (Forsberg was so good that there was even some talk that he might deserve it, despite being eliminated in the conference finals).
- Richards (2004). A lot of people cited Richards' seven game-winning goals as the reason for him winning the Smythe. That's a bad statistic; a few of those goals were clutch (including two overtime markers), but others weren't (there was a goal that made it 3-0 before Philadelphia mounted a comeback that fell short, and another goal scored four minutes into a game where Khabibulin recorded a shutout - not really game winners in a meaningful sense). Even if the reasoning is poor, the result was fine. Richards led the playoffs in scoring, was consistent round after round, and dominated Game 6 of the Stanley Cup finals to keep the Lightning's season alive.
- Crosby (2017). A much stronger Smythe than 2016 (which you'll see below). Heading into this spring, the biggest black mark on Crosby's playoff resume was poor scoring in the Stanley Cup finals (just 13 points in 19 games). Crosby stepped up and recorded 7 points in that series (it was his first time, in four attempts, leading the finals in scoring). He was consistent from round to round. Despite his plus/minus improving, Crosby's defensive performance wasn't any better compared to 2016 (but his even-strength scoring increased).
- Ovechkin (2018). An excellent goal-scoring performance (adjusted for era, his 15 goals likely ends up in the top ten all-time). He was on the ice for 21 powerplay goals for (tied with Sakic in 1996 for the most during the lockout era), and played some of the best defensive hockey of his career (faint praise, but positive nonetheless). The Russian winger was consistent from round to round, and slayed two demons - he finally escaped the second round, and also defeated the rival Penguins. Still, Evgeny Kuznetsov was more deserving of the trophy (better offensive numbers while being on the ice for a comparable number of goals against), as was Braden Holtby (a strong and consistent performance).
- Goring (1981). This is the first in a long line of Conn Smythe selections that can only be described as puzzling. Goring performed admirably this spring, adding depth scoring and logging an enormous amount of ice time on the penalty kill. He also played well in the Stanley Cup finals (five goals and two assists in five games). But there's simply no justification in picking him over Mike Bossy (who outscored him by 15 points in 18 games - and led the finals in scoring) or Denis Potvin (who, in addition to scoring well over a point per game from the blueline, was on the ice for just 7 even-strength goals against in 18 games, and was only one point behind Goring in the finals).
- Hextall (1987). Continuing the trend from 1984, the voters seemed to be doing anything possible to avoid giving Gretzky the Smythe. No disrespect to Hextall - he put up fairly good numbers for the era, especially when you consider that seven of those games are against arguably the greatest offense in NHL history. But Gretzky was clearly the best player this spring, leading the postseason in scoring for the fourth time in five years. Hextall played very well in the finals, but even then, Gretzky scored twelve points in six games, so how much did he really slow him down? I'm guessing Hextall got a boost in the voting by virtue of being a rookie.
- Ranford (1990). Goalies seem to get the benefit of the doubt in many cases when there are many solid candidates, but no front-runner. This was the case in 1990, when the post-Gretzky Oilers surprisingly won Lord Stanley's mug. Ranford played well - he was probably the best netminder that spring - but he wasn't exceptional. It's my belief that a goalie really should be exceptional to win the Smythe. I would have gone with Messier (tied for the playoff scoring lead, with lots of intangibles) or perhaps two forwards who weren't too far behind - Kurri (who provided great defense) or Tikkanen (one of the most notorious pests in the sport's history).
- Lemieux (1995). The second most famous Lemieux to win a Conn Smythe was simply a bad pick. Tough and scrappy, Lemieux scored a lot of goals, but due to his relatively poor playmaking, he was only fourth on his own team in scoring. He was also on the ice for significantly more even-strength goals against than any of the teammates who outscored him. Martin Brodeur was outstanding that spring and even though he struggled in the conference finals against Philadelphia, he was clearly more deserving of the trophy.
- Vernon (1997). See my commentary on Ranford in 1990. Detroit cruised to the Cup, going 16-4, with a lot of important contributors, so the voters did the easy thing and picked the goalie. Vernon played well that spring, but he wasn't as good as his number suggested. Fedorov was clearly more deserving of the Smythe (Detroit's highest scoring player, while being on the ice for just 7 even-strength goals against in 20 games).
- Nieuwendyk (1999). The Stars centre got a lot of mileage out of the fact that he had six game-winning goals - but unlike Richards (2004), discussed above, his numbers were actually indicative of clutch scoring. Nieuwendyk had two overtime goals, and three more go-ahead goals in the last 11 minutes of third periods. That's the good news; the bad news is Nieuwendyk wasn't even the best centre on his team. Modano actually outscored him, and was trusted with more than six minutes of additional ice time per game, about half of which was on the penalty kill. Modano also decisively outscored Nieuwendyk in the Stanley Cup Finals. In addition, both goalies in the finals (Belfour and Hasek) were stellar and deserved serious consideration for the Smythe.
- Ward (2006). At the risk of repeating myself, see the commentary on Ranford in 1990 (or Vernon in 1997). Ward was very good this year, but a goalie should be more than very good to earn the Smythe. I would have given the trophy to Rod Brind'Amour (solid offense and excellent two-way play) or Eric Staal (strong offensive output, and stepped up in the SCF).
- Niedermayer (2007). There would be question marks about whoever won the trophy this year, as this was very much a team effort. The argument against Niedermayer is he pretty clearly wasn't the best defenseman on his team. Pronger was definitely better, but he also missed two games, and the Ducks won both, which led some to question how valuable he really was. (Anaheim scored 8 goals during the two games Pronger missed - and no, I don't think that him missing time somehow made them a better offensive team). Other candidates discussed included Giguere (very good, but there was no way he was getting another Smythe after 2003 unless he walked on water), Samuel Pahlsson (the Smythe is tough for a defensive forward to win unless you're Bob Gainey - and even then, his offense skyrocketed that spring), or Daniel Alfredsson (a strong run, but not good enough to deserve the Smythe in a losing cause). Niedermayer was very good, of course, but he's lucky Pronger got suspended twice.
- Toews (2010). At a first glance this looks fine - Toews led his team in scoring, was one point off the playoff lead, and has loads of intangibles. Here's the bad news - he was on the ice for a lot of even-strength goals against, and his offense dried up in the Stanley Cup finals (just three assists in six games). Kane, who had very similar numbers but was excellent in the finals, was more deserving.
- Kane (2013). A very low-scoring year; only five of the scoring leaders scored more than a point per game, and four of them were eliminated in the conference finals. Kane seems to have won the trophy by default (highest scorer on the team - and perhaps partly to make up for not getting the award in 2010). This is one of the few times where I think a goalie was shortchanged; Crawford played very well that spring, and was consistent from round to round.
- Williams (2014). I realize the writers sometimes try to pick a secondary player who stands out, but this wasn't a good selection. Williams wasn't even the Kings' best forward, as Anze Kopitar was clearly a bigger catalyst to the team, and entrusted with more ice time in all three situations. Kopitar (narrowly) outscored Williams, was better defensively at even-strength, and a significant contributor to the penalty kill. The argument in favour of Williams is clutch scoring, and I don't deny that; but Kopitar also played well at key moments (both scored 5 points during their three game seven victories; both had two points on overtime goals).
- Crosby (2016). If we're looking at the objective level of performance, this is probably the weakest showing on the list. Crosby scored at a level far below expectations (equivalent to 65 points over an 82 game season). His goal-scoring simply vanished, as he found the twine just three times over the last twenty games of the postseason. He only had four points in the Stanley Cup finals. People noted that he has the worst plus/minus of any Smythe winner; his ES goals against numbers aren't terrible though (the plus/minus is mostly a result of weak ES offense). This felt like a lifetime achievement award for Crosby. The only thing that keeps this from being the weakest Smythe of the past four decades is there wasn't a ton of competition for the award (still, I would have given the trophy to Kessel, who outscored Crosby, and was on the ice for significantly fewer goals against).