One of the other factors here, and I think a disadvantage to a lot of the cap-era teams, is the goaltending required to make it...
Re-purposing a post I made a dozen years ago (yeesh...)
90: Ranford/Moog
91: Barrasso/Casey
92: Barrasso vs. Belfour/Hasek
93: Roy/Hrudey
94: Richter/McLean
95: Brodeur/Vernon
96: Roy/Vanbiesbrouck
97: Vernon/Hextall
98: Osgood/Kolzig
99: Belfour/Hasek
2000: Brodeur/Belfour
01: Roy/Brodeur
02: Hasek/Irbe
03: Brodeur/Giguere
04: Khabibulin/Kiprusoff
gave way to...
2006: Ward vs. Roloson/Conklin/Markkanen - Upstart rookie Ward takes Gerber's job (then loses it, Gerber comes back and gets a shutout, then Ward takes back over and Ward wins the Smythe...?) vs. Roloson, a career journeyman who was hot then hurt...I had time for Markkanen back in the day.
2007: Giguere vs. Emery - Giguere, a system goalie, lacking in technical skills (but with good anticipation)...Emery a fringe goalie riding shotgun to an Ottawa team that features a very good defense that gets torn limb from limb in a two or four year stretch by opposing GMs...the amount of goaltender lateral movement in this series was at an all-time low.
2008: Osgood vs. Fleury - Career over-cocky attaboy Osgood plays behind one of the strongest teams (the strongest?) since the lockout, ends up being the only thing that gives the young Pens a chance...young Fleury helps will the team to the Finals, but has never been recognized as elite...
2009 Osgood vs. Fleury - Role reversal, Osgood plays better than in 2008 and loses out...Fleury has a few less bad breaks this time around...either way, a never-was vs. a will-he-ever-be...
2010: Niemi vs. Leighton - Another instance where the weakest link of a team is the goaltending (2007 losers, 2008 winners, 2009 losers same) with Antti Niemi who plays rather poorly throughout the Finals but is out-done in his horrificness by a career minor leaguer in Leighton who puts together a despicable performance and allows such a bad Cup clinching goal that no one on the planet would have guessed it went in until Patrick Kane was halfway down the rink...I'm guessing this will go down as the worst goalie matchup in Finals history, or at least I hope so...
2011: Thomas vs. Luongo - Career journeyman Thomas gets the W despite his best efforts vs. Montreal and Tampa Bay (and really even against Vancouver early in the series...Luongo, much-maligned for his past (though somewhat unjustified), clearly isn't the same goalie since being traded...not a terrible guy to make the Finals though I suppose..
2012: Quick vs. Brodeur - Finally, a decent goalie matchup. Well past his prime Brodeur vs. the young Quick...Kings team steamrolls everyone, Quick doesn't allow any game to get close...Brodeur does all he can, but when your number one defenseman is Marek Zidlicky, well, it's a wonder you won a playoff series at all...
2013: Crawford vs Rask - The very unathletic Crawford, riding the wave of an excellent team. Rask has a lot of talent, and some of the fastest legs going. He's a horrible skater, which limits some of his effectiveness. Boston goes to the Final with two different goalies, gets a Vezina to two different goalies in a three year stretch...reminds you of the mid 80's Flyers a bit.
2014: Quick vs Lundqvist - This is as good as it gets after The Big Sleep.
2015: Crawford vs Bishop/Vasilevskiy - Crawford is uninteresting. Bishop wavered in quality. When he wasn't lazy, he had some upside. It's rare for a goalie that tall to be able to close holes quickly enough. Vasy is a rookie at the time, so that's a big ask...he flashed brilliance, but the Lightning strived hard to protect him too.
2016: Murray vs Jones - As we pull ourselves out of DPE 2.0, these goalies were kind of a product of the time. A couple of goalies who were playing well enough on stronger teams. But as the game evolved, and low-angle shots became normalized, these goalies were ill-equipped to adapt properly. Being tall isn't a skill, and these two goalies leaned on it being so.
2017: Murray/Fleury vs Rinne - Fleury again...much more consistent than he was earlier in his career. Better positioning and a quieter game, but still with the reflexes and athleticism to steal a game - Flower was clearly in the Conn Smythe lead early in the ECF. Then the Pens quickly turn to Murray to finish it off. Rinne was talented, but again, like Bishop had a propensity to let things get through him. I have more time for Rinne than some goalie guys I know, some of them really don't like him.
2018: Holtby vs Fleury - Fleury again...Holtby was a good goalie for a short period of time. I think he got hit with injuries and it unwound pretty quickly on him...but he was excellent in the 2018 run. In fact, he personally deserved a better fate probably before this too. History probably will forget him, but he deserves a lot more credit than that...this was a good matchup from a technical point of view. Probably our best since 2014.
2019: Binnington vs Rask - Rask is Rask, he's a good goalie. Binnington is a really interesting case. Kind of has that Craig Anderson element to him...where he's good for a 45 save shutout or he's got an early shower after giving up 4 on 16. I'm not sure if the numbers hint that at all
@Doctor No but that's my feeling. This is another good matchup though. This isn't nearly as bad as what we had to deal with early on.
2020: Vasilevskiy vs Khudobin - Now, obviously, Khudobin seems weird there. And I agree to an extent. I've always really liked Khudobin believe it or not. But not necessarily a guy you want on this stage...but he's not as bad as history will remember. Maybe a bit like Irbe's run in '02. Vasilevskiy is basically the goalie of this mini-generation and that's on merit. He can be totally dominant. Like Hasek in some ways, including the odd propensity to give up a 40 foot wrist shot that comes with some pre-shot lateral movement.
2021: Vasilevskiy vs Price - Technically speaking, this is a historically amazing matchup. Two all-time "A" goalies. No one knows what .421 Montreal was doing in the Final, we'll all be sitting at a bar 10 years from now trying to recall how two Eastern teams were facing off in a Final to begin with...but regardless of how the series went, this is the pinnacle of goaltending. This was our Roy vs Brodeur from 20 years prior.
2022: Kuemper vs Vasilevskiy - Vasy again. Very justified. Kuemper...ok, fine, whatever. He's a guy that plays and he doesn't hurt you or really help you. He's just someone. He's miles better than Francouz, the scrambly backup who went like 6-0 in this playoffs. But still...he was just there.
So anyhow...all that to say there's a notable trough in there of goalies that were not overly talented and not very adaptable. And if we're actually playing these games, there's a bunch of guys pre-lockout that were very talented and very adaptable that would have a distinct advantage. Not to kill the premise of the thread, but just something that has really stuck out to me for a while now...