Agreed. A 3rd Vezina would likely put him in the Hall of Fame despite team success. But you have to think/hope/pray that for at least 1 postseason it all comes together for him and the team.
Even 2 puts him in a pretty rarefied company. But it is interesting because now that Bobrovsky has won a cup. Helle is now one of 2 goalies with at least 2 Vezina's that has not won a Cup.
The only other one is Tony Esposito who played nearly his entire 16 year career with Chicago through the 70's to early 80's and never won a Cup. Tony had really only 1 solid playoff outing in his career when he lead the Hull/Makita Hawks to the Cup finals in 1971 on the back of a pretty amazing performance but they ultimately lost to Montreal in 7 games. They made it back in 1973 and again lost to the Habs in 6 games but his performance was pretty ho-hum that time around.
But he was still inducted into the HHOF in 1988, 4 years after he retired from the game.
Tony Esposito
3x Vezina
1x Calder
3x First Team All Star
2x Second Team All Star
1x Top 3 Hart Vote (no win)
886 GP - 423 Wins - 76 Shutouts
Connor Hellebuyck
2x Vezina
1x Jennings
2x First Team All Star
1x Second Team All Star
2x Top 3 Vezina Vote (no win)
518 GP - 287 Wins - 40 Shutouts
Esposito won most of his Vezinas before turning 30. After that he had some decent seasons but never really had the same level of play in his post 30 years old career.
Of the other goalies with at least 2 Vezina's that aren't in the Hall are;
Bobrosvky who is pretty much a lock to get in now with his Cup win and longevity as an elite goalie.
Tim Thomas who has a pretty amazing but very short resume and is also polarizing now. Going on 10 years now post retirement with no real word that he'll ever get in.
Charlie Hodge is the only other one but at the time he won his 2 Vezina's the award had very different criteria, it was more like the Jennings and so he split both of his with Gump Wrosley on the Habs. He never really had the individual play to get himself into the Hall unlike his platoon partner.
All this to say that even though Esposito never won a Cup he still landed in the Hall so I think if Helle wins another Vezina this year he's pretty much a lock. But only winning 2 with little playoff success to date could make him the only goalie with at least 2 Vezina's and No Cups and likely not a lock long term to make it in.