I think he should be in the conversation, but even more than the high scoring forwards I think his team being second in goals per game will hurt him. If you go back to the last wins from Price and Theodore, Montreal was 20th and 19th in goals for, and even Buffalo was 17th and 13th in Hasek’s wins.
If we look at top 3 Hart finishes for goalies, the Rangers were 16th (Shesterkin in ‘22), Columbus was 6th (Bobrovsky in ‘17), Rangers again were 11th (Lundqvist in ‘12), Canucks were 21st (Luongo in ‘07), Jersey was 27th (Brodeur in ‘07), Calgary was 27th (Kipper in ‘06), Jersey was 14th (Brodeur in both ‘03 and ‘04), Colorado was 18th (Roy in ‘02), Buffalo was 17th, 18th and 11th (Hasek in ‘99, ‘95 and ‘94), Montreal was 14th (Roy in ‘92), Chicago was 8th (Belfour in ‘91).
You have to go back to Fuhr in ‘88 where the Oilers were 2nd in goals to find a goalie top 3 in Hart voting on a top 5 scoring team, and only two teams were top 10 in that time frame. If Winnipeg was 10-15th in goals for I think he’d have a much better chance, and a fairly decent one if they were in the bottom half of the league.