@Mikedarnay doing big time work here. He broke down the winners of multi awards all the way back to 90-91. Here is his breakdown.
Malkin is looking at winning multiple offensive trophies (Art Ross & Hart). Pretty exclusive company.This here in bold, shows other guys since 90-91 who have won multiples.Didn't count the Calder.Rocket Richard only became official in 98-99 but still grabbed top goal scorer.Malkin and Lemieux only 2 guys to win multiples including the Conn Smythe.Malkin, Lemieux, and St. Louis the only 3 to win multiples AND the Cup.Ovechkin in 08-09 only guy to win 3 in the same season.Didn't go back any farther to see Gretzky's stats.Enjoy.