When people try to over-intellectualize these things, they run the risk of forgetting some basic principles.
Such as human beings are influenced firstly not by reasoned debate but by impressions and repetition, along with reflected glory. Putting a deplorable person in a nice suit and presenting them on a famous television show can make them look more acceptable.
Wouldn't it be ironic if Milo manipulates Maher into agreeing with him and making Milo appear reasonable. Milo is an expert troll. There are many angles from which he can attack Maher's sense of reality - freedom of speech, being banned from speaking, "weak liberals who need safe spaces", Strong Men Love Controversial Opinions, etc etc.