"Deplorable" comment is obviously intended strategy. It's right in line with alt-right attack theme.
The word choice is too deliberate, that's not the kind of phrase that just falls out of your mouth when talking to reporters. (Whether you happen to like the particular phrase or not.)
It's clearly meant to continue driving a wedge between GOP voters and make it "okay" for the normally GOP voting soccer mom in Bucks County PA or the Wall St Journal reading guy in Grosse Point, MI and Shaker Heights, OH who feel uncomfortable being on the same team as a torch wielding lynch mob to vote HRC, Gary Johnson, stay home or whatever rather than doing what habit and their sense of GOP "duty" normally would compel them to do.
Whether the strategy is good or effective remains to be seen, the potential drawback/backfire is if these same GOPers identify even more with their "team" and take the "deplorable" as aimed at them and turn out even more than they would have.
The other, probably intended, effect is that it will likely provoke the deplorable ones into acting, well, deplorably, in very visible ways that can be covered by media, emphasizing the point.
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