Trump and HRC worked very hard in the last days of the campaign both clocking up thousands of miles in their planes going to rallies in the swing states. It is hard to believe that Trump was completely surprised by his win. Would he have worked so hard in the last day or two if he expected to lose? There were things like all the yard signs for Trump and Pence in the swing states and not many for HRC. Truck drivers were reporting on this all the time. Anecdotal evidence of a ground swell for Trump maybe, but the indicators were there unless you kept the TV on CNN!
TBH I felt when he won he was surprised. A political savvy opponent vs a showman? Never happen, but the planets aligned. Not because of him but because of unhappiness. Ironically, they still have that.