Trump is all about hyperbole, broad generalisations and exaggerations. When he says a hundred people did x you can take it for granted, it wasn't a hundred people, maybe two or three dozen.
What does the press do, to discredit him, either deny his claim whole cloth or show what he was referring to. In the first instance they get shouted dozen as people show through social media and Conservative outlets, the dozens of people and they get slammed fot being fake news, or they show it was just the dozen people and he gets exposure on whatever he was talking about.
Its clever and it plays the press like a violin.
I think it is not entirely honest of him but it is not the worse kind of dishonesty. No secret billions in the dead of night to Iran, I never had sexual relations with that woman, I handed over all the emails kind of lying