He knew he was being surveilled and “fed” them bad intel by means of that surveillance, which is hilarious to the point of utter humiliation for Obama, Hilary Clinton, the “intelligence community” such as it is and the political left as a whole. They’re willing to bring it all down in order to avoid that coming to light. They got played due to their own heavy-handedness.
I even considered an outlandish scene where Donald Trump was on the phone arguing with someone on his campaign leadership team, yelling something along these lines: "Why are you sending me to Wisconsin again? Hillary's going to kick my ass there?!" LOL.