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Trump won because he actually listened to what voters were concerned about and addressed that in his platform.
For example, notice how he never said he would simply repeal Obamacare, he always said "we'll repeal it and replace it with something better." Because he talked to regular working class people and they said, hey, we DO like having coverage for pre-existing conditions.
Even though that's ideologically un-Republican of him, he still went for that because he listened to what people want.