I heard that too about Dingle. He was talking about when he called her after her husband’s death and she was happy and appreciative. Trump was relating that call at the rally and said “she said he is looking down and smiling I know”(about the call) President said, well he might be looking up(referring that her husband might be in hell).
He says these things out of no where. Not sure why he brought up Dingle and his wife at the rally.
non religious or non studying religious people many times don’t see a difference in meaning between heaven and hell.. preferring to think there is no such thing as hell. So up or down would be the same as, or no difference.