It means you are aligned with what the media wanted you to believe about him for the past 4 years: That he is incompetent, that he is unorganized, that he is impulsive, that is is stupid, that he is careless, that he is nearsighted, that he is greedy, that he only looks out for himself, that he is incapable, that he is doomed for failure.
In other words, if you are doubting President Trump right now, then .win isn't a place for you.
He will never run for president He will never get the nomination He will never beat Hillary He will be found guilty of collusion with Russia He will never get a second term