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.
Or maybe we are objective and don't follow false flags? How is it about doubting or not, if you don't doubt all the things you see you are not better than a 5 year old believer in Santa. Any statements about how "strong" we should be belongs to regimes like North Korea.