He is the first US president (including George Washington) to never have worked for the government in any capacity prior to being elected president. He's more of an "outsider" to the bureaucracy than anyone has ever been.
I am not so sure. If Trump had the calm personality of #43 who never fought back, or had the smooth delivery of #40 who also rarely got in the face of media, or was the first black president #44 with liberal tendencies and also never fought with media, the media wouldn’t care less if Trump was from Mars. They are annoyed because he insults them back immediately when they insult him. It has not happened in my observation since I immigrated in 1960.