Indeed it does. That far left side indicates that he will be addressing matters concerning personal will that influence something very visible in public. Being that the highest point is in Gemini, this probably will be about information.

Yes, that's the 12th usually. Pluto is not aspected other than favorably to both chiron and Neptune in Libra. This tends to mean that the subconscious won't have an issue using power on behalf of injustice. Often 12th house has to do with politics, and there is an indication of a spiritual wound here in injustice in specific that power will be applied toward. Being that Pluto is in Leo, it tends to mean the ego is going to use the power well or demonstrate how properly used power should look.

The other story is the Mars there, but it's almost in the 1st and might as well be there. This directly concerns identity and the fight that needs to be fought. There is more to be said here in relation to the fact that the moon was in an eclipse the day Trump was born, so blood is directly related to this narrative, and Mars tends to rule blood. Putting the two together you might get something like "purging the blood of the subconscious" or mass mind.

So the interesting thing concerning philosophy is tied to the childhood home there in the fourth house which is Sagittarius. It means that where he goes to nurture himself is a specific kind of faith, but the South node is there, meaning being in your home and shy is something he's leaving behind or going to tend to want to leave behind. Jupiter rules Sagittarius, and so large homes near the water would be possible--or large homes in the desert depending on the philosophy.

The career is in tension with the home, but it is where the soul urge is. The soul urge is in Gemini, which concerns knowledge or possibly the word "harvest" in a public light that is the "knowing" of the faith informing the root. This top part of the chart is yang, typically, and the bottom is yin, typically, and the massive tensions here are probably unpleasant as the public and private lives are going to be pulled in opposite directions. The soul, however, puts one out for people to see, and places with communication or television are usual haunts for a Gemini. Occasionally you see it with colleges in this placement.

The green line to Mars in the first/twelfth house means that the emotions are going to fight on behalf of things that are probably not seen by everyone and usually the 12th house indicates politics and indeed, politically he is known as a fighter.

That Mars aspect makes less great contact to the Taurus in the 10th at the MC, and often times with a lot of Taurus like this in a chart you will see vocal performers. Pavarotti, for instance, had a load of Taurus up in this house. Trump tends to play his music, but in this case the Taurus conservation has kicked in.

It's interesting because that first house contact says the ego isn't really wanting to identify inherently as a conservative. Indeed, an "old school Democrat" might appeal more to the egoistic expression, but it doesn't matter as Taurus comes in and says what must be kept for the sake of the public.

Lots of tension here between the home, philosophy, public, and identity.

Red lines are oppositions and squares, which form tension in a chart. Green are trines and I think sextiles in this one, which are smooth aspects.

That's not really a question.