I think it's a technically good and accomplished photo. Possibly the photographer was aiming to capture Trump's stubbornness, determination, and power- e.g. others looking up to him... The disappearing small bit of his hair possibly to look like some kind of halo?
The angle of the photo though highlights his age, weight, and loose skin on his neck- but it is true to life. The trouble is Trump doesn't see himself how he actually is so any photo that captures his actual image, without filter, he no will not like.
He likes to be on the cover of TIME though for all the world to see- so he shows his narcism and thin skin by calling it "super bad" highlighting image is more important to him than substance.