This puzzle is a homage to the early internet mystery game The Stone. Many of its riddles involved interpreting cryptic images, along with a lot of research, leading to some interesting finds. While they did often involve a lot of guesswork to get the exact answer, I dig the simple aesthetic and the knowledge of the world I gained.
Please excuse the semi-cruddy quality of the image. Paint will do that to you.
It would be good consider this image in three "sections". One section will give you who "he" is, and the other two will give you the "what". No ciphers (well, maybe in one small case) are necessary, just picture ID with a little word association thrown in.
The sections by the keys on the left or right lead to the "what". The three stacked pictures in the bottom center lead to "him". The gentlemen in the picture are related and held the same position, but "he" is neither of them.
The guys next to the SQUARE and OBELISK are a pair of politicians from the Northeastern US. One of them is currently serving. The "S" on the left is not just an S, but is normally seen as part of a corporate logo. As far as I can tell, "he" doesn't have any breathing problems...
I'll be happy to confirm individual bits if anyone needs it.