What is this in reference to? I am out of the loop.

There's no loop. I really wanted to make a Elon/Bibi joke but there were only a few photos to work with. I cropped the photo and I realized their expressions seemed perfectly creepy and a great match to the headline I already wrote.

Also, wtf is this lunatic talking about?

I have no idea but my wild hunch it's nothing in particular. He saw a chance to jump into a Elon tweet-related thread about the typical use of Chicago as a racist euphemism for black people. People like him want to be racist but they also desperately want likes and mainstream engagement too.