It goes back to trans athletes. The dude makes shit up, but what it comes down to is that he's saying biologically female weight lifters can't compete with trans weight lifters, and so let's just hate them. Everything he does is fueled by hate, it really doesn't matter what the specifics are.

He explained it in the video. He said she doesn't like him doing the impersonations because its not presidential. She's a horrible person too, but she understands that her dotard husband is just an absolute bufoon on the world stage

The photo is him reliving the event when he was the cream in the oreo in between Putin and Kim Jong Un