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In 2015, Trump himself retweeted a picture of himself as a Pepe with the caption 'You Can't Win the Trump'

The picture has been deleted, but you can see in the comments that people are posting that exact image

There is also a article from 2016 about it posted by the BBC
Henry Martinez post about the shooter and it's blowing up, he also has a Pepe related PFP on his X profile
'You Can't Win the Trump' is a pretty ironic slogan after a attempted assassination