Apparently 3 people can’t admit George Clooney isn’t wearing that shirt to say they’re “losers”, he’s wearing it to say they’re evil, and stupid enough that they’re doomed to lose because they are ignorant of actual history.

Would he be wearing it if he agreed with the people being criticized? Like if he thought that it was, say, women, with the "losing" topic being anti-women legislation, he would probably not wear it. He wears it because he thinks that these people who are losing are also morally reprehensible. And, of course, that they are "losers" as well. But I don't think that saying that "he wears it to say they're evil" is complete falsehood, although the message is probably more like "these people are evil but they lose every time".