WTF Happened to Penn Jillette?!
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I think in his case it's worse than just TDS.
It's literally a physical deepfake. Magicians are painting a fake picture using tricks. To levy this criticism of Trump, to tie it to his profession, makes me think it's personal in that way.
In other words, Penn Jillette views Trump as a fellow performer who manipulates his audience and is better than Penn is. Like he's fine with Trump until they meet head-to-head, Trump looks like a boss, and Penn looks small.
He hosts a show where he essentially portrays himself as the best magician of all time. Occasionally they are "fooled", but not really; they're still the arbiters of magic, and being "fooled" is portrayed like tipping the hat.
It's envy.