WTF Happened to Penn Jillette?!
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Textbook TDS. Comparing 2015 and earlier Penn and post 2016 Penn and it's radically different. He said he had some negative issues with Trump when Trump was hosting The Apprentice (which may be legitimately true) but then translated that into full-on Orange Man Bad. Even then, he still called himself a Libertarian up until The Coof, at which point he went full-on pro-lockdown and pro-mandate and has continued sliding.
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.