Pre-presidency: When he went on the Colbert Report for a segment about wanting to fly a cartoonishly large American flag at one of his golf courses but then had to admit that he didn't know what the 13 stripes represented. https://twitter.com/kept_simple/status/1351982539813097474
During his presidency:
Other examples: Any of the times he claimed to have invented terms or coined phrases ("fake news," "priming the pump"), Boy Scout rally rant about sex on boats, when he said he tested positive for COVID before realizing that positive was bad so said "positively towards negative"
This moment
Oh, and then the time he had a fake movie trailer made where he and Kim Jong-un were action heroes
Or when White House staffers couldn't get him to stop shredding documents he was legally obligated to save, so they had a guy going around trying to tape them back together https://www.politico.com/story/2018/06/10/trump-papers-filing-system-635164
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