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In the case of a US president that's highly suspicious, but a replaceable moderate pundit is far from a high value target so it's reasonable for security to be more lax and things that seem off to be overlooked.

Honestly I struggle to find any political figure who was as well known as him who had a more dispassionate reception in this polarized climate. Seriously he's like one of the first people I'd think of as an example of someone who is known but irrelevant.