Folks tend to talk about how Pippin addresses Denethor like they’re both equally ignorant of the political realities of the situation, but, like, Denethor probably knows exactly what the Shire’s political situation is? He’s looking at Pippin and in his head he’s like “okay, this provincial pipsqueak is being presumptuous as hell addressing me as a peer, but technically he’s within his right, and I can respect a power move” – and while Denethor is pondering how many levels of political power chess Pippin is playing here, Pippin is just *elevator music*.
pippin can also rely on “what are you going to do? check?” do you even have a map with the shire on it? if you sent a courier to investigate would he be able to cross goblin infested mountains, not get eaten by trolls, avoid the undead riddled burial grounds, penetrate a second semi-sentient angry forest containing a singing anomaly that may or may not be a demigod, and then find a race of people whose primary reaction to outsiders is to blend into the bushes, make it back again, and then be able to give you an answer other then admitting he was probably in the wrong place there were a lot of bear-men and not a damned person can give dirrections. heck, if you say you are looking for hobbits someone who knows what one is might even punch you because theyre a friend of bilbo and suspect you are a debt collector
Given that this sort of thing is in fact the basis of a whole family of time-honoured scams where one purports to be a nobleman from somewhere that’s too distant and obscure to readily verify one’s claims, the idea that Pippin was unwittingly pulling one of the classic grifts is funny as hell.