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safe2233967 artist:artmarina-arts15 applejack205378 capper dapperpaws1823 rarity222798 abyssinian1642 cat9309 pony1664068 anthro374538 g42096244 my little pony: the movie21587 anthro with ponies3720 button1160 clothes662042 coat4123 comic138759 glowing horn30407 grin65800 horn223681 magic99947 meme95848 redemption172 scheming155 sewing708 smiling420728 stars24842 surprised13296 telekinesis40596 thought bubble5724 yaranaika314

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Background Pony #F357
The prequel story gives much more insight into his character. Not to mention how he got in debt in the first place.
toonbat
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What made this specially odd… well, it’s a bit hard to explain, but I’ll try.
 
a) he was baffled to find out that the ponies were actually nice.
 
b) yet if he didn’t expect the ponies to be nice, why fashion himself to be a nice guy? You usually try to con somone by speaking their language and catering to their expectations. If he had thought the ponies were greedy and selfish, wouldn’t it have made more sense to play off as a shady businessman offering a sweet deal?
 
So yeah, to me it seems that if he played himself off as saintly, it’s because that is what he expected the ponies to accept. And the only reason they would have believed it, would be because it met their expectations. As in, they were used the idea of people being actually decent.
 
So why would he be so surprised by them actually being decent themselves? Isn’t that what he read them out to be in the first place? Isn’t that why he played that part to woo them?