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safe2174441 artist:artmarina-arts15 applejack200484 capper dapperpaws1805 rarity217550 abyssinian1598 cat8926 pony1602573 anthro359733 g42028959 my little pony: the movie21438 anthro with ponies3606 button1107 clothes634504 coat3955 comic135442 glowing horn29136 grin62982 horn190511 magic96630 meme93896 redemption148 scheming149 sewing688 smiling397464 stars23406 surprised12793 telekinesis39061 thought bubble5274 yaranaika313

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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
The Power of Love - Given to a publicly verified artist with an image under their artist’s tag that has reached 1000 upvotes
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Artist -

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?