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safe2198722 artist:artmarina-arts15 applejack202497 capper dapperpaws1814 rarity219596 abyssinian1604 cat9066 pony1629232 anthro365624 g42054982 my little pony: the movie21510 anthro with ponies3657 button1131 clothes645220 coat4036 comic136891 glowing horn29562 grin64034 horn204331 magic98008 meme94649 redemption155 scheming153 sewing699 smiling406230 stars23927 surprised12987 telekinesis39663 thought bubble5455 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?