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Champions of Equestria

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safe2289080 artist:artmarina-arts15 applejack209208 capper dapperpaws1850 rarity226782 abyssinian1686 cat9652 pony1719007 anthro379927 g42130090 my little pony: the movie21679 anthro with ponies3872 button1201 clothes682586 coat4324 comic142709 glowing horn31622 grin67718 horn256006 magic103406 meme97575 redemption182 scheming155 sewing727 smiling434098 stars25774 surprised13682 telekinesis42043 thought bubble6119 yaranaika318

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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?