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That one guy....

General Custer was an egomaniac who got his entire division, including my ancestor, killed at little big horn.  
Shame that so many good men had to die for his incompetence.
Background Pony #69D1
Custer was a Major General at the end of the Civil War. He reverted back to his non-brevet rank and was a Lieutenant Colonel at Little Bighorn.
 
Not sure why poor Rarity gets saddled with Custer. I’d peg her for JEB Stuart.
Background Pony #5A38
That picture isn’t from the Vicil War, it’s from the Indian Wars and that’s General Custer. You know, that guy that’s famous for having a last stand and all that jazz.
Background Pony #C7C5
@Trickquestion
 
There is no proof that dragons in MLP work like those in DnD. And do you really think the dragon would risk Fluttershy’s rage a second time? There are plenty of gems in Equestria, he could just fly over any old field and dig some up to replace the old ones.
 
Rarity was motivated by temporary greed. Custer was motivated by pride and ego which always had.
Trickquestion
The End wasn't The End - Found a new home after the great exodus of 2012

@Background Pony  
Let’s take a minute to examine the possible ramifications of her actions. Even if her theft had gone unnoticed and they succeded in convincing the dragon to leave peacefully, the dragon is going to take his hoard with him. He wouldn’t just leave all if it behind. That means he’s going to have to pack it all up and make several trips. Although dragon hoards are often disorganized, dragons have meticulous mental records of everything they hoard (now I freely admit I’m basing this off DnD, but both it and FiM are owned by Hasbro, and Friendship dragons do take a few cues from DnD ones). In the process of moving, he’ll notice what’s missing, put two and two together, come back to Ponyville to get his stuff back, and probably roast as many of those two-faced, double crossing quaprapeds as possible.
 
So yeah, it was a remarkably boneheaded move done entirely for personal gain and glory. One of the first bloody rules about dragons is never steal from one unless you plan on killing it first. The Custer comparison is apt.