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DockWater

@SourCherry  
Or just by being a better con-artist. Sure, he’s only fooled the townsfolk of Gravity Falls, who aren’t the brightest people in the world, but he has a perfect record of fooling them where the Flim-Flam brothers have failed to fool the citizens of Ponyville, who are just as stupid as the townsfolk of Gravity Falls if not stupider.
AlchemyGold
The End wasn't The End - Found a new home after the great exodus of 2012

If these are the pre-mark Crusaders, I can see Stan offering to “help” them get cutie marks in taxidermy, counterfeiting, cleaning the portable toilets, and whatever needs doing around the Mystery Shack.
SourCherry
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
The Power of Love - Given to a publicly verified artist with an image under their artist’s tag that has reached 1000 upvotes
Best Artist - Providing quality, Derpibooru-exclusive artwork
An Artist Who Rocks - 100+ images under their artist tag
A Really Classy Artist - 250+ images under their artist tag
Artist -

I imagine that seeing Grunkle Stan meet the Flim Flam brothers would be rather… interesting. Filled with so many cons, proclaiming some form of friendship while taking money out of each’s pockets.  
…  
…  
Stan would win in the end, if only by sheer brute force of fist to the face, run with the money :P