A Second Look: The Flim Flam Brothers · 8:46pm Jan 13th, 2015
A surprising number of fans seems to be under the impression that Flim and Flam aren't really as villainous as the show attempts to portrays them. That they're just businessmen who brought some competition to Ponyville, that they technically won the contest for Sweet Apple Acres, and that these two Vaudeville inspired strangers who rode into Ponyville on their miraculous dream machine shouldn't be judged so harshly...
...okay, I'm exaggerating on that last bit, but the point is that people are enacting the old Draco in Leather Pants trope when it comes to a couple of charlatans.
The Super Cider Squeezy Six Thousand.
Most people seem to be under the impression that Flim and Flam produced this mechanical contraption themselves, but in their second appearance the SCSST is nowhere to be found. I'd propose that they either won or stole this marvel of automated apple-picking produce and lacked the ability to properly maintain it's inner workings.
Or the inner workings of the machine were so damaged by the trees, hunks of stone, and other various bits of refuge that got sucked up to make repairs more costly than it was worth. Which still shows a wanton disregard on the brothers part when it comes to their property's well being. How would they have treated Sweet Apple Acres when the choice between profit and the farm itself came up?
They'd have picked profit so fast your toupee would have spun.
Their Timing
Namely, how they show up just as the Apple Family have run out of cider. Again. It's indicated that this is a yearly issue due to the Apple Family's concern about quality over quantity. Plus their inability to put down a one mug per customer rule.
I'm looking at you, Miss Pinkamena Diane Pie.
Most people are used to characters showing up when they need to and how they need to for the sake of story. But my feeling is that Flim and Flam both choose to make their entrance at this point because it'd be when ponies were going to be pliable to the idea of quick, cheap, and plentiful cider. Which fits their manipulative personalities very well.
Winning the Contest
No, they did not win the contest. The vast majority of their produced product was undrinkable. They couldn't have given away those barrels, much less made a profit off them. Actually, if they'd dumped out the cider, cleaned them until the smell was gone, those barrels would have netted them a greater profit than what their overtaxed mockery of a Doctor Seuss creation had produced.
Thus, if you took away all their low-quality cider, those two lost by an enormous margin. Hence their Exit, Stage Left! reaction.
Conclusion
So, yeah, Flim and Flam are just as duplicitous as a pair of silver-tongued hucksters can get. They weren't lying, cheating, or stealing like more traditional bad guys. But their underhanded methods and monstrous arrogance make them bad people all the same.
Afterthought
Their next episode did in fact have them lying by claiming their snake oil could heal any ailment and hiring an assistant to fake said miraculous properties on stage, thus cheating all of those ponies out of their money, and running off with the profits before anyone could demand refunds...which I'd certainly call stealing.
I think the simplest way to sum it up might be to say that they were trying to run a scam in SSCSST, and accidentally failed to cheat. If they'd tried to conceal the rotten barrels underneath barrels of the earlier, higher-quality stuff, that would have had them living up to their names and natures.