On the care and feeding of confidence tricksters. · 10:35am Aug 10th, 2018
Without actually probably intending to, the writers are starting to do the viewers something of a service by putting Flim and Flam in charge of the alternative friendship school Neighsayer is running. This is because they've shone a light on a dynamic that people need reminding of: the one between a con man and his willing mark.
As we know, what makes a con man tick is his inability to really understand any sort of mutually beneficial relationship. The linchpin of our free market system of economics is that both sides stand to gain from a business deal but the con man, he can't wrap his head around that. What he sees is himself as the victor to be praised and his mark as the loser to be scorned. He is thus a danger because he leaves behind him all amount of wreckage that he feels no responsibility for. It's why they didn't wanna do things honest in Las Pegasus; they couldn't because they don't see their lives as being wrong.
The reason that they prosper is rather sadly simple: there seems to be an almost endless array of people who seem to want to be cheated and the means of doing so is for the con man to identify a crippling character flaw that the mark foolishly sees as a strength. When they tried to cheat the Apples, they found a group of willing suckers with a metric ton of pride to exploit. With Neighsayer, it's the need he has of being proven right no matter what the cost. He'd burn down Equestria and start a war so he could 'prove' that Twilight was reckless and naive, you see.