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It is possible to commit fraud in Pokémon Gold, Silver & Crystal, and Pokémon HeartGold & SoulSilver. My childhood vision of the Pokémon world being a crimeless utopia has been ruined and I've been feeling really weird and depressed about it since I figured it out a few weeks ago. The fact that there are people out there who used this tactic at some point in their playthroughs genuinely disgusts me. No self respecting Pokémon trainer would attempt commit fraud to further their career.
Let me explain how this all works.
By going to your mother and asking her to hold all of your money, you can go out and lose Pokémon battles, even important ones such as against Gym Leaders and the Elite Four, and you can just tell them you are broke, thus not having to pay the penalty for your loss.
This goes against the official Pokémon League rules, and is definitely a form of fraud, which you can actively partake in in the mentioned games.
To make things worse, your mother is complacent in this act, as your money isn't withdrawn from her balance when you lose a battle, suggesting that she isn't filing the losses.
There doesn't seem to be any prominent authorities to enforce the laws upheld by the Pokémon League in Pokémon Gold, Silver & Crystal, or Pokémon HeartGold & SoulSilver, but at the beginning of the game we did see a police officer assist with the case of the theft at Elm's Labratory. If you were caught commiting fraud, you and your mother would certainly get into a lot of trouble, especially if she was holding a large amount of money.
