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As stated above, Moneybags first appers in Avalar meaning he first appered in Spyro 2: Ripto's Rage. He wastes no time ripping Spyro off from the very first level in the game, where he will extend a bridge to the end of the level only if he pays him 100 of his hard earned gems. From then on he continues to take Spyro's gems in various levels for various reasons, such as unlocking new levels or borrowing his submarine in an aquatic level. However, in the end, Spyro gets everything back when he defeats Ripto. He refuses to give Spyro his money back after he pretty much earned it, so Hunter beats him up and retrieves the lost treasure.
In the third game Year of the Dragon, he makes his return. His role doesn't change from the greedy bear who loves gems. As such he will continue to take Spyro's gems in exchange for his "services". However, Spyro does get his gems back (again), only this time, Spyro personally sees to the return of his gems.