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Generation 3 of course. Strategically the types aligned well with their placement and they had their own battle styles.
>brawly
Offensive fighting type pokemon early on thats neutral to all starters
>flannery
overheat overheat overheat
>norman
offensive defensive trainer that made best use of normal types
>tate and liza
first use of double battle with optimal pokemon for its generation
>wallace/juan
Ideal last gym leader place to take advantage of powered up water types