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Water and Psychic are the only types where you can fight a specialist of it in every single Pokémon game outside of Legends Arceus. For Water, Misty can be fought in all the Kanto and Johto games, Wallace and Juan in the Hoenn games (with Juan being Emerald only), Crasher Wake in the Sinnoh games, Cress in BW1, Marlon in BW2 (along with Misty, Wallace, Juan, Crasher Wake, and Cress all returning for the PWT), Siebold in XY, Lana in the Alola games, Nessa in Sword and Shield, and Kofu in Scarlet and Violet. For Psychic, there's Sabrina in the Kanto and Johto games, Will in the Johto games, Tate and Liza in the Hoenn games, Lucian in the Sinnoh games, Caitlin in the Unova games (along with Sabrina, Tate, and Liza returning as PWT entrants), Olympia in XY, Faba and Dexio in the Alola games, Bede (initially) in Sword and Shield, and Tulip in Scarlet and Violet. Fighting came close, with it only missing Shield due to Bea being a Sword exclusive character.
Jasmine's backstory is reflected in her signature Pokémon, Steelix. Steelix's pre-evo, Onix, is a Rock type before losing that type upon evolution in favor of Steel. The same is true for Jasmine herself, who is stated in game to have originally been a Rock-type specialist before switching to Steel upon its discovery.
In the Sinnoh games the game will crash if you lose the initial battle against Starly upon receiving your starter. Normally the Starly will flee if your HP gets too low, but your starter can faint, but it requires a very specific setup.
In Gen 3 competitive, it is illegal to use a Wobbuffet holding Leftovers. This is because a battle between two Wobbuffet holding Leftovers will not end in Gen 3, as the Leftovers will heal back more HP than it loses from Struggle, it can only deal direct damage by counter-attacking with Counter and Mirror Coat, and its ability Shadow Tag prevents any Pokémon on the field from switching out. In Gen 4, this issue was fixed by making Shadow Tag have no effect if another Pokémon with the ability Shadow Tag is on the field.
The Sweet Honey mechanic featured in DP was originally supposed to be in GS, according to unused text. More unused text also implies that the Pharmacy was originally going to be in Ecruteak, but it was moved to Cianwood in the final game.
Ghost is the only type to have its matchups modified twice. In GS it became super effective against Psychic (Psychic was immune to Ghost in Gen 1 due to an oversight) and in XY Steel lost its resistance to it.
Jasmine's backstory is reflected in her signature Pokémon, Steelix. Steelix's pre-evo, Onix, is a Rock type before losing that type upon evolution in favor of Steel. The same is true for Jasmine herself, who is stated in game to have originally been a Rock-type specialist before switching to Steel upon its discovery.
In the Sinnoh games the game will crash if you lose the initial battle against Starly upon receiving your starter. Normally the Starly will flee if your HP gets too low, but your starter can faint, but it requires a very specific setup.
In Gen 3 competitive, it is illegal to use a Wobbuffet holding Leftovers. This is because a battle between two Wobbuffet holding Leftovers will not end in Gen 3, as the Leftovers will heal back more HP than it loses from Struggle, it can only deal direct damage by counter-attacking with Counter and Mirror Coat, and its ability Shadow Tag prevents any Pokémon on the field from switching out. In Gen 4, this issue was fixed by making Shadow Tag have no effect if another Pokémon with the ability Shadow Tag is on the field.
The Sweet Honey mechanic featured in DP was originally supposed to be in GS, according to unused text. More unused text also implies that the Pharmacy was originally going to be in Ecruteak, but it was moved to Cianwood in the final game.
Ghost is the only type to have its matchups modified twice. In GS it became super effective against Psychic (Psychic was immune to Ghost in Gen 1 due to an oversight) and in XY Steel lost its resistance to it.