Grass is the third most common type in the Pokémon franchise. As one-third of the Starters in each generation, Grass holds a privileged place in every region of the Pokémon world. Players also find certain Grass-type Pokémon at the beginning of every journey in the early routes of the games. In the end, most players will likely have at least one Grass-type on their team.
Because of its prevalence in the Pokémon world, several trainers in the games are Grass-type specialists. They are usually Gym Leaders; to this day, no Elite Four member specializes in the type. And while Grass has a lot of weaknesses, defeating some of these specialists is more challenging than it might seem.
6 Milo
Sweet and unassuming, Milo is not the best trainer in Galar. In fact, it's common knowledge that he usually has trouble giving it his all with weaker trainers. Milo loves Pokémon battling, and so his primary focus is to enjoy himself. Hence, he's Galar's first Gym Leader because he poses no real challenge. He lives in Turffield and gives the Grass Badge to players who manage to defeat him.
His team includes only two Pokémon of the same family. Both are pure Grass-type, which means they have five weaknesses. Players without Scorbunny on their team can still get by using either the Flying-type Rookidee or the Rock/Fire-type Carkol.
5 Cilan
Like Milo, Cilan is the first Gym Leader in the Unova games. He runs the Striaton Gym with his two brothers, Chili and Cress, and they give the Trio Badge to players who manage to defeat them. However, players only battle him if they have Oshawott as a starter, making Cilan's Pansage super effective against the player's strongest Pokémon. Cilan also has a Lillipup that's more a nuisance than an actual threat.
At that point in the Unova games, players will likely only have their starter and either a Lillipup, Patrat, or Purlloin, caught in Routes 1 or 2. None of these Pokémon have type advantages against Cilan's two mons, making the battle slightly more challenging.
4 Ramos
The Kalos games are infamous for how easy they are. Every Gym Leader is basically a walk in the park, and Ramos is no exception. He is the fourth Gym Leader in the Kalos League and gives the Plant Badge to players who defeat him. Ramos only has three Pokémon, two of which don't even have full movesets. His Jumpluff knows Acrobatics and is very fast, which might be problematic.
His strongest mon, Gogoat, is a pure Grass-type with Bulldoze to counter Fire-types, which might seem like a good strategy. However, most players would have Talonflame on their teams, and its Flying-type makes it immune to Ground moves, making this Gym battle even easier.
3 Gardenia
Gardenia is Sinnoh's second Gym Leader, who gives the Forest Badge to players who defeat her. She lives in Eterna City and has a team of three Pokémon, each stronger than they seem. She will use Turtwig to set up Reflect. For some reason, Turtwig also knows Sunny Day, which is odd considering none of her Pokémon know Solar Beam or Weather Ball.
Cherrim is there just to stall and serves as an opening act for Gardernia's signature Pokémon, Roserade. It knows Magical Leaf, a move that always goes first. Its Poison Sting and Stun Spores can also be problematic, particularly if the former poisons the player's Pokémon.
2 Mallow
Unlike her anime counterpart, Mallow doesn't play a prominent role in the Generation VII games. She only appears briefly as the Trial Captain of Akala Island's Lush Jungle. Her main team consists of only three Pokémon. They are pre-evolved in the original Sun & Moon, but not in Ultra Sun & Ultra Moon.
Her team in US&UM is quite decent. It could be better, but Shiinotic brings them down. It's just not a very good Pokémon, thanks to its mediocre stats. That leaves Trevenant and Tsareena as her only worthy Pokémon. What brings these two down is that they only know three moves, none of which is super effective or even useful against Fire-types.
1 Erika
Genwunners will say Erika is the best Grass-type specialist, and they might have a point; her team is stronger and more well-rounded, though only because players fight her in the mid-stages of the game instead of at the beginning. Canonically, she is the fourth Gym Leader, found in Kanto's largest city, Celadon. She gives the Rainbow Badge to players who defeat her.
Erika's team is the same throughout her many appearances in the games. Her Tangela is completely useless and mostly there just to stall. Victreebel's Poison moves can complicate things if they poison the player's Pokémon. Her ace is always Vileplume, who almost always has three Grass moves and one that's Poison-type.
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