Gym Leaders are a staple of most Pokémon games. Serving as the series’ bosses, Gym Leaders act as gatekeepers to ensure players understand type matchups, and train a balanced team. Gym Leaders also give out key items that players need to progress.
Because most Gym Leaders specialize in a single type, they can often be defeated by simply exploiting type advantages. However, some are infamous for giving even experienced players trouble. Whether it’s due to their placement in the game, strong Pokémon builds, or other factors, these Gym Leaders often become major roadblocks on the path to victory.
10 Blue Is a Rival Turned Gym Leader
Appears in Pokémon Gold, Silver, Crystal, HeartGold, and SoulSilver
One of the best features of the Johto games and their remakes is the ability to explore all of Kanto and challenge its Gym Leaders, with the exception of Giovanni. In his place, former rival Blue has taken over the Viridian City Gym, and while it might be easy to cruise through the other Kanto Leaders, Blue is likely to stop that momentum cold.
Fittingly for a former champion, Blue uses a high-level, type-diverse team with solid movesets and held items. Any trainer expecting to sweep through with simple type advantages is in for a surprise. Still, by this stage in the game, the player is no pushover either. While Blue might catch some off guard, it doesn’t take long to regroup and take him on properly once his strategy is clear.
9 Raihan Is One of Pokémon's Toughest Late-Game Gym Leaders
Appears in Pokémon Sword and Shield
For the most part, late-game Gym Leaders are easier than early ones, simply because players have stronger Pokémon and better movesets by that point. This holds true in both older titles and newer games, which tend to be easier overall. Sword & Shield, however, subverts this trend with its final Gym Leader, Raihan. Although he’s technically a Dragon-type specialist, Raihan functions more like a weather specialist and challenges players to a double battle. Most serious singles teams struggle when forced into doubles, and the same applies in reverse, making this sudden shift in battle format a real test.
Raihan enters the battle with a solid sandstorm team, complete with synergy and strategy that can catch players off guard. Those unprepared for the shift from singles to doubles can easily find themselves overwhelmed. While Raihan might come as a surprise at first, the battle is manageable with a bit of adjustment on the second attempt. Still, considering how easy recent Pokémon games tend to be, Raihan stands out as a rare late-game challenge capable of tripping up unprepared trainers.
8 Clair Proves That Dragon Gym Leaders Are Seriously Tough
Appears in Pokémon Gold, Silver, Crystal, HeartGold, and SoulSilver
Dragon-types in the first two generations are difficult to deal with because they’re only weak to other Dragon-types or Ice-types, and they resist many common types. This makes Clair a tough battle. Only two Dragon-type Pokémon are available to players in the Johto games: Kingdra and the Dratini line. Kingdra requires a trade evolution, making it inaccessible without a Link Cable, while Dratini has only a 10% encounter rate via fishing outside of Blackthorn, assuming the player remembered to get the Good Rod.
Ice-type Pokémon are more readily available, but they don’t help much against Clair’s Kingdra, which can paralyze with Dragon Breath, lower accuracy with Smoke Screen, and hit hard with Hyper Beam and Surf. In HeartGold and SoulSilver, the difficulty of obtaining a Dragon-type remains, though there are slightly better Ice-type options. Clair also swaps out one of her Dragonair for a Gyarados, which presents its own set of problems, even if Kingdra no longer carries Hyper Beam and Dragon Breath. Johto’s level curve can be uneven, but Clair stands out as a major challenge before reaching the League.
7 Fantina Is Seriously Challenging in Pokémon Platinum
Appears in Pokémon Diamond, Pearl, Platinum, Brilliant Diamond, and Shining Pearl
Fantina is a tough opponent when faced as the fifth Gym Leader in Pokémon Diamond and Pearl, but in Platinum, where Fantina is battled third, she becomes a major roadblock. Ghost is already a tricky type to counter, being weak only to itself and Dark-types, and the only Dark-type available without trading is Stunky. All three of her Pokémon carry moves that inflict status conditions, with Haunter using both Confuse Ray and Hypnosis to disrupt battle flow.
Her ace, Mismagius, is especially difficult to handle. As a strong Special Attacker, it can deal heavy damage with Psybeam or Magical Leaf, confuse opponents with Confuse Ray, and potentially lower Special Defense with Shadow Ball. On top of that, it holds a Sitrus Berry to recover health mid-battle. Platinum throws this already difficult fight at players at a point when counter options are still limited, making Fantina one of the game’s most punishing early challenges.
6 Juan Is a Tougher Gym Leader Than Wallace
Appears in Pokémon Emerald
Juan is only battled in Pokémon Emerald, replacing Wallace, who has taken on the role of Champion, so some players might be surprised by how frustrating his team can be. It’s not that the rest of his Water-type team is especially difficult to handle; the real challenge comes from his ace, Kingdra, echoing Clair’s strategy from Gold, Silver, and Crystal. As before, Kingdra’s typing makes it difficult to counter, though at least more Dragon-types are available in this game.
Several factors make Juan’s Kingdra even more irritating. First, it replaces Smoke Screen with Double Team, meaning switching out no longer helps with evasion issues. Second, it carries Rest and a Chesto Berry, allowing it to fully heal and immediately wake up on the same turn, if it can even be hit while asleep, thanks to all the evasion boosts. Its attacking moves, Water Pulse and Ice Beam, both carry secondary effects that can confuse or freeze. Juan’s Kingdra is built to be as difficult to hit as possible, with strong recovery options and status-inflicting attacks, not to mention the added pressure of Juan’s own healing items.
5 Elesa Challenges Players With Two Emolga
Appears in Pokémon Black, White, Black 2, and White 2
Elesa’s pair of Emolga in her first appearance may be adorable, but they’re absolute menaces to deal with. Both are immune to Ground-type moves, which are typically the best counter to Electric-types, and can outspeed and chip away at the player’s team with Aerial Ace or Quick Attack. Each one also uses Volt Switch to deal damage and retreat before being hit, and both have the ability Static, meaning any Physical move used against them runs the risk of paralysis, making it even harder to outspeed them in return.
Then there’s her Zebstrika, which hits hard, especially against a team already weakened by Volt Switch. It also carries Flame Charge to cover for Grass-types brought in to resist Electric moves. While this challenge is made a bit more manageable by the availability of a Sandile on the route before Nimbasa City and access to the TM for Rock Tomb, the appeal of Pokémon lies in beating battles with a personal team, not being forced to catch a specific counter. Fortunately, Elesa is easier the second time around in Black 2 and White 2, which may speak to just how tough her original battle was.
4 Norman Is the Father of a Pokémon Protagonist
Appears in Pokémon Ruby, Sapphire, Emerald, Omega Ruby, and Alpha Sapphire
It’s fair that, as the player’s father, Norman wouldn’t want to hold back, but there’s no reason for him to be this tough. His ace is Slaking, a Pokémon with incredibly high stats, balanced only by the ability Truant, which forces it to skip every other turn. That’s manageable with prior knowledge, but depending on the game, Norman’s team comes with tricks designed to work around that drawback.
In Ruby and Sapphire, Norman’s team isn’t that tricky to deal with, though both of his first two Pokémon know Encore, which can be frustrating if it locks a key team member into the wrong move. In Emerald, his Slaking gains access to Counter, punishing reckless physical attacks with double the damage. Still, once Truant is understood, the battle becomes easier to manage. The real challenge appears in Omega Ruby and Alpha Sapphire, where both of Norman’s Slaking know Retaliate, a move that doubles to 140 base power if a teammate fainted on the previous turn. Most Pokémon available by that point in the game can’t survive a hit that strong from a Slaking, especially not after losing another team member.
3 Whitney's Miltank Is a Menace
Appears in Pokémon Gold, Silver, HeartGold, SoulSilver
Whitney is designed to roll every annoying Gym Leader strategy into one of the most infamous battles in the series. It takes place early enough in the game that the player has limited counter options, while her Miltank boasts stats far higher than most of the non-fully evolved Pokémon available without grinding. Miltank also has multiple ways to immobilize opponents, like using Attract on male Pokémon or causing flinches with Stomp, and often outspeeds other Pokémon due to its unusually high stats for this stage in the game.
On top of all that, Miltank can heal itself with Milk Drink, dragging the battle out even longer. It’s a recipe for frustration, and the developers seemed to anticipate that, as they provide a free counter to Miltank. By catching a Drowzee just outside Goldenrod, players can trade it at the Department Store for a female Machop, a solid option to handle Whitney’s toughest Pokémon.
2 Lenora Shows That Normal-Type Pokémon Can Be a Serious Threat
Appears in Pokémon Black and White
Lenora falls into the category of Gym Leaders made more difficult by the player’s lack of options, though she has enough tricks to be tough regardless. As the second Gym Leader in Black and White, Lenora’s Herdier and Watchog are a brutal combo for early-game teams. Both know Leer to lower Defense and are surprisingly fast for this stage, allowing them to set up damage quickly.
Anyone trying to brute-force through the fight with Pignite can expect to be softened up by Herdier’s Leer before taking a devastating Retaliate from Watchog. Watchog also carries Hypnosis, which can either ruin a run entirely or just be incredibly disruptive. After facing Lenora, players tend to think twice before underestimating the Normal-type.
1 Sabrina
Appears in Pokémon Red, Blue, Yellow, FireRed, and LeafGreen
Sabrina gave Ash his toughest battle ever, and she’s just as challenging in the games. She’s Pokémon‘s hardest Gym Leader for one very simple reason: Psychic was broken in Kanto in a way no other type has been before or since. This was especially true in the original Gen I games. There were no Dark-type Pokémon in Gen 1, so Psychic’s only weaknesses were Bug and Ghost, but Bug-type moves were weak across the board, and due to a glitch, Psychic-types were immune to Ghost-type attacks instead of being weak to them. On top of that, Special Attack and Special Defense were combined into one stat, giving Pokémon like Alakazam both offensive power and surprising durability.
Even in FireRed and LeafGreen, the Sabrina fight remains difficult. While the Dark-type exists, no Dark-type Pokémon are available until the post-game, as they’re not in the Kanto Dex. Bug-type moves are still underpowered, leaving the Gastly line as the only real option for super-effective damage. The problem there is that Gengar is a trade evolution, making it inaccessible without another system, and the entire line is part Poison-type, making them weak to Psychic. It isn’t until Let’s Go Pikachu and Eevee that the odds start to even out, with access to Dark-type Alolan forms and Alolan Marowak as a stronger Ghost-type alternative. For years, Sabrina has remained one of the series’ biggest challenges due to a sheer lack of viable counters.
