10. Brock
It’s a bit weird to say that Brock is one of the toughest Gym Leaders since he’s the first Gym battle in the very first Pokemon games. But depending on which starter you choose, those Rock/Ground-types can absolutely crush you.
Good luck to all the Charmander owners in the original Red and Blue because that Pokemon is not budging Brock’s Geodude, Onix, and his five Full Heals. You could catch a Caterpie or Nidoran and grind to level up high enough to overcome the challenge, but that would take forever against the low-level Pokemon found just before his Pewter City Gym.
The far easier solution here is to pick Squirtle or Bulbasaur in the original games. To those who stuck it out and persevered, I salute you and your soon-to-be Charizard for your bravery.
9. Falkner
Falkner is another Gym Leader that you wouldn’t expect a challenge from, as he’s the leader of the first Gym in Gold, Silver, and Crystal. However, the tricky part about his team is that it’s Flying-type, which doesn’t offer up any advantages for the starters, and is a bad matchup for Chikorita.
Things get even trickier when you realize his Pidgey and Pidgeotto both know Mud-Slap — a Ground-type move that’s super effective against Cyndaquil and the Onix you can obtain before the Gym.
The move also lowers accuracy, so this fight has the potential to be much more challenging than it has any right to be for one that happens so early on.
8. Wallace
Wallace is a Water-type Gym Leader in games that are absolutely full of Water-type Pokemon. He also has certain Pokemon that completely negate the Grass and Electric-type weaknesses. He comes late in the game, but he’s ready for you.
Even if you do have a Grass-type to take him on, his Milotic and Sealeo both know Ice-type moves to retaliate with, so you better not mess up. Milotic’s Ice Beam and Whiscash’s Earthquake, in particular, are nothing to mess around with.
To top things off, every single one of Wallace’s five Pokemon knows Water Pulse, which has a chance to confuse if it hits.
7. Elesa
Elesa is the fourth Gym Leader in Pokemon Black and White, and her setup is just plain annoying. Her two Emolgas along with her Zebstrika can cause a lot of problems for those who think they can just walk in with Ground-types for the win.
All three starters will be at a type disadvantage when going up against Emolga at this point in the game, so it’s up to the rest of your other Pokemon to pull through against one of the most problematic Gym Leaders in Gen V. Unfortunately, Emolga is only weak to Rock and Ice-type moves.
As if the type disadvantages here weren’t enough, the two Emolgas have the Static ability, which can potentially paralyze your physical attackers. And all three of her Pokemon know Quick Attack and Volt Switch, making this a game of electric hide-and-seek at times.
6. Winona
Winona’s Flying-type Gym comes right after another tough battle against Norman in Ruby and Sapphire, and she’s got something to counter each of the Gen III starters. Both Treecko and Torchic’s evolution lines are weak to Winona’s Pokemon, and Mudkip’s line can’t use any Water or Ground-type attacks that would be of use here.
Her Pelipper covers its Rock-type weakness while her Skarmory and Altaria negate the Electric-type weakness. Rock and Ice moves are your best bets here, but even that can be dangerous if they’re actually coming from Rock and Ice-Type Pokemon.
Even if you have all of the right typings to put up a fight, Winona’s Altaria is a problem. Its move set of Dragon Dance, Earthquake, Aerial Ace, and Dragon Breath can easily poke some holes in an ill-prepared team. Let her get off enough Dragon Dances, and you’ll be saying goodbye to a few party members when the Earthquakes start coming.
5. Norman
In Ruby and Sapphire, Norman will absolutely bully you with his two Slakings and Vigoroth. Those sloth/ape hybrids will just sit there while you do your very best to whittle down their health. As they take those hits, one will heal with Slack Off, the other will put you to sleep with Yawn, and both can force you to use moves that you don’t want to with Encore.
The Slakings have a lot of HP and high defenses, so poison might be a good idea, right? Well…maybe. They, along with the Vigoroth, also have the move Facade, which boosts attack when the Pokemon is under certain status conditions.
Depending on your party setup, you’ll be in this one for the long haul. Of course, this fight is a little easier with Combusken or Blaziken, but even with a type advantage, Norman also has two Hyper Potions to use whenever he feels like it. Norman is the last of the Hoenn Gym Leaders on this list, but that Pokemon Generation really made you work for your badges.
4. Clair
Before she started cheating with her Gyarados in HeartGold and SoulSilver, Clair defended her Dragon-type Gym with a team of three Dragonairs and a Kingdra in Gold, Silver, and Crystal.
There aren’t a lot of options to fight that team within Gen II, but thankfully, Pryce gives you an Ice-type TM before you have to go head-to-head with Clair. It’ll help with her Dragonairs, for sure, but the Water/Dragon-type Kingdra will brush it off easily.
This battle really makes you realize that Fairy-type was a godsend because Kingdra was only weak to Dragon-type moves at the time, and every Pokemon on Clair’s team can use Dragon Breath to counter any dragon you bring along while also paralyzing the rest of your team. The Dragonairs all know Thunder Wave for more paralyzation potential, and one even knows Ice Beam, just for good measure.
3. Whitney
We probably all knew Whitney would be mentioned on this list eventually. Some of us still have nightmares about her Miltank, but it’s okay — we’ve made it to Gen VIII and she can’t hurt us anymore.
But man, did she stonewall most teams in Gen II. That Miltank can really take a hit (or several) and it makes Whitney one of the toughest Gym Leaders in Pokemon. Her Clefairy’s Encore is more annoying than worrying, but her Miltank can neutralize male Pokemon with Attract, heal itself with Milk Drink, and end lives with Rollout.
Whitney’s Gym is the third in Gold, Silver, and Crystal, and very few Pokemon that you can catch up to that point can do real damage to her team. This is another battle — like Norman’s — that forces you to attack with anything and everything. Most of the time you’ll just be hoping that, eventually, Miltank’s HP reaches zero.
2. Blue
Blue is another cheater who forgoes tradition, but are we really surprised by that? There’s no real specific type for his Gym. Instead, Blue uses a Pidgeot, Alakazam, Gyarados, Exeggutor, Arcanine, and Rhydon to take you on.
This is a challenge for several reasons — the first, and most obvious, is that a varied and balanced team is needed to beat him. All of his Pokemon are nearly level 60 and most have move sets that are a pain to deal with in Gen II.
Look at the team and you’ll see what I mean: Alakazam has Disable and Recover, Rhydon has Sandstorm and Earthquake, Gyarados has Hydro Pump and Hyper Beam, and the list goes on. This feels a lot more like a Champion battle than a Gym battle, and Blue lets you know exactly why he did become Champion at one point.
1. Sabrina
Sabrina provides the hardest fight of all Gym leaders because of how broken Psychic-type Pokemon were in Gen I. Their only weakness was Bug-type since Dark didn’t exist yet and Ghost wasn’t super effective. Her team consisted of Kadabra, Alakazam, Mr. Mime, and a Venomoth just for some toxic fun.
To make matters worse, the only damage-dealing Bug-type moves in Gen I were Pin Missile, Leech Life, and Twineedle — all of which dealt subpar damage. Those were your super-effective options against a Kadabra and an Alakazam that can use Recover, a Mr. Mime with Barrier and Light Screen, and a Venomoth that can use Poison Powder and Stun Spore for fun.
This fight is difficult for all of those reasons listed above, plus Sabrina has a Hyper Potion that she may or may not use to make the battle even harder.
There are so many Gym Leaders in the Pokemon franchise, so we may have missed a few other rough battles. Let us know which ones gave you the most trouble in the comment section below.
Featured Image Source: OLM (Pokemon Generations)
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