15 Pokémon Gym Leaders Who Are WAY Too Hard

If there’s one criticism that’s leveled at the Pokémon games, it’s that they’re too easy. Too cutesy. Too sun-shines-out-of-everyone’s-butts-y, as is often the case with Nintendo games. Sure, that’s three criticisms, and Nintendo aren’t the developers of Pokémon, but this is no time to be pernickety.

If you’ve ever seen a nuzlocke or other kind of self-imposed challenge playthrough, you’ll see what a false impression this is. With permadeath for fainted Pokémon and other such factors added, Pokémon can be as harrowing and gut-wrenching an experience as any Dark Souls. Competitive play, too, can be as hardcore as juggling lions, angry wolverines and flaming chainsaws with your feet. As any victim of flinches, critical hits, untimely freezes or any number of other BS will tell you, Pokémon is not a friendly game in any sense of the word.

Pokémon is not friendly. It is not cute. It hates you. It wants to crush your hopes and dreams into spam before your eyes and sacrifice your first born child to Beelzebub. The worst thing is, the games are sneaky about their intentions. They appear all warm and cosy, like a Chihuahua in a bathrobe, but that’s just to sucker you in.

The gym leaders are central to any Pokémon game (other than the recent Sun and Moon, which overhauled the whole system with its island challenges). They’re the bosses, I guess you could say. Unsurprisingly, a fair few of them are raging assholes. Let’s strap ourselves in and meet 15 Pokémon Gym Leaders Who Are Way Too Hard.

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15 Brock


I know, I hear you. Brock? The very first gym leader? I should burn my ancient housebrick of a Game Boy, retire from video games forever and take up a hobby I can handle, like sitting at the back of the class with the safety scissors and glitter. It’s not as clearcut as all that, though.

Sure, if you picked Bulbasaur or Squirtle, you’ll hand Brock his man-plums on a platter in about a nanosecond. A little grass or water STAB and he’s crying for his mama. If your starter was Charmander, on the other hand, you’ve got an uphill battle to the summit of Mount Screwed on your hands. At this point in the game, your choices are either to use a Double Kick Nidoran or a Psychic Butterfree against him.

Have you ever tried beating a Rock type to death with a non-STAB Scratch? It’s a bad time.

14 Norman

Via: cloud.attackofthefanboy.com

Norman ‘I’ve Got Two Slakings And I’m Not Afraid To Use Them’ Norman, from Ruby and Sapphire, isn’t a nice guy. He’s the sort of dude who you’ll find yourself standing in line behind at the store. He’ll take affront at some perfectly reasonable store policy and scream at the entirely innocent cashier who’s just trying to do their job. Because Norman, my friends, is a douchebag.

When he’s not giving people who work in retail nervous breakdowns, Norman is defending his Normal-type gym with a pair of Slaking. Dumb and Dumber, I call them, or Whup Your Ass and Whup Your Ass Harder. I spent far too long in this battle sacrificing Pokémon to the Slak-gods and trying to abuse the Truant turns, only for him to just potion them up and continue to bring the pain. Nobody likes you, Norman.

13 Sabrina

Via: 1.bp.blogspot.com

Another throwback to the good old days of Pokémon Red and Blue, it’s Sabrina. In this generation, you’ll remember, the Psychic type was utterly dominant. It was pretty well unresisted (other than by other Psychics) and its weakness was a complete nonentity. Which Bug move were you supposed to be afraid of, exactly? Beedrill getting its Twineedle on? Before the entire type chart shifted to address this, with the introduction of Dark and the Ghost weakness, Psychic was an unstoppable Arnold-Schwarzenegger-back-in-the-day of a type.

Sabrina, then, could be a real pain to beat. That Alakazam of hers was a monster, with enough speed and special (before the physical/special split, it could take also take hits from that side way too well) to sweep through you easily if you weren’t on your A game.

12 Drayden

Via: imgur.com

Opelucid City was an interesting one. In Pokémon Black, it had a fancy technological design, while Pokémon White’s Opelucid had a simpler, natural look. Depending on the version you were playing, you’d be up against a different gym leader as well. You’d better hope you were playing White, because Drayden was waiting for you in Black and he wasn’t afraid to trample all over you and mail you back to your mom in a matchbox.

The region’s final gym challenge was all about dragons (as opposed to dat base). Much like Psychic was, this was generally considered to be one of the best typings in the game, also needing a little balancing in the shape of gen 6’s Fairies. Drayden’s dragons could be a real challenge, what with that and their beefed-up levels.

11 Clair

Via: pm1.narvii.com

Sticking with the whole ‘Dragon types making you cry, rage, despair and question all of your life choices’ theme, here’s Clair. She’s the cousin of the infamous Lance, which probably tells you all you need to know about this one.

Clair’s gym is situated in Blackthorn City, back in Gen II, a region known for having Dragon specialists out the wazzoo. There’s a Dragon’s Den nearby, too; the whole place seems to be drowning in dragon. I don’t know how much dragon is too much, but we must be getting perilously close here.

Anyway, once battle is joined, Clair drops absolutely infuriating Thunder Wave-spamming Dragonairs on us. It’s an example of the series’ ‘false difficulty;’ when a battle that isn’t all that hard in and of itself becomes so when a heaping helping of BS luck is involved.

On top of that, when you actually do win, Clair won’t deign to give you the badge you’ve earned until you head into Dragon’s Den. Take a good look at yourself in the mirror, Clair, and think about what you’ve done.

10 Whitney

Via: vignette1.wikia.nocookie.net

The noble code of the Normal type gym leader goes way back in Pokémon history. The founders of the first Normal gym carved these immortal words into rock, so that fellow Normal specialists would read them and be inspired. The first rule of Fight Club is that you don’t talk about Fight Club. The first rule of Normal gym leading is be an asshole.

Now, Norman and his damn Slakings already take the cake here, but Whitney sure as hell deserves a croissant or some other kind of baked good for herself. The mistress of Goldenrod Gym back in Pokemon Gold and Silver and her infamous Miltank need no introduction. That recurring nightmare you have, where you wake up screaming ‘Don’t Attract! Please don’t! Gah, Rollout!’? It’s all her fault. She did this.

9 Wattson

Via: cloud.attackofthefanboy.com

Ruby and Sapphire’s Wattson is another example of what I call Brock Syndrome. Nothing to do with his weird beady eyes which never open, this phenomenon directly correlates which starter you chose with how screwed you are.

If you’ve got Marshtomp or Combusken in your party, you should be able to blow through this Electric type gym. Meanwhile Grovyle, while resisting Electric, can do little against Wattson’s ace: Magneton. You’re left with Makihita, maybe, or Geodude with a ground move. Kind of clutching at straws, there, especially if that dastardly and bastardly Voltorb decides to Selfdestruct on you at the worst moment. Which it loves to do. It is Voltorb’s only goal in life, giving him a sense of purpose and belonging that a string of failed relationships has never been able to fulfil.

For all of these reasons, I’ve always filed Wattson in the drawer marked Much More Trouble Than I Was Expecting.

8 Crasher Wake

Via: otakukart.com

Now, if you must build a mono-type Pokémon team (which is about as smart as mocking Mike Tyson’s lisp and reminding him of that ear incident), Water is one of the better typings to go for. It has only two weaknesses and access to Ice moves out the wazzoo means it can cover one of them, Grass, relatively well. As such, it’s no surprise to find a Water specialist showing up on this list. Make way for Crasher Wake.

This charismatic old topless guy benefitted greatly from Pokémon Diamond, Pearl and Platinum’s new mechanics. He’s got a Floatzel with one of those fancy-ass new priority moves, way to go for that one Crasher. Most importantly, he’s got a Gyarados which doesn’t bite the big one, now that it’s actually got physical Water moves on deck at freaking last. Read that Waterfall to the face and weep, challengers.

7 Winona

Via: i.ytimg.com

As with Water, Flying can be a relatively effective type for a mono team. It’s surprisingly diverse in terms of primary typings, which allows you to switch around and cover certain threats that could otherwise just OHKO everything you have one by one. As Pokémon Emerald players will know, Winona has this down pat. The whole battle was one big feathery middle finger.

Her party of five flyers pulled an amazing array of tricks out of their asses. Sunny Day Tropius, Altaria busting out that Earthquake (and using Dragon Dance, which it had no freaking business learning)… I was caught off guard so many times during this match. Not to mention the fact that, by this point, those damn rotating gates had made me angry enough to kick a kitten into a ceiling fan.

6 Koga

via pokemon.wikia.com

Ah, Koga. While he wasn’t all that much of an issue in Red and Blue, he seemed to become pretty damn embittered by that defeat. He sat at home for a couple of generations, bitching under his breath, scrawling in notebooks. Like a mad scientist trying to build a death ray in his basement. Which would’ve been preferable really. When Koga made his return, he was back with a troll-arama vengeance.

The battle was a blur of Minimize, Toxic (so that your HP slowly ticks down while you CAN’T HIT THAT FREAKING MUK) and Smokescreen for extra evasion-based goodtimes. Then there’s that Selfdestruct on Koffing, just because. Oh, and did you want to get this torture over with quickly by hitting them all with super effective Ground moves? I bet you did. Wouldn’t that have been peachy? Not today, buddy boy, Koffing and Weezing are both immune via Levitate now.

5 Juan

Via: moe.animecharactersdatabase.com

Goddamn it, Juan. What was I just saying about false difficulty? You were juan hell of a pain in my butt back in the day, for one sole reason: Kingdra. As much as I love that Pokémon, yours seemed to have come straight from Satan’s underworld u-bend to cause pain and suffering for all humanity.

Granted, Juan’s other Pokémon weren’t really up to much, but THAT FREAKING KINGDRA. More than anything else, this battle is a test of the player’s luck. If all goes well, it’ll just use Dragon Dance a few times (with no physical moves to speak of) and so be completely harmless. If not, it’ll be a festival of Double Team spam, leaving you crying in the foetal position on the kitchen linoleum at the injustice of it all.

4 Elesa

Via: cdn.bulbagarden.net

When it comes to competitive Pokémon, I’ve always been a hyper offense sort of guy. I favour tactics like rain rushdown, which can curl up and die pitifully like a dehydrated houseplant when it loses momentum, but is horribly devastating if you can keep it up. Hitting hard and fast is the name of the game, and Elesa sure as hell got that memo.

She stuck the damn memo on her forehead so she’d remember it at all times, is more like it (the memo’s on a post-it, apparently). All you need to know about this Electric type leader is that her super-fast Volt Switching Emolga is surprisingly deadly and the rest of her team follows suit. Don’t even go near Nimbasa City without a Ground type.

3 Fantina

Via: media.pocketmonsters.net

Man, had Ghost Pokémon come a long way by Diamond and Pearl. Back in the dark days of generation one, there was a grand total of one ghost (family) and slim to bupkus STAB moves for it to utilise. Thanks to weird glitchiness, Psychics were immune to Ghost and that’s all kinds of freaking wrong right there. Can you imagine if Ice was immune to Fire? That’s no freaking world I want to live in, I can tell you that.

By Fantina’s day, ghosts were a force to be reckoned with. To get your hands on her Relic Badge, you’ll have to withstand a metric crapton of status moves, as well as the power of meta mainstay Gengar. For Platinum, said ghost was actually cut from the team, which says it all really.

2 Lt. Surge

Via: theinsightfulpanda.com

Impatient little bugger that I was back in the day, Lt Surge’s infamous dustbin puzzle was the bane of my existence. Luck-based messing around is rarely fun. I didn’t have too much of a grasp on either the intricacies of the type chart or the fact that patience is a virtue (as grandma used to say), both of which were essential factors in giving the OG Electric leader the whupping he deserved.

So yep, this battle went south on me many times. Maybe all that ‘aim for the horn’ crazy talk from the anime made me distrustful of the virtues of Ground types here. Let’s not forget, also, that Surge’s Pikachu and Raichu had Double Team and priority in Fire Red and Leaf Green. Craptacular priority in Quick Attack, true enough, but I’m still pissed about it.

1 Blue

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After the original games, Giovanni couldn’t quite keep his legitimate gym leader job going any more. You can see how going into hiding after the destruction of your ruthless criminal syndicate can leave little time for whupping uppity kids with Fissure hax. For Gold and Silver and their remakes, then, his place in Viridian’s gym was taken by Blue.

This guy broke the cardinal rule of gym leaders by having a fully-balanced, nuts-to-mono-type team. We don’t tolerate that sort of outrageous behaviour around here, Blue, so that’s strike one already. My other issue with this battle was the levels of his ‘mon, which made some of them a nightmare to deal with. Still, it was an unusually strategic fight and nothing less than you’d expect from the former Pokémon champion.

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