The real place you’ll prove your mettle is in the Gyms of each game, where you’ll battle the 8 Gym Leaders of the region for an opportunity to battle the Elite 4. Theoretically, each Gym Leader should be more difficult than the last. But this is not always the case. For example, Blaine is the second-to-last Gym Leader in gen 1, but is one of the easiest fights of all time. Well the Gym Leaders in this list are tough because they either have a massive type advantage, a singularly strong Pokémon, or are able to cover a good amount of their weaknesses. But which leader is going to give you the hardest time? Let’s find out.
20. Brock (Yellow)
Let’s start at the very beginning (a very good place to start). The Rock-type gym leader Brock was the start of many players’ Pokémon gym experience, and he was always pretty simple. Well, if you chose Squirtle or Bulbasaur, you’d have no problem. Heck, even Charmander could make quick work of Brock’s Pokémon because of their low Special Defense! But the difficulty got amped up in Pokémon Yellow. You have to start with a Pikachu who only learns Electric and Normal-type attacks by level up. That means his Geodude and Onix will either be taking half damage, or no damage. But Brock takes this end spot in our ranking because there are a lot of Pokémon on your way over that can help you out: Mankey, the Nidorans, or Butterfree. But if you’re a kid who’s not leveling up any of their Pokémon who isn’t Pikachu (like I was), then you’re about to get rocked.
19. Bugsy (HG/SS)
I’ve always loved Bugsy. His hair and outfit remind me of the “Berries and cream” guy from the Starburst commercials. But even though he may look like a wussy British schoolboy, his team is no joke. Bugsy starts off with Scyther, one of the coolest looking Pokémon of all time. The Mantis Pokémon will then quickly U-turn out to either Metapod or Kakuna, who are much less scary. But this serves as an excellent way to chip away at the Pokémon you start with, which will have the biggest advantage against Scyther. So what’s the best way to handle Bugsy? Well, Cyndaquil is a great choice. But in case you chose a different starter there are also a ton of Geodudes nearby, as well as an Onix you can trade for. Bugsy isn’t impossible. But it can be terrifying if you’re unprepared.
18. Grant (XY)
Grant is the cool rock climber from Kalos with hair that looks like the Aggro Crag. And at first, the battle seems easy: another Rock-type gym leader. However, his Pokémon are much harder to deal with than you’d think. Grant focuses on Fossil Pokémon, and his first one is a doozy. Amaura is a Rock/Ice-type with pretty balanced attack stats. It can easily hurt you with STAB Aurora Beam, Rock Tomb, and Take Down (because of Refrigerate). Plus, this thing carries Thunder Wave so it can slow you down. Next is Tyrunt, a Rock/Dragon-type with a massive 89 base Attack stat. Especially this early on in the game, that’s no joke. Combine this with Bite and Tyrunt’s ability Strong Jaw and your Pokémon will be hurting. Fortunately, Grant’s Pokémon are slow. All you really need is a decently speedy Fighting-type – and there are a couple in the neighboring areas.
17. Lenora (BW)
While there are a lot of Gym Leaders on here because of a single strong Pokémon, there’s only one who has a single strong move. And that’s Lenora. Lenora is the second Gym leader in Black and White, and she uses Normal-type Pokémon. While this may seem simple, Retaliate makes it anything but. Retaliate is a move that normally has a 70 base power, but it doubles if a party member fainted in the previous turn. That means that her fully evolved Watchog suddenly has a 140 base power move to absolutely destroy whoever’s in front of her. Other than that, Watchog isn’t that good. But if she takes out your best Pokémon in one single hit, chances are you aren’t going to win.
16. Valerie (XY)
One of the best additions in X and Y was the brand new Fairy-type. Finally there was something that could hard check Dragons and give a reason for Poison-types to exist! Unfortunately, Valerie doesn’t really care if you have Poison-types. Her first Pokémon, Mawile, is part Steel-type so she’s completely immune to Poison attacks. And her Pokémon right after that is the Psychic-type Mr. Mime. So if you do bring a Poison-type Pokémon to this battle, you’re screwed. Not to mention that her best Pokémon, Sylveon, hits like a truck! But if you can’t bring a Poison-type, what can you do? A Steel-type. Bring a Steel-type. Preferably one with a Ground-type move. Next!
15. Whitney (GSC)
Everyone reading this knew Whitney was going to be here. Everyone who grew up playing Gold, Silver, or Crystal knew the true terror that was her Miltank. It could immobilize you with Attract, regain health with Milk Drink, and deal out tons of damage with Then why isn’t Whitney higher on this list? Well, kids are stupid. And there are a few great options in handling Whitney, like the Machop that you can literally get a few buildings away, or just try putting Miltank to sleep before it can hit you. As a kid, Whitney was terrifying. And while I’m not as scared of her now, she easily makes it on for nostalgia’s sake.
14. Elesa (BW)
Every Electric-type Gym has to deal with Ground-types. Just look at poor Wattson in Ruby and Sapphire. However, Elesa figured out a great way to avoid that strategy by using Emolga. Emolga is an Electric/Flying-type Pokémon, making it immune to all of those pesky Ground-type attacks. Suddenly you can’t just Bulldoze your way through all of her Pokémon. On top of this, her whole team utilizes the same switching strategy as Bugsy, but with Volt Switch. There’s just one issue: having a Ground-type kind of ruins her strategy of switching in and out since they’re immune to Volt Switch. And while you can’t hit her Emolgas with a Ground-type move, most Ground Pokémon learn Rock-type moves which will be Super Effective. If you don’t have a Ground-type, this’ll be rough. But if you stop by the Desert Resort, you should be ok.
13. Piers (Sword/Shield)
Piers is easily one of the coolest Gym Leaders in all of Galar. The fact that he refuses to use Dynamaxing is awesome, and really shows how much of a rebel he is! This is perfect for his fantastic Dark-type team. What makes Piers’ team so effective is how it addresses most of the Dark-type weaknesses. Malamar can make quick work of Fighting-types with Psycho Cut and Skuntank can resist Fairies and poison them with Toxic. Not to mention that Obstagoon is just a beast and can shrug off most hits that come its way! The best answer for Piers is to get your hands on a good Bug-type Pokémon and teach it the new and improved Leech Life. Even getting neutral damage on Skuntank, you should have no problem.
12. Koga (FR/LG)
Koga may not be the hardest leader, but I think he officially wins the award for most annoying Gym in all of Pokémon. First of all, you have to navigate invisible walls in order to get to the ninja master. While this may seem easy now, I remember as a kid hanging out with a bunch of friends with graph paper drawing out the layout of all the walls. And then there’s his team. Each Pokémon is completely built around the move Toxic. That means they need to poison you and survive until you die. They do this by lowering your accuracy or raising their evasion. Well, Earthquake is accurate and hits for Super Effective damage! Why not just use that? Well, 3 of his 4 Pokémon have Levitate, so you’re out of luck. Not to mention that his Weezing has Self Destruct. And if it kills your last Pokémon with it, you lose. Yes, you can bring in a Psychic-type to make quick work of Koga’s entire team, but you’ll have to hit them first.
11. Flannery (Emerald)
I remember back when I first played Pokémon Ruby, Flannery was the first brick wall I came up against. I thought her team was really rough with that Torkoal! Then I played Pokémon Emerald. Holy Crap. Flannery’s team is full of strong Special Attackers who are all sporting Overheat, a powerful Fire-type attack. This is increased even more by each member of her team having Sunny Day. Not only does this boost up all of her Fire-type moves, but it also weakens Water, which is her main weakness. This makes all of her Pokémon dangerous, especially Camerupt and Torkoal. The best option against her is honestly Marshtomp. If you didn’t start with Mudkip, then I feel sorry for you right here. Thank goodness none of her Pokémon have Solar Beam, or she’d be in the top 5 no question.
10. Volkner (DP)
Volkner is probably the best Electric-type Gym Leader in all of Pokémon, and that’s because he doesn’t only use Electric-type Pokémon. His first weird choice is Octillery. While not the strongest of Pokémon, Octillery has insane coverage and can wreck most Pokémon with its combination of Charge Beam, Octazooka, Aurora Beam, and Bullet Seed. Ground-types don’t stand a chance! The second is his Ambipom. It’s only attacking move is Shock Wave, but it can also boost its Special Attack and Speed with Nasty Plot and Agility. But things get really scary with Baton Pass. Now Ambipom can pass these boosts to any Pokémon on the team it wants. And if either Luxray or Octillery get this, it will not be fun. I love that Diamond and Pearl took a risk by giving Gym Leaders Pokémon you wouldn’t think they had. This makes for easily the most competitive gyms in the series.
9. Misty (FR/LG)
It’s nice to see that every character from the Anime isn’t a joke in-game. Even though Misty is only the second Gym Leader in Kanto, she’s easily one of the toughest in the game because of her Starmie. Since Starmie evolves by a Water Stone, you’re now battling a fully-evolved Pokémon early on in the game with insane stats. That 115 Speed and 100 Special Attack can destroy just about every monster you can get at this point in the game. Combine this with Water Pulse, a move that deals decent damage and can confuse you, and Recover… and this battle can go on forever. There aren’t a lot of answers for Misty’s team. Your best bet is to get a Grass-type with Razor Leaf and pray that it crits. Other than that, it’s just luck or grinding levels.
8. Maylene (Platinum)
While some teams may have good coverage or an incredibly strong Pokémon, Maylene’s team seems to have both. She starts off with a Meditite and Machoke. Machoke is strong because of its awesome Attack stat, while Meditite takes advantage of its Psychic-typing and ability Pure Power, which doubles its Attack stat. They both can also take on Flying-types with Rock Tomb. But the real star of the show is Lucario. With its Steel/Fighting-typing, Lucario only has weaknesses to Ground, Fighting, and Fire-types. Lucario can easily go head to head with most other Fighting Pokémon, and can destroy Fire-types with ground move Bone Rush. Really, Lucario is just way too good at this early stage in the game. Your best bet is to get a good Ground-type and hope for the best.
7. Norman (Emerald)
Norman: the only father a main character in Pokémon has ever known (seriously, look it up!) In order to continue to the other side of Hoenn, you have to prove to him (and yourself) that you’ve become strong enough. And it only makes sense that this battle is incredibly hard. If you think you can just get a good Fighting-type and tear through Norman’s team, you’ve got another thing coming. He starts off with a Spinda that knows Psybeam, and since most Fighting Pokémon have such bad Special Defense, it won’t go over well. What about Ghosts? Most of his team runs Faint Attack. Then how about statuses like Poison? The gym’s signature move is Façade, whose power doubles when status’d. Plus, all of his Pokémon are just unbelievably strong. Vigoroth is fast and Linoone utilizes Belly Drum. But the biggest threat is Slaking. Even though it has the worst ability in the game with Truant, its stats are incredible, with most of them at 100 or higher. It’s fitting that Norman gives out the Balance Badge. Because in order to defeat him, you’re going to have to make a team that really works well together. Good luck.
6. Marlon (B2W2 Challenge Mode)
Black 2 and White 2 had Challenge Mode, an additional playthrough where all of your opponents are stronger than in the regular game. And the final Gym Leader, Marlon, takes total advantage of this. Marlon is a Water Gym Leader that starts out with Wailord, a Pokémon with a ton of HP. This means it’ll have a great chance to use either Earthquake to take out an opposing Electric Pokémon, or Rain Dance to support Mantine, who has the ability Swift Swim. This means Mantine can take out Grass-types no problem. And while Marlon’s favorite Pokémon is Jellicent, the scariest is easily Carracosta. Carracosta will take advantage of its ability Sturdy to set off a guaranteed Shell Smash, boosting both attacking stats and Speed. Suddenly, Carracosta is an opponent who can destroy your entire team. All of this with the extra layer of difficulty with Scald, a Water-type attack with a chance to burn. Seriously, Marlon is no joke.
5. Clair (GSC)
It’s funny to me that Clair is considered the weaker Dragon Trainer to Lance, because I had a much harder time with her than the Pokémon Champion. Clair starts off with 3 Dragonair. However, each one has a different elemental attack to take advantage of. And you won’t know which one it is until it attacks. Combine this with each of them having Thunder Wave, and you can get flustered quickly. But the scariest part of her team has to be Kingdra. You see, your best answer against Clair would be an Ice-type. And you just got a hold of some good ones right before this gym! But Kingdra is a Dragon-type which isn’t weak to Ice, specifically because of its Water dual-typing. Plus, Kingdra can wreck any of the Ice-types coming for her with a combination of Surf, DragonBreath, and Hyper Beam. Clair’s team is awesome and can easily defeat a team that isn’t completely prepared.
4. Raihan (Sword/Shield)
Raihan is just further proof that Sword and Shield have the best gym challenges in all of the Pokémon games. While Raihan claims to be a Dragon-type trainer, his team is actually quite varied, with only two dragons. Raihan’s main goal is to set up Sandstorm with Gigalith or Sandaconda. After this, he can take advantage of it with Flygon or Duraladon. They can also use Breaking Swipe to lower your attack so that your Pokémon will stick around longer to get hurt by the Sandstorm. Plus, Duraladon’s Steel-typing eliminates all 3 of the Dragon-typing’s weaknesses. This team is stacked! Raihan is tough. And there isn’t one easy strategy that can defeat his team. It’s just pretty well-balanced and a fun challenge in battle!
3. Winona (RS)
In a series with a history of weak Flying-type Gym Leaders, Winona stands out as probably the toughest battle in all of Hoenn. Swellow is unbelievably fast with a great attack stat, so you’d think the answer would be to come in with Rock-type Pokémon. Well, they now have to contest with Pelipper and Skarmory. Pelipper has Water Gun and Supersonic, so it can be tough to actually hit this thing. Meanwhile, Skarmory is one of the best defensive Pokémon of all time, and can make quick work of Rock-types with Steel Wing. No worries, I’ll just bring an Electric-type! Well, then here comes the coup de grace: Altaria. Altaria is Dragon/Flying, so electric attacks will be neutral. This gives it an opportunity to use Dragon Dance, boosting its Attack and Speed. Now all Altaria has to do is Earthquake and Aerial Ace its way through the rest of your team. Game over. People complain all the time about Whitney’s Miltank or Cynthia’s Garchomp. But if you ask me, there’s no more terrifying Pokémon than Winona’s Altaria.
2. Sabrina (Red/Blue)
Sabrina’s Psychic team in Red and Blue is easily one of the most frustrating teams in all of Pokémon. This isn’t because of how great her strategy is, or how strong her Pokémon are, but because of how broken the original games were. The Psychic-type in Gen 1 is unfairly powerful. Since Special Attack and Special Defense were combined into a single stat, these Pokémon were bulky and sweepers at the same time. Not to mention that nothing resisted Psychic attacks. All of her Pokémon could just sweep through you. Especially Alakazam. And since Critical hits were determined by speed, Alakazam’s insane Speed stat made it a critting machine! Combine this with a high Special stat and there was no way you could win easily. And what’s worse is that none of the checks for Psychic-types actually work. The only Ghosts are part Poison-type, so they’re weak to Psychic-type attacks. Not to mention there aren’t any strong Bug-type attacks in gen 1 that can really do damage… Your best option is to just get some physical powerhouses and try to strong arm your way through Sabrina’s team. Really, there isn’t any core strategy here. Just tons of time spent grinding up levels.
1. Blue (GSC)
Blue is easily the most difficult Gym Leader of all time. The character who was your rival in Red, Blue, and Yellow went on to become the leader of the Viridian City Gym after Giovanni left. And instead of taking up the Ground-type mantle, he decided to just run the gym with a championship team. No biggie. His team consists of six of the strongest Pokémon in the game (at the time of gen 2). Each one could conquer the weaknesses of another, and they could all take you out. They also all utilized weather to set each other up for stronger hits. I remember as a kid when I finally got to this point. I was shocked and so freaking excited to take him on. Especially after all the other gyms in Kanto were so easy… In the end, it had to be Blue. His team is the most varied and the most challenging out there. You’re my boy, Blue. Smell ya later!
