Intro: These Guys Mean Business!

The Pokémon franchise has never been known for its difficulty, but there are some battles that have frustrated many trainers time and time again. I have some not-so-great memories of getting absolutely wrecked by one gym leader over and over again, but, at the very least, it was beyond satisfying when I finally beat them. The gym leaders on this list are in a whole new league (literally) than their colleagues. 

What Constitutes a Strong Gym Leader?

The strongest gym leaders stand above those who are moderately challenging or pathetically easy for the following reasons…

• A diverse array of Pokémon - while the majority of gym leaders specialize in one type of Pokémon, the strongest ones are those that take advantage of secondary-typings to provide more coverage against the player.
• High-leveled (at the point where the player faces them) - while some of these gym leaders are introduced earlier than others, we have to acknowledge their toughness in proportion to when in the story we face them. Let’s take Falkner of the Johto Region and Roark of the Sinnoh Region, for example. They are the first gym leaders of Pokémon Gold, Silver, and Crystal (and their remakes) and Pokémon Diamond, Pearl, and Platinum (and their remakes), respectively. Falkner is a complete pushover as far as first gyms go, while Roark can be challenging for a first gym leader.
• Clever movesets - many gym leaders employ tactics and movesets to add depth and strategy to their battles. You’ll need to be thoughtful with your approach when taking down the strongest of the bunch. 
• Good Pokémon - this is obvious, but it is important to mention. If we take a look at Pryce, the seventh gym leader in Johto, his Pokémon are lower-leveled than those of the previous gym leader! For a penultimate gym leader, that is just plain sad!

Anyways, let’s get on to the list. These twelve gym leaders are the strongest you will meet in your Pokémon journeys. Don’t take them lightly, or you’ll be in a world of hurt!

12. Nanu (Strong)

Ula'ula Island Kahuna Nanu - Pokémon Ultra Sun and Ultra Moon

This Dark-type trainer and part-time cop is the Kahuna of Ula’ula Island, and is battled in Pokémon Sun and Moon, as well as Pokémon Ultra Sun and Ultra Moon. These two duos of games strayed away from the traditional Pokémon League formula. In lieu of gym leaders, we had to go through the island challenge, where we ventured throughout the four islands of the Alola Region. Each island has a select number of trials hosted by Trial Captains, where the player must progress through an area, and battle a Totem Pokémon at the end to complete the challenge and receive a stamp from the Trial Captain. After all of an island’s Totem Pokémon are defeated, the Kahuna shows their face and engages in battle with the player. The four Kahunas are, more or less, the Alolan equivalent of gym leaders.

Nanu is the third Kahuna we must battle in the games, and the most difficult of the four. Unfortunately, his rank on this list is mostly affected by outside forces. Sun and Moon are widely considered the easiest games in the franchise, and while Ultra Sun and Ultra Moon are considered the most difficult, Nanu’s team hardly changed from the original, with each of his Pokémon being five levels higher with no new moves. On top of that, the two preceding Kahunas, Hala and Olivia, specialize in Fighting and Rock-types, two types that are easy to counter. The final Kahuna, Hapu, is a Ground-type trainer in a region where there’s no shortage of super-effective Water, Grass, and Ice Pokémon. 

In all of his appearances, our initial battle with Nanu pits us against three Pokémon: Sableye, Krokorok, and Alolan Persian. His Sableye is not very threatening, but being part Ghost-type meant it was only weak to the Fairy-type. We did not have many options for Fairy Pokémon in Alola, and the ones we could choose from at this point either didn’t yet have access to strong Fairy attacks or, in the case of Cutiefly and Ribombee, were part Bug-type, and thus susceptible to Sableye’s Rock-type Power Gem move. The crafty little spirit also knew Fake Out, which could only be used on the first turn that Sableye entered battle, but caused the opponent to flinch. Thanks to that, it was almost guaranteed that you wouldn’t be able to take down Sableye in a single turn.

Next up is Krokorok, the Ground/Dark type crocodile. Krokorok could use Swagger to sharply raise your Pokémon's Attack stat while also inflicting confusion. Confused Pokémon have a fifty-fifty chance of attacking themselves, so any self-inflicted damage would hurt more with the added attack boost. Krokorok makes up for his run-of-the-mill Speed with Assurance, a move that doubles in power if the user has already sustained damage in the same turn. We also have to deal with Crunch and its chance to soften our Defense stat and, of course, the almighty Earthquake. Unlike Sableye, however, Krokorok has more weaknesses to boot, with stronger options for Water, Fighting, and Grass attacks.

Nanu’s Alolan Persian is one of the strongest Pokémon in the entire game. Unlike the Normal-type Persian that hails from Kanto, this black cat has the ability Fur Coat, which doubles her Defense stat throughout the battle. Physical attackers are in for the long haul here. With the lack of strong Fairy moves at this point in the adventure, and the fact that the better Bug and Fighting attacks were mostly physical, Alolan Persian can tank a lot of hits. Oh, and watch out for the Z-Move that Nanu and Persian have up their sleeves. Sun and Moon introduced Z-Moves of each type that, when used by upgrading a regular attack of the same type, could do incredible amounts of damage. Persian’s Black Hole Eclipse is a rude awakening, if I must say so myself! Nanu is Alola’s strongest Kahuna, and it’s not even close.

The grin says it all…

11. Maylene (Strong)

Veilstone City Gym Leader Maylene - Pokémon Platinum

While Fighting-types are common to the point where there are plenty of options to handle them, Maylene begs to differ. Maylene is the third gym leader faced in Pokémon Diamond and Pearl and its remakes, and the fourth in Pokémon Platinum. Maylene’s team of three knows how to cover their weaknesses. I should also mention that the Fairy-type did not yet exist when Maylene first appeared, so our options were considerably more limited.

She leads with the Fighting/Psychic-type Meditite. The zenned-out monkey knows Maylene’s signature attack, Drain Punch, in all three renditions, to do respectable damage while also restoring Meditite’s HP. In the original DS trio, Meditite has Confusion to complement her Psychic-typing. While Confusion isn’t too strong of an attack, it has a chance to confuse your Pokémon, so watch out! Meditite’s remaining moves include Detect, to waste time and make your attacks useless, Fake Out, to force your Pokémon to flinch, and Light Screen to bolster the whole team’s Special Defense. Oh yeah, Meditite’s ability is Pure Power. This doubles the user’s Attack stat… ouch. This monkey ain’t messing!

Maylene’s Machoke also packs a real punch. Machoke knows Rock Tomb in all three games to clip the wings of any Flying-types you may have brought in. In Brilliant Diamond and Shining Pearl, he also knows Knock Off to handle any Psychics. This bodybuilding brute has a different Fighting-type attack dependent on which version you are playing. Regardless, Machoke is a threat with his raw Fighting power. Other tactics include using Foresight to render Ghosts vulnerable and Focus Energy to increase the likelihood of landing a critical hit. Oh and don’t try using status conditions either. Maylene’s Machoke has the Guts ability, where his Attack skyrockets when dealing with an ailment. You’re in for a beating here!

If you managed to take out her first two battlers, don’t assume you can cruise the rest of the way. Maylene’s Lucario is the strongest Pokémon you will face in the first half of your Sinnoh journey. Lucario has the Steel-typing as a secondary type, eliminating all of the Fighting-type’s regular weaknesses. Like Meditite, Lucario can use Drain Punch to whittle away your health in seconds flat, while recovering his own. Not to mention that any Fairies you battle with in the remakes will fall victim to Metal Claw. Maylene’s Lucario on his own makes this gym battle challenging, but with two other reliable Pokémon centered around her ace, Maylene is one of the toughest early-game gym leaders in the entire franchise.

Maylene, tell me something I don’t know!

10. Volkner (Very Strong)

Sunyshore City Gym Leader Volkner - Pokémon Brilliant Diamond and Shining Pearl

If you thought Maylene was tough, just wait until you only need one more badge. Battling Sinnoh’s final gym leader, Volkner, will leave you in shock, literally, as his electric Pokémon can easily zap challengers into submission.

Pokémon Diamond and Pearl and their remakes had some questionable choices of available Pokémon, and this affected some of the bosses too. Volkner is perhaps the most notorious example of this. Only half of Volkner’s team is Electric-type. Along with his Raichu and Luxray, he also has the Normal-type Ambipom and the Water-type Octillery. This can definitely throw unsuspecting players off guard. Platinum fixes this by replacing the two with Jolteon and Electivire, but this guy is just as prepared here. Volkner’s signature move is Charge Beam, which, while not the strongest Electric move out there, has a very high chance to up the user’s Special Attack. If he gets off enough Charge Beams, Volkner’s Pokémon can cook your goose in the blink of an eye!

Volkner’s Raichu is one fast Pokémon. This is made even worse if Static activates upon contact with the Electric Mouse, paralyzing anyone who touches him. Raichu can also lay down Light Screen in Diamond and Pearl and has solid coverage including Brick Break, Focus Blast, and Signal Beam. In Platinum, you’ll be faced with even more speed in Jolteon who can also cripple your Speed with Thunder Wave and work around the Ground-type immunity to Electricity with Iron Tail. Volkner’s speed tactics early on are sure to wear down your team once his hard-hitters enter the fray. 

While Ambipom and Octillery aren’t too special as Volkner’s wild cards, you should still be wary. Ambipom can increase his Special Attack with Nasty Plot or Speed with Agility. The handsy primate can follow up with Baton Pass to swap in another teammate and pass on the boosts to said teammate. Octillery, on the other hand, can get lucky with boosted critical hits from his Sniper ability, and responds to Grass Pokémon with a super-effective Aurora Beam.

Luxray and Electivire are Volkner’s powerhouses, and a true test of your readiness for the final stretch of your adventure. Luxray can handle Ground-types with Ice Fang, while also boasting coverage options such as Crunch, Iron Tail, and Fire Fang. These moves’ added effects can come into play here to inflict a status or soften Defense. While the Platinum-exclusive Electivire doesn’t excel with coverage, it makes up with strong physical moves designed to knock out the opposition with ease. Also, if you’re stupid enough to bring in your own Electric-type, you might activate Electivire’s Motor Drive, which absorbs Electric-type attacks to increase his Speed. No matter which version of Sinnoh you’re playing through, Volkner is a formidable final gym leader, and worthy of being one of the toughest gym leaders in the franchise.

All amped up!

9. Tate and Liza (Very Strong)

Mossdeep City Gym Leaders Tate and Liza - Pokémon Emerald

The third generation introduced Double Battles into the core gameplay mix. Pokémon Ruby and Sapphire, the new games of the generation, were sure to bring this new mechanic into play, and our penultimate gym challenge showed us why Double Battles are tougher and require much more thought.

The psychic twins, Tate and Liza, only use one Pokémon each (two each in Emerald), but their battling tactics make this gym battle shine in quality rather than quantity. Their aces are Lunatone and Solrock, the Rock/Psychic sun and moon duo. Both Lunatone and Solrock have the Levitate ability, thus being immune to Ground-type attacks. Solrock’s movepool included Sunny Day, SolarBeam, and Flamethrower. Water Pokémon found their moves weakened by the sun, and would be easily blasted by SolarBeam which, thanks to the weather, would not require a turn to build power. Meanwhile, Grass-types, Steel-types, and Bugs will be burnt to a crisp with Flamethrower, made even more powerful by the bright sunlight. Even with Solrock’s mediocre Special Attack, the sun made up for this by allowing it to attack more swiftly. In the remakes, Omega Ruby and Alpha Sapphire, Solrock also has Rock Slide to take advantage of its other type and solid physical Attack. Lunatone doesn’t boast the same type coverage, but could aid itself and Solrock with Light Screen and put opponents to sleep with Hypnosis. While neither one had an answer for Ghost-types or Dark-types, there were limited options for those kinds of Pokémon, and neither type had a move with more than eighty base power. Tate and Liza’s intergalactic rocks are a destructive, dynamic duo. 

In Pokémon Emerald, the twins lead with a Claydol and a Xatu, with Lunatone and Solrock waiting in the wings. Claydol can decimate your Pokémon with Earthquake, and its flying-type partner wouldn’t feel a thing, while the Psychic/Flying Xatu could sew mayhem with Confuse Ray and set up Sunny Day, allowing Solrock to jump right in to battle without needing to set up the sun itself.

For those of us who think we can get away with the all-out offense tactic in Double Battles, Tate and Liza taught those fools a lesson. As the old saying goes, “two heads are better than one!”

Double Trouble!
 

8. Larry (Very Strong)

Medali Gym Leader Larry - Pokémon Scarlet and Violet

Our most recent set of games, Pokémon Scarlet and Violet, introduced an open-world format, where we could explore the Paldea Region freely and conquer the game’s challenges in any order we desired. While you could make things difficult for yourself and go right into battling Pokémon ten times your level, let’s assume you’re a sane person and did things in a logical sequence. One battle stands out, and that would be the fifth gym battle against the Normal-type leader, Larry. 

Pokémon Scarlet and Violet introduced the Terastral phenomenon to the series. Basically, a Pokémon has a “Tera Type” that can differ from its regular type(s) to drastically mix things up in combat. Each Gym Leader’s ace could take advantage of this mechanic. To begin this battle, Larry sends out a Komala, who is pretty much a pushover. The only real problem this drowsy bear poses is if she uses Yawn to put your Pokémon to sleep. Since the status activates on the following turn, you can simply switch your Pokémon to prevent it from dozing off, but you can inevitably waste turns by switching on and off to avoid falling asleep. His Dudunsparce is a bit more threatening, as she has the Serene Grace ability to increase the likelihood of an attack’s secondary effect(s) kicking in. With her two attacks being Drill Run and Hyper Drill having high critical hit ratios, Dudunsparce will be landing critical hits more often than not. 

Once he’s on the ropes, Larry will send out the Normal/Flying Staraptor and Terastralize him into a pure Normal-type (Larry is the only gym leader in Paldea whose ace is of his type specialty before Terastralizing; all the others Terastralize a Pokémon of a completely different type). Although Staraptor is now more susceptible to Fighting-types upon Terastralization, he can still leave a bruise on Fighting Pokémon with Aerial Ace. Even with the strong Fighting-types we can catch in Paldea, Staraptor’s Intimidate ability will lower your Pokémon’s Attack upon entering battle, which makes this scrap only more difficult. 

Even if you are using your best discretion and are playing through Pokémon Scarlet and Violet in a logical sequence, Larry is still a tough Gym Leader to face, and, in proportion to the difficulty scale, is the most difficult Gym Leader in Paldea.

Tera Power, Activate!
 

7. Valerie (Very Strong)

Laverre City Gym Leader Valerie - Pokémon X and Y

For the first time in fifteen years, we were introduced to a new Pokémon type upon the release of Pokémon X and Y. With the Fairy-type now in the mix, it was almost guaranteed that one of the Gym Leaders or Elite Four members in Kalos would specialize in Fairy-type Pokémon. Sure enough, upon reaching the sixth gym, we met Valerie, and her trio of pixies, who showed us why we shouldn’t underestimate the new type. Fairy-types were only weak to Poison and Steel-types, and were strong against Dragons, Fighters, and Dark-types, all of which only had a couple of weaknesses prior to X and Y (in fact, the Ghost/Dark-types, Sableye and Spiritomb, had no weaknesses at all before the introduction of Fairy-type Pokémon).

Valerie leads with a Mawile, which was given Fairy as a secondary type on top of Steel. Mawile’s typing made her immune to Poison, and neutralized Fairy’s weakness to Steel, while the new Fairy-type eliminated Steel’s weakness to Fighting. Although Mawile’s stats are laughable and Valerie’s had a terrible moveset (no Steel or Fairy moves), it can be a rude awakening to see this thing if you didn’t do your research. 

Similarly to Mawile, Mr. Mime gained the Fairy-type to complement the Psychic-type. She (yes, we have a female Mr. Mime here) takes advantage of her Special Attack with Psychic and the new Dazzling Gleam. Mr. Mime’s weaknesses to Dark and Bug were zeroed out, and, although now weak to Poison, she could still obliterate any Poison-types with Psychic power. Our options for Steel and Ghost-types were also limited, and many of them were hindered by a lack of offense, speed, or secondary-typings. Mr. Mime also has Light Screen and Reflect up her sleeve to weather attacks more easily, possibly giving Valerie’s ace some good support.

Valerie’s Sylveon brought us our eighth unique Eevee evolution, and, my goodness, this is a good one. Sylveon is a beast with his Special stats, and can cover up his lackluster physical Defense by lowering the opponent's Attack with Charm. You’ve got your work cut out for you if you don’t want to find yourself tied in Sylveon’s ribbons. Valerie gave players a good first impression on Fairy-types, and they have been a staple in the series ever since.    

All’s Fair(y) in a Pokémon battle!
 

6. Elesa (Extremely Strong)

Nimbasa City Gym Leader Elesa - Pokémon Black 2 and White 2

Despite only being Unova’s fourth Gym Leader, Elesa is the toughest Gym Leader in both Pokémon Black and White and their sequels Pokémon Black 2 and White 2. In the first pair of games, she had two Emolga with identical movesets, and, boy, they are extremely annoying. To start, Emolga is also part Flying-type, so now Ground-type moves can’t even touch them. Both are also equipped with Elesa’s signature move, Volt Switch, to annoyingly switch out and mess with our strategies. On top of that, they have the Static ability to paralyze and slow you down upon contact. Elesa’s two Emolga are among the strongest, non-ace Pokémon owned by any Gym Leader.

In Black 2 and White 2, Elesa replaces one of the Emolga with a Flaaffy. While she also can paralyze challengers with Static and also plays the switch game with Volt Switch, Elesa’s Flaaffy isn’t too tough to handle. However, don’t rest easy…

Elesa’s final Pokémon, Zebstrika, is an absolute monster. Just like the rest of her teammates, Zebstrika can switch out with ease via Volt Switch. But, she also boasts great coverage in Flame Charge and Pursuit. Zebstrika is very, very quick, and will most likely attack first in any given turn. If Emolga and/or Flaaffy are still in the wings, Zebstrika will likely strike first with Volt Switch before you can even leave a scratch. Speed, switching tactics, and coverage are what cement Elesa among the best of the best. 

She’s a Gym Leader and a model?!

5. Sabrina (Extremely Strong)

Saffron City Gym Leader Sabrina - Pokémon Yellow

As is the case with many video game series firsts, Pokémon Red and Blue had some prevalent issues that needed some fine-tuning. One of the big ones here was balancing out the Psychic-type. Psychic Pokémon ran rampant in the series debut. Dark-types didn’t exist yet, Bug-type moves were hilariously pathetic, and a coding error made Psychic-type immune to Ghost-type attacks (not to mention the Gengar family, the only Ghost-types in Kanto, were also part Poison and thus weak to Psychic). No NPC in the game took advantage of this like the Psychic-type Gym Leader, Sabrina. And, while Dark-type moves and Pokémon existed by the time of the remakes FireRed and LeafGreen, they were still very difficult to obtain without trading in both those games and the Let’s Go duo, plus the Ghost and Bug problems were solved. Regardless, Sabrina still can dish out a lot of pain and easily wipe the floor with your Pokémon.

Sabrina leads with Kadabra in Red and Blue, as well as their two sets of remakes, and its pre-evolution, Abra, in Yellow. Kadabra is here to slowly wear you out and drain your Power Points (PP) needed to attack. Using Recover to constantly heal, Kadabra, in Red and Blue, could also use Disable to render an attack unusable, and in Yellow, could lower accuracy with Kinesis. Sabrina’s Abra in Yellow, although it had no damaging moves, also played the accuracy game with Flash. Despite not being fully evolved, Abra and Kadabra had respectable speed, allowing them to do all sorts of infuriating things before our Pokémon could even move a muscle.

Compared to Valerie’s, Sabrina’s Mr. Mime is a formidable mid-battle obstacle. Using Barrier to sharply boost Defense (and, in FireRed and LeafGreen, using Baton Pass to switch out and pass the stat boost to another Pokémon), we learned not to judge a Pokémon by their clown-like appearance. In Red, Blue, FireRed, and LeafGreen, Sabrina has, for whatever reason, a Bug/Poison-type Venomoth. Unlike Volkner’s Ambipom and Octillery, Venomoth’s typing differing from Sabrina’s specialty doesn’t really work in her favor, but, luckily for Sabrina, this doesn’t make the battle any easier for her challengers.

The most recent remakes, Let’s Go Pikachu and Let’s Go Eevee, up the ante for our showdown with Sabrina. She adds Jynx, Hypno, and Slowbro to the mix, with each having fantastic coverage moves. This only gives Sabrina more support to center around her ace, Alakazam. With insane Special Attack, a diverse movepool, and the Synchronize Ability in FireRed and LeafGreen to pass on his ailments to your own Pokémon. Even with the type being balanced out after Red, Blue, and Yellow, Psychic-types are still very powerful, and it shows with Sabrina’s lineups.

Now that was a mind-bending battle!

4. Clair (Extremely Strong)

Blackthorn City Gym Leader Clair - Pokémon Crystal

Pokémon Gold, Silver, and Crystal are, arguably, the easiest titles in the franchise. Its remakes, Pokémon HeartGold and SoulSilver, fixed the difficulty level, but is still manageable for rookie trainers. However, even the least daunting games still have daunting challenges. Our final gym battle with Clair is a perfect example of this.

Clair is a Dragon-type Gym Leader, which, on its own, is a fantastic type. Dragons are only weak to Ice and other Dragons, and resist the core elemental types of Fire, Water, Grass, and Electric. While Clair’s gym in Blackthorn City bordered the Ice Cave, where a few different Ice-types could be found, having one on your team didn’t make this battle any easier. Delibird is terrible all-around, Sneasel and Jynx are extremely frail, and Swinub’s secondary Ground-typing made it susceptible to a few of Clair’s coverage options.

In the original Johto trio, Clair has three Dragonair (two in the remakes). Their movepools are nearly identical, but can be distinguished by their final move. If you have an Ice-type move on a Water Pokémon, one of the Dragonair can counter with Thunderbolt, or, in the remake, another Dragonair can work around Ice-types with Fire Blast. In the remakes, the third Dragonair is replaced with a Gyarados, who is not even a Dragon-type. As a Water/Flying-type, you can easily fry this thing with an Electric Pokémon, but, compared to other regions, Johto’s selection of Electric-types is limited. 

If you manage to take down Clair’s first three Pokémon, don’t assume you're out of the woods quite yet! Her Kingdra is a force to be reckoned with, rivaling the Elite Four’s Pokémon in difficulty levels. Also being the Water-type meant that Kingdra took neutral damage from Ice attacks and was only weak to Dragon (remember, Fairies  didn’t exist yet). Like Sabrina’s Kadabra, Clair’s ace can aggravate your Pokémon by lowering accuracy with SmokeScreen, and follow up with powerful Surfs, Hydro Pumps, Dragon Pulses, and Hyper Beams. As the first Dragon-type Gym Leader in the series, Clair shows us why Dragons are so lethal. 

Well said, Clair.
 

3. Raihan (Brutally Strong)

Hammerlocke Gym Leader Raihan - Pokémon Sword and Shield

While he is listed as Dragon-type Gym Leader, it would be more appropriate to say that Raihan specializes in the Sandstorm weather mechanic than in a specific type. Just like Tate and Liza, the battle with Galar’s final Gym Leader is a Double Battle. And we all know what that means… strategy is vital to success.

Raihan’s two non-Dragons, Gigalith and Sandaconda, are here to set up Sandstorm. While this weather condition doesn’t aid Raihan’s team offensively, the damage from the debris will slowly whittle away at your Pokémon that aren’t of the Ground, Rock, or Steel-types. Outside of the setup, the pure Rock-type Gigalith can dish out serious pain with high Attack, and weather through (no pun intended) most hits with insane Defense. The pure Ground-type Sandaconda can cover his weaknesses to Grass and Ice with Fire Fang, use Protect to stall, and paralyze foes with Glare. His next Pokémon, Flygon, gives Raihan’s team some much needed speed, while still showcasing strong offense. Not to mention he has great coverage attacks as well. Even if you get past those three, you’ll still have a near insurmountable Pokémon on your way to victory…

Pokémon Sword and Shield introduced the Dynamax and Gigantimax phenomena, where Pokémon would grow in size and be able to use Max Moves. Some Pokémon could simply Dynamax, while others had unique Gigantimax forms with signature G-Max moves to boot. Raihan’s ace, Duraludon, is a very scary opponent, especially as a Gigantimax Pokémon. Once in his Gigantimax form, Duraludon could upgrade his Dragon attack, Breaking Swipe, to G-Max Depletion. Doubling in power, this attack will also reduce the PP of the last move your Pokémon used. When upgraded, the Steel/Dragon-type towers above many other Pokémon as one of the most formidable in all of the Pokémon world. Although Dynamax and Gigantimax Pokémon are reverted to normal after three turns, you’d better say your prayers that Raihan’s Duraludon won’t sweep your team within that time.     

Yeah, dream on, pretty boy.

2. Whitney (Brutally Strong)

Goldenrod City Gym Leader Whitney - Pokémon HeartGold and SoulSilver

One word: Miltank… okay but in all seriousness, our third Johto gym battle gave many young players, including myself, nightmares of never getting past that evil, notorious cow. For a third Gym Leader, Whitney is outright unfair in terms of difficulty. Considering this is Gold, Silver, Crystal, and their remakes we’re discussing, that says a lot. She only has two Pokémon in her arsenal, but her ace alone is more than enough to cement her as the runner-up of the toughest Gym Leaders.

Whitney begins with a Clefairy. Battling this not-yet-Fairy-type is a cakewalk, as long as she doesn’t get lucky with Metronome. However, when she sends out her Miltank, have mercy on your soul…

Many Pokémon fans compare Whitney’s Miltank to Satan himself, and justifiably so. Miltank’s movepool includes Attract, to infatuate any opposing Pokémon of the opposite gender, and Milk Drink to restore HP. She can also cause foes to flinch with Stomp, and build up insane power with Rollout. We had very few options for Fighting-types at this point in the game, and having a Ghost couldn’t protect you from Rollout. Even worse, in HeartGold and SoulSilver, Miltank had the Scrappy ability, which enabled the Normal-typed Stomp to actually land on a Ghost-type. Oh yes, I also should mention that, once you win, Whitney cries and refuses to hand over the badge until she stops throwing a tantrum, which only fills me with more rage. For a Normal-type Gym Leader who’s faced third in their region, Whitney’s power is far from normal.

Love hurts… literally.
 

1. Juan (The Strongest)

Sootopolis City Gym Leader Juan - Pokémon Emerald

Oh boy. The final gym of Hoenn is tough enough in Pokémon Ruby and Sapphire when facing off with Wallace. But, in Pokémon Emerald, Wallace is now champion, and his mentor, Juan has taken the reins of the Sootopolis City Gym. Although I defeated Juan on my first try during my playthrough of Emerald, the battle took a whopping forty-five minutes. Safe to say, Wallace learned from the best.

Juan leads off with a Luvdisc, and, oh my goodness, this thing is beyond annoying. Luvdisc’s only decent stat is Speed, but that’s all she needs. This Water-type will outspeed almost anything, using Sweet Kiss to sow confusion and Attract to immobilize foes. If your Pokémon can’t land an attack, you’re in for it. The lead Pokémon of any major battle is meant to either set up or annoy. Luvdisc does the latter, making her lackluster offense and defense meaningless. 

The meat of Juan’s team also has a wide range of strategies to take control of the battle. His Whiscash and Sealeo have the secondary typings of Ground and Ice respectively. So, if you thought you could sweep this battle with just a Grass-type or just an Electric-type, guess again. Whiscash can also use Rain Dance to power up Water-type attacks, while Sealeo can paralyze with Body Slam or lock your Pokémon into using only the last move selected with Encore. Juan’s Crawdaunt doesn’t provide the same coverage as Whiscash or Sealeo, but the high critical hit chances of Crabhammer can really sting, especially if it’s raining. 

Eventually, you’ll be face-to-face with Juan’s Kingdra, who makes Clair’s Kingdra look like an absolute joke. Again, Kingdra’s only weakness is to other Dragons. We have two options for Dragon-types at this point in the game in Flygon and Altaria, but neither of them stand a chance against Kingdra’s quadruple-damaging Ice Beam. Kingdra’s main tactic involves Double Team and Rest. By using Double Team enough times, landing an attack will be near impossible, and, if you do manage to deal considerable damage, Kingdra can use Rest and undo your progress. I should also mention that, if Whiscash’s Rain Dance is still on the field, Kingdra’s Swift Swim ability makes him even faster than usual. My bout with Kingdra during that first Emerald run went on for nearly half-an-hour: Kingdra had exhausted all of his PP by the end of the fray. Although Kingdra is clearly Juan’s ace, the rest of his squad is also very capable of getting you all washed up, which is why I rank him as the toughest Gym Leader in Pokémon history.

AAAAAAAAGGGGHHHH!

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