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Ten of the Toughest Gym Leaders to Tangle With

If you want to be the very best, you have to beat the very best. Throughout the Pokémon universe, you’ve gone head-to-head with sensational gym leaders ensconced in their respective towns, cities, villes, and bergs. Sometimes you walk away victorious, a lambent badge in hand and blossoming confidence within. Other times you’re forced to limp back to the local Pokémon Center with your decimated team and fractured pride. 

You win some, you lose some. It’s the life of a Pokémon Master in training. 

Gym Leaders
Courtesy of Nintendosoup

But not all gym leaders are created equal. While each of the city sovereigns provided a level of difficulty in their own right, a few stood out above the rest. To honor those who pushed our teams to the brink, I put together a list of ten (and two honorable mention) gym leaders I believe to be the cream of the crop. Let’s dive in.

Honorable mentions:

Type: Normal
Region: Unova

Gym Leaders
All images courtesy of Bulbapedia

There are only a few Normal-type gym leaders in Pokémon, and even though this type lacks the star power of an Electric or Dragon-type, they only have one legitimate weakness and the capacity for a pulverizing moveset. Simply put, it ain’t always easy conquering Normal-type gym leaders.

Gen V’s Lenora, an archaeologist by trade, fits the bill as not only one of the strongest Normal-type leaders, but one of the best overall. There are so many heavy-hitters amongst the gym leader community, though, so she just misses out on the top ten.

Lenora’s speedy Herdier and Watchog use Roar and Mean Look to dictate which Pokémon are present in battle, making her exceptionally skilled in the art of controlling the match. She’s cunning and meticulous and gives you a frustratingly tough battle. She’s good, even great, but she doesn’t quite crack the list. 

Tate & Liza
Type: Psychic
Region: Hoenn

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Hoenn was the first generation to bring double battles, and with them, an entirely new dynamic to gameplay. The gym leader tandem of Tate & Liza battle with only one Rock/Psychic Pokémon per sibling which is, in my opinion, underwhelming. 

Getting to Mossdeep City requires the HM Surf —a move that can wipe out Rock-types with ease. Combine susceptibility, a limited team, and the Mossdeep gym being late in the game (7th badge), and you can walk in and out of this gym in no time flat. 

To some, this may seem too low of a ranking. Can they be a hassle? Sure. Can you get in and out with a badge quickly? Absolutely. But if a gym can be doused with a few drops of water and end in seconds, I can’t let them into the top ten. This mention is for all you Tate & Liza fans.

Now let’s get into the real honchos.

10. Valerie

Type: Fairy
Region: Kalos

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Valerie enters the chat being the first gym leader trainers encounter who uses the new breed of Pokemon known as Fairy-type. A fashionista originally from Johto, Valerie brings her love for all things beautiful and mastery of the newfound type to Kalos. 

Fairy-type Pokemon were introduced to the franchise as a new element capable of taking down the historically powerful Dragon-type Pokémon. In the past, only Ice and other Dragon Pokemon could get the better of the drake species, but with the addition of Fairy-types, the playing field is leveled a bit more. 

At the same time, Fairy-types are only susceptible to super-effective attacks from Poison and Steel-types. Couple an unfamiliarity factor with her formidable team of Mr. Mime, Mawile, and new Eevee evolution Sylveon, and Valerie more than deserves a spot on this list. You have to respect a formidable trailblazer.

9. Brock

Type: Rock
Region: Kanto

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From foe to friend, Brock remains one of the integral characters in the Pokemon franchise. As your character’s very first gym opponent, Brock was the jumping-off point for all of us on our way to becoming Champion. But just because he was the first of eight leaders doesn’t mean he’s a slouch.

Brock offered a legitimate challenge as the very first gym leader. He boasts a tough team of a Lv.12 Geodude and Lv.14 Onix, with both rocking a high defense. The Onix is even armed with Screech, which widens the chasm between its defense and yours—as if the discrepancy wasn’t already overwhelming. Over and over, you’re forced to throw out a barrage of attacks you’re not entirely confident will be effective. 

Luckily, trainers have early access to the Fighting-type Mankey, which is super-effective against Brock’s Rock/Ground types. Squirtle and Bulbasaur also have type advantages, so if you chose either of them, his relatively high-level-for-early-game Pokémon gave us a chance to show our mettle. If you picked Charmander, though? You’re in for a rough fight.

If we had only had Nurse Joy to accompany us as we took on the Pewter City Powerhouse, it may have been a simpler battle. Unfortunately, it wasn’t in the cards, so our first gym badge was difficult to obtain. 

8. Lt. Surge

Type: Electric
Region: Kanto

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Back in the day, the Vermillion City military man with electricity at his fingertips gave us a good run for our money. Lt. Surge was the first leader we didn’t have an advantage over with any of the available starters. On top of that, Electric-types are tied with Normal-types for having the least amount of weaknesses. And who could forget the troublesome search for switches it took just to open the gates to battle him? 

The lieutenant sported a stout team of Voltorb, Pikachu, and Raichu, and the latter was armed with the move Thunderbolt. Unless you made a decision to roll with Geodude or Onix in Mt. Moon, there were slim pickings as far as Ground-type availability.

To take it to Lt. Surge, our best bet was snagging a Sandshrew after leaving Mt. Moon or wandering around Diglett Cave to find one of its inhabitants before battling for a Thunder Badge. If neither was an option, then it’s a good ol’ war of attrition against a squad that could tear you down, paralyze you, or simply drive lightning bolts into your team without a second thought. We salute you, Lieutenant. 

7. Fantina

Type: Ghost
Region: Sinnoh

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Hailing from the Hearthome Gym is Ghost-type leader, Fantina. To many, Fantina is considered one of if not the single hardest challenges in Platinum, Diamond, and Pearl. This should come as no surprise to those who’ve played the installments. You know as well as I: she was a menace.

As the fifth gym leader in Diamond and Pearl (I won’t get into the injustice of making Fantina the third gym in Platinum), Fantina battles with Drifblim, Gengar, and Mismagius. Not only are all three fully evolved, they’re also over-leveled at this point in the game. 

As if the battle wasn’t hard enough, a reliable Ghost or Dark-type was hard to come by at this stage of the game, basically nullifying the opportunity for type advantages. In most cases, this test came down to how long you were willing to meander through wild areas and keep beating up on local Pokemon to level up high enough to overpower her team of devastating apparitions. 

6. Norman

Type: Normal
Region: Hoenn

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Ah yes, dear old Dad makes the cut. Norman is first and foremost known as the father of your character in Ruby and Sapphire. He moves your family into a new home and then proceeds to leave and never come back—thanks, Dad. Instead, he spends his time brawling trainers in the Petalburg City Gym and parenting from afar. Cool. 

Make no mistake, while he may not win Father of the Year, he’s honed his skills as a ferocious gym leader with an iconic set of Pokemon. Norman has become one of Hoenn’s most difficult trainers with the help of his team of Herculean sloth Pokémon (queue ironic scoff) made up of one Vigoroth and two Slakings.While Vigoroth is a relentless beast, Norman’s Slakings are nothing less than titans, even with their Truant natures.

Unfortunately, Normal-types are somewhat looked down upon in the community because they don’t possess the flash or pizazz you find with Dragon or Electric-types. With Pops flying the Normal-type flag, they get more of the respect they deserve.

5. Sabrina

Type: Psychic
Region: Kanto

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Sabrina comes in at a reputable no. 5 on my list, but her ranking goes beyond her powerful team. When we encounter Sabrina in Gen I, it comes on the heels of a not-so-easy battle with Celadon City’s Erika. Between the time you acquire the Rainbow Badge and enter Saffron City’s gym, there isn’t much opportunity for storyline training. That reality makes facing her that much more difficult.

In a funny twist, Saffron City is the location of the Fighting Dojo, where you can pick up either a Hitmonchan or Hitmonlee—both of whom stand no chance against Sabrina’s psychic squad. Her team consists of high-level specialists including a Kadabra, Mr. Mime, Venemoth, and a metaphysical Alakazam.

Unfortunately, there aren’t many dependable options (Dark-types weren’t introduced until Generation II) to counter Psychic-types in Kanto. Add that to a generally weak class of Bug-types (not judging, but how many of us truly roll with a Bug-type this far into the game?) and it makes for a down-to-the-wire fight for Saffron supremacy.

The placement of Sabrina in the gym leader hierarchy made for a tough roadblock in our journey. Psychic-types expose several popular types like Poison and Fighting, and Sabrina was a menace in a period of vulnerability. I can recall a few times when I speedily button mashed only to come up short and have to retrace my steps in that house of horrors she calls a gym. 

4. Giovanni

Type: Ground
Region: Kanto

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The Man in the Shadows. The Leader of Team Rocket. The zenith of our scourge on gym battles and the final step before heading to Indigo Plateau. The heinous, villainous, and nefarious Giovanni. What a guy, huh?

Unlike the other gym leaders, we battle Giovanni twice before ever reaching his gym in Viridian City, and each time gets progressively more difficult. His final team of Rhyhorn, Dugtrio, Nidoqueen, Nidoking, and Rhydon are a force to be reckoned with even though there are plenty of excellent options to provide advantages over Ground-types.

Nidoqueen and Nidoking sport Poison-type moves and can be real problems for a team on the precipice of championship. His final Pokemon, Rhydon, uses the move Fissure—your reward once you’ve eked out a victory—which one-hit KO’s a Pokémon if it lands. Even though it’s a move with a low chance of landing, it still makes us hold our breath when used. 

Upon reaching Giovanni, your team should be pretty well-set for the upcoming Pokémon League. At the same time, the eighth gym badge isn’t so easy to earn with Giovanni’s powerhouse team looming near the finish line. 

3. Clair

Type: Dragon
Region: Johto

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We’ve officially entered Dragon territory. Known as the “Blessed User of Dragon Pokémon,” Clair descends from a famous drake-wielding family which gave Pokémon trainers rousing battles in Gen I. Their reign continues with Clair taking up the helm as the eighth and final gym leader in Gen II.

The self-proclaimed “world’s best dragon master,” Clair is as poised in battle as any other apex trainers you’ll come across. She wields an outstandingly strong trio of Dragonairs along with an overpowering Kingdra. Up to this point, there are very few Dragon-types available, so your best bet is to battle with Pokemon equipped with Ice Beam or Blizzard—even the recently acquired Icy Wind, courtesy of Pryce, might stand a chance.

Unfortunately, it might not be enough. One of her Dragonairs knows Thunderbolt, meaning any Water-type to whom you taught an Ice-type move remains vulnerable. At the same time, if you managed to acquire your own Dragon-type, another one of her Dragonairs comes prepared with Ice Beam, which can topple your team’s dragon. 

When you do manage to get by her Dragonairs, the battle only gets harder. If you’re reading this, you understand just how dynamic her Kingdra is. Along with high-powered moves including Surf and Dragonbreath, Kingdra will diminish your accuracy with Smokescreen, giving it time to prepare for the decimating move Hyper Beam.

It takes throwing everything AND the kitchen sink to beat Clair. Her team can paralyze you, deal loads of damage, and wipe you out with ease. I advise having several Hyper Potions, Revives, and Full Heals before facing the original Mother of Dragons. 

2. Whitney

Type: Normal
Region: Johto

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I can almost hear your moans and groans just at the sight of “The Incredibly Pretty Girl,” Whitney. While new to the block, she attracted (multiple puns intended) enough attention from the Pokémon League to appoint her to a Gym Leader position. You know as well as I that this battle is forever ingrained in the minds of trainers.

The Clefairy maze Whitney has you traverse to get to her encapsulates everything about her. It’s pink, laden with delicate flowers and shrubbery, and is home to trainers equally as innocent in appearance. Ironically, this is merely a facade when it comes to taking on Whitney herself. 

Whitney draws out the battle with moves like Mimic, Attract, and Encore, slowly manipulating your team into basically beating itself. Getting by the leading Clefairy proved difficult at times with Metronome as a wildcard move, but once completed, Miltank—the biped livestock with an alarmingly large udder,  admirable stats, and high level—was the main event.

It would use Attract to put your Pokemon under a seemingly unbreakable love spell. Now immobilized by affection, Miltank would beat your team down with Rollout and revitalize its health meter with Milk Drink. Around and around you went on this peach-colored merry-go-round, being viciously attacked by a giant pink cow. How embarrassing. 

Numerous times I was thwarted by Whitney’s false cuties and sent back to the Pokémon Center completely deflated. After finally beating her, she throws a temper tantrum and runs off crying, which, in a sort of disgraceful way, is vindicating. The most effective way to face Whitney was to acquire a Machop by trade in Goldenrod City and Karate Chop your way to victory. Even then, her strategy of playing with your Pokémon’s emotions sometimes couldn’t do the trick. Whitney is testament to the adage, “Never judge a book by its cover.”

1. Blue

Type: Destruction
Region: Your nightmares

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At last, we’ve come to the top spot. Blue, Gary, Professor Oak’s Grandson, Rival, Jerk, whatever you want to call him, this arrogant boychild is an unruly gym leader you love to hate. For years, he brought the smoke that pushed your team to the brink of blackout. And his time as the Viridian City Gym Leader may be the biggest mettle test across generations of gym battles.

Getting by Blue’s high-octane team of Pokémon with no particular type theme was never looked forward to by any trainer. One after another, he blasts you with brutal physical attacks and otherworldly special attacks all while giving you the unrelenting verbal business. Tauros, Alakazam, Gyarados, Exeggutor, Aerodactyl, and Charizard, all studs in their own right, relentlessly lay siege upon your team with a blitzkrieg of assaults.

At any point, your Pokémon could fall victim to the one-hit KO power of his crew. He also deployed a crafty strategy where he would send out his team in no specific order, making it troublesome to find the right matchup ahead of time. Even with your team trained well enough to be on the precipice of master status, Blue is an ultimate test that will have you questioning whether or not you’re truly ready for the big leagues. 

In the Viridian City gym, it’s not always been an easy feat to emerge triumphantly. Blue is considered a wunderkind for a reason. But it doesn’t matter what game, in any generation: delivering the crushing blow to Blue’s final Pokémon is as fulfilling as becoming Pokémon League Champion. 

There you have it. In all my years as a Pokémon Trainer, I found the aforementioned leaders made for the most arduous battles. But I want to know your thoughts. Drop some comments below and let me know who you believe should be on the list. Until then, like Blue says, “Smell ya later!”

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