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Which Region has the Hardest Set of Gym Leaders?

The game I found the hardest in terms of Gym Leaders, would've been Pokemon Gold/Silver when you fight Blue. His team are all tanks and deal a ton of damage. You basically need an entire team with higher levels than his team to win really. (Gen 2 at least).
Hoenn. Ruby and saphire. Roxanne was little difficult. Brawly was a little more so. I had the most challenge with Flannery and Winona. Even the others had their strengths.
I would agree with ThAtGuY101 that Hoenn would have been the most difficult. If for no other reason than the order of gyms against most of the starter type advantages as well as the fabled Winona who was considered so difficult she holds a spot in the Hall of Fame for most.
Yeah, I actually agree with Hoenn (and not just because Ruby was my first game and so for the first bit I only ever played with my starter (Blaziken)). Even after I learned about type match-ups and such, Hoenn just had some of the most difficult Gym Leaders that were really able to take on even Pokemon that should be strong against them. Every region has its notable Difficult gyms, but Hoenn consistently had tough challenges with its Gyms.

Deleted member 284192

I'd agree on Hoenn. Especially considering an early gym like Brawley's that doesn't give you many places to train up your Pokemon aside from the trainers within the gym. I also think of Norman's gym. All the trainers use different strategies whether their pokemon have held items like berries or they are using stat boost items. The Slakings can be scary too.
Hardest Gym leaders for me were Generation 3 and 2. Whitneys irritating milktank surely drained my pokemon and made me grind for ages. And Normans Slaking, Omg if truant wasnt a thing I would consider that thing a beast of the Netherworld!
I think maybe one of the first three generations. Kanto: Freaking sabrina was like almost impossible in yellow, she had and abra, kadabra and alakazam all at level 50! Johto: Whitney's miltank is a pushover because 1: its move set. Miltank has milk drink (when whitney is out of potions) rollout which can flinch if moved first and, ok i can't talk about this dumb gym leader anymore. Hoenn: Norman has two slaking in both ruby and sapphire but in emerald norman had a pretty much useless spinda but a stupid linoone with belly drum. Oh, did i mention his slaking have facade AND counter?
If I am not mistaken Hoenn was considered the most difficult of all generations entirely due to the fact that the first Gym through third Gym more or less destroyed you no matter what Starter Pokemon you had chosen. As well as the fact Winona had a legitimate "NERF" from the games that shipped at launch, and those that shipped about 6-Months Afterward; the original cartridges to this day sell for more since that adorable Miltank kept on Rolling, and Rolling, and Rolling the Sanity away from Players due to the shear about of damage output and speed.

This being said, my personal opinion, is that the Kanto Gyms were the hardest as this was the first generation, before most people knew what made a proper "Gym Team" and people went in with their favorites. It also followed the Hoenn Model of a Rock Starter (Required Water) and then immediately afterward Water Gym (Required Grass Type) and then Electric Gym (Roasted your powered up Starter and Flying). My only reason for maybe doubting this choice is that the later gyms were more or less a cakewalk once your teams were sufficiently powered up.

Or you were rocking that beautiful Level 251 Misingno, none others would do the same amount of chaotic damage that taught the world the nature of IVs and how the numbers would "Roll Over" from absurdly high to non-existent due to variables we could not see or define... I miss the days of Pokemon Go where all you had was an appraisal and had to apply logic to the quotes to guess at the IV of the given Pokemon!
Probably the original games because of the limited movepools. They just...were a thing I found pretty difficult to go through.