2nd Gen Easiest and Hardest gym leader

[J9794]

Bugsy was the easiest, flying pokes are easy to find
And the hardest is obviously Whitney, it's not like most gym leaders where even if you don't have something resistant to or supper efective against his/her type you can win, if you don't have something to take down that miltank, you'll be rollouted to death.

 

[morty123]

I didnt think Whitney was that though when i first met her. At that time i was no where near an expert, im not today either, but i know a decent amount. It just so happend i picked up a geodude on my earlier travels, so when miltank started with rollout, geodude would just tank it like a boss.

 

[kyuubi93]

Personally, the only gym leader I have any kind of trouble against is Clair. Whitney's Miltank is easy if you come prepared, trained, and with a step by step strategy. The reason too why I say Clair is mainly because of her Kingdra, it can be troubling sometimes.

 

[Ephemeral Euphoria]

Pryce was the easiest for me while it would have to be Whitney for the hardest gym leader slot due to how badly I fared against her Miltank back when I first picked up Silver.

 

[pyx]

Bugsy was pretty easy. As for the hardest gym leader, I'm gonna have to pick Whitney... that Miltank is just unholy...

That pink fur has plagued uncountable childhood memories...

 

[La Espada]

I've never had a hard time with Bugsy even if I pick Chikorita as my starter so I'd say he's the easiest. As for the hardest, I'd say Clair. Whitney's Miltank was bad enough but, Clair's Kindgra destroyed my childhood.

 

[flatline115]

Hardest: Whitney. Even when I play her today with (presumably) better knowledge of the game than I had as a kid I run into the same issue.. A lack of fighting type pokemon or a lack of trained fighting types to help me destroy the Miltank. Whilst most of the game is a breeze and I never use normal types. Whitney made my perceived weakness of them turn into respect.

Easiest: Falkner. Only gym leader to present no challenge whatsoever. He doesn't even deserve to be called a gym leader.

 

[MeetMeInUtopia]

The easiest for me was possibly Jasmine because Steelix was weak to water moves. The hardest by far had to Whitney. Miltank is one of the most over looked pokemon and she proved its usefulness

 

[CJoE]

I think Whitney is the hardest to defeat, her Milktank really annoying when it use charm...and the easiest to defeat? Erm, maybe bugsy cause most of his pokemon is grass and bug type which is weak to fire and flying type...

 

[Xebelleon]

Easy for me, is Chuck, considering Kadabra or Alakazam. Foresight two move combos against a ghost slows him down. Beat with a lot of things that resist Fight or can super effect against him over the years.

Hard seems to be Morty in recent runs. Muscle for Whitney is easy enough. But Ghost hitters that can cope with a fast Gengar Hypnosis are tricky to find. And having a slower Bug or Kadabra can be annoying.

 

[ShinyUmbreon189]

I'm playing through Crystal again right now and out of the first 7 gym leaders I haven't had any really hard gym leaders except for Whitney.
Faulkner and Bugsy was easy with the Cyndaquil and Pidgey line while Pidgeotto was helpful with Morty. Sand-Attack got me lucky with Morty's Gengar so I was able to easily defeat it with my level 27 Pidgeotto, Pidgeotto basically swept his team. I lost to Whitney because I was at a type disadvantage having Quilava and Pidgeotto vs Miltank with Rollout.
The second time I started with Quilava so I got 2 Sand-Attack's in giving me the upperhand.
Every other gym leader has been a breeze so far but I got Lapras so Clair shouldn't be a problem; but then again there's that lvl 40 Kingdra.

In the past depending on the starter (and who I used on my team) determined which gym leader was hardest.

Chikorita: Either Bugsy, Morty, or Whitney (Chikorita line was the weakest link for me.)

Cyndaquil: Whitney. I never really had a problem using Typhlosion's line.

Totodile: Whitney or Clair

So for me, the hardest gym leader has been Whitney.

 

[Synerjee]

Really, who on earth needs to even ask who the hardest Gym Leader of GSC is?? Whitney and her freaking Stomping Rollout-ing Milk Drinking MILTANK. Period.

As for easiest Gym Leader, I believe it has to be Bugsy. I've always had a Fire or a Flying-type on hand when I reached that point in the game, so it was always pretty easy to knock down all those Bug-types without too much of a struggle.

 

[HollyYoshi]

Easiest? I found Pryce to be pretty simple to take out.

Hardest? Do I even have to say it? Whitney. Just... that Miltank will pretty much massacre all your Pokemon if you're not careful.