5th Gen Which gym leader was toughest?

I had a pretty tough time going up against Cilan; he was the first gym leader, and I wasn't all that prepared. If it were Chili or Cress, then I would've had some hard time battling them, too, since they're all more or less the same. d: In Black 2, it was Cheren. Roxie was pretty difficult, too.
 
I had a lot of trouble with Elesa. I had no ground types because I didn't care for any of the available ones to catch at that point in the game, and Emolga terrorized me with Double Team. I'd say it took me three or four tries to finally defeat her. After her, I'd say Roxie. Poison is an extremely annoying type, that's for sure.
 
For B/W I'd say Elesa, especially her Emolga duo who love spamming Double Team plus your only shot at hitting them super-effectively at that point is a Rock-type attack, thankfully Rock Tomb is easily available at that point, and the Speed lowering effect can give you an edge.

In B2/W2 it's definitely Cheren with his whole Work Up strategy, once he gets the Attack boosts going there's very little to do to counter him so you have no choice but to watch your hapless Pokemon get ripped by his Lillipup, which is a great definition of a "cute bruiser". He's probably the hardest first Gym in the entire series if my statement means it.
 
Elesa was quite challenging! Other than her..none of the other gym leaders were that much of a challenge to be honest. Even in B2W2, Roxie and Cheren weren't particularly hard. ;;
 
If you fail to take it out quickly, Cheren's Lillipup will cause quite an issue due to Tackle's decent power and Work Up's attack boost.

I never really found any of the Gym Leader's truly difficult in Gen V. I only ever really struggled with the first Gym Leader in White due to a lack of good Pokemon and/or Experience Grinding opportunities.
 
In White, Clay's Excadrill game me a tough time because I had no attack types that it was weak against. After using Hone Claws once, it would just sweep through my entire team... Clay's Hyper Potion didn't help my situation either. I managed to beat him after training for a bit at the route that goes to Chargestone Cave (Route 6 if I remember correctly)

In White 2, Cheren was the only leader that I had trouble with. His Lillipup got pretty difficult to go up against once it used Work Up. However, it became much easier to beat him once my Riolu learned Force Palm.
 
Clay gave me the most trouble, what with his Excadrill. Even when I faced him with a Pokemon that had a type advantage, he still found a way to KO it. I've also had trouble with the Striaton trio namely because their Pokemon had a type advantage over my starter. Using the elemental monkey received in the Dreamyard didn't always help either because it would be at a lower level 'cause I didn't bother training it. (After I used it to get me the first badge, it'd be boxed forever.)
 
Gym leader Aloe, for the sole fact that I was really under leveled. Nearly every physical move that she used OHKO'd me.
 
Gym leader Aloe, for the sole fact that I was really under leveled. Nearly every physical move that she used OHKO'd me.

The hell are you talking about?? There's no Gym Leader that goes by Aloe in this game, or any of the games, as far as I know.

Anyway... the only leader that was on the challenging side would be the B/W version of Elesa, as you can't effectively combat her dual Emolga's unless you've got someone with an Ice-type attack or a Rock-type, & chances are, the player isn't going to have the former, & in the latter case, most that do learn these moves can't outrun her Emolgas.
 
The hell are you talking about?? There's no Gym Leader that goes by Aloe in this game, or any of the games, as far as I know.

Um, Aloe is her Japanese name. I meant Lenora.
 
I would have to say that the toughest is Elesa in BW2.

Any of them can be tough if you're not prepared. Among the more notable ones in that respect are Cheren and Lenora, since they both have pokemon with moves that will demolish an unprepared team (Cheren's Lillipup's Work Up and Tackle and Lenora's Watchog's Retaliate). But if you're prepared for them, they're not particularly tough at all. And that's the case with most of them. With Elesa though - even if you are prepared, she can still be tough. Volt Switch makes it tough to keep up with her pokemon unless you've got a ground in so that Volt Switch won't work, and if you've got a ground in, it's likely that it won't have a good attack against the Emolga, and it's certain that it will be so slow that it's going to take a lot of abuse along the way to finally winning.

I usually use a Trapinch against her, since it learns Bulldoze at level 21 and Rock Slide at level 25, so it can potentially handle her whole team, but it's so slow that it's touch and go anyway.

The only time I had a pretty easy time of it with her was when I went through once with a Dwebble and a Jolteon. Dwebble laid down Stealth Rock, then I switched in Jolteon, and it tanked the Volt Switches while her entire team beat themselves up against the Rocks.
 
In BW, I think the hardest is either Elesa or Clay since their attacks are pretty powerful. Lenora isn't THAT terrible, since you have a chance to get not only a Fighting-type at Pinwheel Forest, but Roggenrola in Wellspring Cave.

As for BW2, I think Cheren and Roxie are the hardest because early on you don't have many options against them. Although in my most recent Challenge Mode playthrough (a Wedlocke), Drayden really gave me a run for my money with his Cotton Guard Altaria.
 
Elesa was the toughest of all of the gym leaders. Her Emolga threw off my whole team, not even a ground type swept her team at all. So I had a hard time finding an alternative to get though. :s
 
Honestly, for me it was Lenora. I was insanely unprepared and thought that I could wing the battle and come out on top. Yeah... Didn't quite work that way. She completely owned me until I decided to wise up and train some more.
 
Elesa in both games. It was most probably because I don't usually catch ground types, but I've heard from some that she's still hard even with a ground type due to Emolga's immunity. Although I've gotten a bit luckier in the sequel, she's still a challenge to me. :( Roxie is also a special mention for BW2, but she was funner to battle! :d
 
Lenora was really annoying in Black, especially her Watchog and those Hypnosis.

Elesa in BW2 was challenging as well. And Clay too.
 
I would have to say that the second gym had to be the hardest, only because her AI knew how to do a really annoying combo with statuses. Elesa was also pretty tough, but then I got a Sandile and it didn't matter.

In the second one, B/W2 that is, I'd actually say the first one was pretty tough as well. I'd also say Skyla was 5% harder too, because her AI changed for the better.
 
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