Best Dark-type Master in-game?

[KarlG]

So, as everyone who's a Pokemon fan knows, there hasn't been a Dark Gym Leader before. Now the reason for that, I believe, is that GF believes the Dark type to be mysterious, slightly-evil and unique, hard to handle and requiring special skill to manage, tame and train. Then by Gen VI they realized it's become a tradition and Dark Elite trainers, with their mysterious personalities and sombre, morbid overtones are the way to go.

I for one, LOVE the Dark Masters introduced so far:

Karen - the original Queen of Darkness, with her iconic speech about choosing your favorites to use. Her Houndoom packed a punch in GSC and HGSS and I'll bet she's got her hands on a Houndoomite by now. In HGSS her team was arguably the most diverse and she could easily cripple you if you are unaware.

Sidney - the punk rocker with attitude for days and an all-out offensive battling style. His team is the most versatile and I'll remember how difficult it was to take down the Shiftry with Swagger. I've got my copy of ORAS but haven't played yet. Looking forward to his M-Absol (heard so much about it!).

Grimsley - INSANELY cool guy. First of all, he resembles a vampire. Secondly, he comes from a rich family, which fell into ruins, and later suffered from addiction and depression. How well-developed is this guy's backstory? His morbidity and gothic charm is what I love best and his team is also rather strong.

So, which Dark Master is your favourite? In an in-game battle much like the PWT, which Dark Master would win?

 

[Muur]

Grimesly is the coolest, though since he only uses 4 in his inital battle and Karen uses more non dark types than dark types, I'm gonna go with Sidney.

If they had the PWT, Idk because Karen has non dark types so would have to be ninjaed in with new Pokemon

 

[Rainami]

grimsley is the only correct answer

if only they gave him more of a role

 

[Osprey]

Grimsley. I like his talk about luck and chance, his team is pretty dangerous, and he's more classy than a Honchkrow. Karen's famous post-battle quote is a good motto for anyone who those who simply love Pokemon, but I don't really like her appearance... she looks like a sparkly diva. Sidney is memorable mostly for that creepy cock-eyed look he's got now.

 

[Vivillon]

Sidney, even if it's just because he reminds me of Legend of Zelda's Magic Beans guy in ORAS. :3

 

[GhostFingers]

Voldemo....

I mean, Karen. Nostalgia reasons.

 

[firepanda]

Sidney and Grimsley are two of my favourite E4 members. (Sorry Karen.)

I'd have to go with Sidney. Grimsley has the better ace, but I like how Sidney has colour.

 

[Felly]

Sidney for me. He just has this badass feel about him that I like.

 

[Tyrfing]

As stated previously, Grimsley is the only right option. I love his design, his talk about luck and chance, which is quite rare in a Pokemon game, honestly, and his team was the only one to give me trouble when I first played Black and White. Plus, I'm massively biased to Unova.

 

[LordSeliph]

Grimsley because he has a Scrafty

 

[KarlG]

I think a big part of it is that he can be challenged in Challenge Mode.