Thanks, Satan.

 

Kanto because I'm one of those fossilized retards who declares all other generations of pokemon to be GAY (barring certain individuals).

This was the team from my first successful nuzlocke run and I usually recreate it now when I boot up the ol' fire red. I've played other teams and I've played better teams but this is my team, dammit

1. Bulbasaur (Ivysaur is acceptable comprimise between power and aesthetics but NEVER Venusaur omg)
2. Primeape
3. Crobat*
4. Marrowak
5. Kingler
6. Ninetales

Otherwise, grass gym - Kanto or Johto
1. Ivysaur
2. Bulbasaur
3. Chikorita
4. Vileplume
5. Victreebel
6. Bellossom

And before you mock it let me remind you it's a grass gym so I'm giving out badges like they were Halloween candy, anyway.

 

Gonna go with something a bit different. How about an early gym? Let's go with Dark typing and the second or third gym. Arena is a pretty standard battle field, but trainers who have done their homework will know that something about the arena is making the speed of the pokemon battling within very... strange (trick room effect). The trainer can switch pokemon at will, but it is a 3 on 3 battle. My pokemon must remain out until it faints or wins.

I would use 3 Pokemon:

Carvanha LvL 22 would be my lead. It doesn't take advantage of the trick room, being fast, but aqua jet could ruin some strategies of trainers' who are privy to the trick room.

My second pokemon would be a Houndour LvL 22. Pretty standard fare, but trainers who chose a fire type will have some issues if they aren't learned about Flash Fire.

My ace would be a Deino LvL 25, to take maximum advantage of the trick room. It is in the possession of a rare artefact that can bring out an unevolved pokemon's full potential. (Eviolite)

So, a pretty tough disadvantage to trainers who chose the fire or grass starter and a slight buff to whoever chose the water one. And Deino could be a real asshole in a low level gym. Trainers who win would get the Treachery Badge.

 

My choice would be bug type, which surprisingly has quite a few good options to pick from.

The team would consist of:

Pinsir
Heracross
Galvantula
Volcarona
Scizor
(And an optional Shedinja at the end for the lulz)

 

I think I'd go with a Dark type gym. 7th gen, so Alola gets Gyms or I'm a Kahuna, whichever works.

I'd go with a team of 6, with the following pokemon:

Scrafty
Hydreigon
Tyranitar(Mega if allowed)
Alolan Persian(Z-crystal for dark type so I can use Z-parting shot)
Alolan Muk
Houndoom

The gym would alternate between complete darkness and flashes of strobolights every 30 seconds, and have a ton of background noise to make it hard giving commands to your pokemon. Beating the gym would give you a Discord badge, which would be a black badge with rough edges and a single note drawn with silver in the middle.

 

Assuming I've proven myself as a true master and gotten tons of sponsors and shit willing to pay for my Gym's creation, I think I would start an Eeveelution Gym. 7 gens in and Eevee is still prolly the cutest little fucker in the pokeworld and I want tons of them. I WANT ALL OF THEM. I would spend my free time evolving Eevees in different conditions and hunting down rare stones and metals to expose them to in the hopes of discovering the next Eeveelution to introduce to the world.

Anyway, due to the sheer OPness of Wish/Protect/Toxic stalling, I think I would probably be an end of the journey sort of gym leader like Gio; a final check on regional trainers to make sure they really do know their stuff before they head off to championships and the like. If you don't have all the badges from the rest of the region, I'm not fighting you.

My gym would be an octagon of different landscape sections, with proper conductor environments for each Eeveelution, and a wide meadow at the center.

The fight would be a greulling nine pokemon battle:

Jolteon with VoltSwitch / Thunderbolt / Roar / HP:Ice (# Life Orb)
Vaporeon with Scald / Ice Beam / Wish / Protect (# Leftovers)
Flareon with Flame Charge / Rest / Sleep Talk / Facade (# Toxic Orb)
Umbreon with Toxic / Moonlight / Protect / Foul Play (# Dark Z Crystal)
Sylveon with Toxic / Wish / Protect / Draining Kiss (# Rocky Helmet)
Espeon with Psyshock / Light Screen / Reflect / Dazzling Gleam (# Light Clay)
Leafeon with Leaf Blade / Synthesis / Wish / Dig (# Resist Berry)
Glaceon with Ice Beam / Substitute / Wish / HP:Ground (# Leftovers)
Eevee with Return / Toxic / HP: Psychic / Wish (# Eevite)

If you beat me, you get the Diversity badge, which would be a nine pointed star with each point a different color