Hakone League in order of relative difficulty

Gym Leaders:


Electric: Lilac City
Zap Cannon
Youngest of the Cannon Family. Fights on a floor that transmits electric attacks to everyone on it. Surprisingly tough for as nerdy as he looks, and as soft as his day job is.

Grass: Pine Haven
Kalipso Pevensie
Bluh bluh huge hippie. No particular gimmick, though if you choose to have trainer interference, becomes one of the hardest gyms in the region.

Bug: Olive City
Mr. and Mrs. Webb
Octogenarians competing every year for oldest gym leader. Tends to go very easy on people they find entertaining, but surprisingly harsh on "rude punks". Easily mistaken for anyone's grandparents.

Water: Coral's Rest
Hydro Cannon
Second youngest of the Cannon Family. Has a variety of challenges for his badge, only some of which actually involve fighting. Easily distracted and sort of lazy.

Ice: Snowy Peaks
Tom. No other names given or known.
Muscular man with questionably legal practices and no sense of volume control. Almost too friendly sometimes. Offers as many rematches as anyone can take, even going so far as to have people spend the night.

Poison: Mulberry Town
James Kojiro
Former Team Rocket member that quit in disgust after a great number of years of service along with a certain two others. His former partner disappeared, but he quickly used his inheritance on getting a lighter jail sentence and an old castle. No particular tricks or quirks if challenged in the gym, but he isn't always IN the gym...

Dragon: no actual town
Danny "Rock" Snipes
Famous hunter who spends most of his time in particularly untamed stretches of wilderness. Badges go to people who have overcome great trials involving nature or wild pokemon while he's watching. As a winning smile but, according to some reports, a losing personality.

Fire: Mount Scarlet
Ignatius Farrence
Second time as gym leader of the town, having taken the position back after the sudden and still unexplained death of his son. Hasn't taken many challenges as of late, having the gym doors locked more often than not. Reports of bone-chilling sounds coming from the building at night, but everyone's just assumed he's still mourning.

Ground: Auburn City
Scorpio Hardmeat
Looks and acts like an extra on the set of a cheesy action movie. Very sensitive about his name. Forces challenging pokemon to try to attack with weapons rather than any of their natural abilities.

Flying: Altaria Islands
Lizzie Jones
A bubbly self-proclaimed ninja whose gym building is only just for show. Fights take place across the whole town over an entire day, as much a test of endurance as it is skill. Smarter than she looks (and acts), supposedly.

Fighting: Rosewood City
Alicia Rosewood
More like a personal trainer than a gym leader in most fights. Gives badges based not necessarily on winning or losing, but on how well the trainer did when it ends. Any sort of fight can be found at almost any hour in the gym itself.

Ghost: Old Gold Town
Granny Gotva
Long since known as the pillar of the quiet town's community, only recently having taken up the position even though she's basically filled the role for ages. After the power plant incident, hasn't been seen in town much at all and took up residence in the woods. Doesn't even require a fight to earn the badge, but the alternative is sometimes worse.

Psychic: Salmon Springs
Samantha Atana
Cool, mysterious local personality. Gym doubles as an inn, capitalizing on the town's hot springs. Has shown a great variety of psychic powers, and themes her challenges around all known forms of them.

Rock: Russet Town
Cypress Siblings
Set of three children of the region's mining tycoon. All are connected to some important facet of the city. Has a great deal of variety in challenges, allowing anyone to basically choose how many fight, what the rules are, etc.

Steel: Cobalt City
Flash Cannon
Eldest of the Cannon Family. Incredibly cold and harsh on challengers, forcing them into interference fights and always going all-out. Is greatly concerned for the city, and spends much of his off time campaigning to clean it up.

Dark: ???
?????
Nobody actually knows who gives out the Hidden Badge, even people who have it--they say they're sworn to secrecy once they meet him/her/it.

Normal (kind of): Prism Town
Position changes frequently
Holds a weekly tournament of anyone that dares to sign up. The winner faces the current gym leader for their badge... And their position. There have been occasional long periods of leadership, but everyone is dethroned eventually.


Elite Four:

Spike Cannon
Fighting (Ostensibly)
Second eldest of the Cannon Family. Wild and careless to the point where it's a wonder how he actually got into the position, let alone beat all his brothers to it.

"King Arthur"
Flying
Flamboyant actor, uses his stage name for everything. Real name kept a closely-guarded secret. Is a confirmed psychic, though a weak one.

Andromeda Rocket
Poison (Mostly)
Granddaughter of Giovanni Rocket himself. Abandoned the team and took a good portion of its hidden wealth away, doing something similar to James. Unlike James, however, she takes the league seriously. Too seriously, even.

Reinhard von Fraenir
DRAGON
It's in all caps because it's as much a lifestyle as a type to him. Runs a dragon ranch up in the mountains between Salmon and Scarlet. A jolly gentleman by all accounts, though one with a slight temper problem.