Karen

Karen Annabeth Umbra (born in Cerulean, KA) is a Kantonian professional Master Trainer, and leader of the Indigo Elite Four. She specializes in the Dark-type.

History
Karen was born to Annabeth Logan, a screenwriter, and Sylvester Umbra, a well-known championship boxer, in Cerulean City. At a young age, she showed a great interest in becoming a Pokemon trainer, as well as a high interest in her father's career, watching all of his title matches and being inspired by the success he maintained. However, because of his frequent absences from the house, despite the money he earned being used only for his family's sake, Karen grew to resent her father. Her mother was her only company as she refused to have friends and rashly started fights on the playground. Annabeth's sister, Katie, played the role of second mother to her during this time. During this period, she wished to specialize in Fighting-types, like her father.

The Mask of Ice
At the age of 11, Karen was kidnapped by a mysterious man calling himself the The Mask of Ice. She was seduced by the kind of power that she could control under his tutelage, and remained in his service for 5 years. During this time, she became intrigued by the newly-discovered Dark-type, for it had a weakness to her father's favorite type. She saw mastering these Pokemon as a way to master herself and become stronger.

She was partnered with Will, a Psychic Pokemon trainer that had been abducted around the same time that she had been.

Karen participated in the fight between the Mask of Ice and the PokeDex holders of Kanto and Johto, but was soundly defeated. She gave up shortly afterwards, forsakening the life she had lived for years. She returned to her mother in Cerulean.

Making up for lost time
Karen returned to having a normal life, but having lived as a criminal for years had changed her - she was now much more brash, arrogant, and seductive than before, the latter being the product of her aging. When she returned to schooling, she began dating boy after boy, eventually losing her virginity to one. Despite her frequent late nights, she was able to graduate high school with honors.

Unfortunately, Karen's mother Annabeth had been diagnosed with breast cancer with little chance to live. Karen spent the majority of her next year with her mother, forsaking her first semester at Kanto Regional University almost completely to care for her. Her father, retired now, chose to have the family spend as much time as possible together. Eventually, Annabeth passed peacefully. Karen was emotionally distraught, but was able to clear her head by returning to her old ways. She became a party girl, and nearly failed out of college her first year.

Around this time, Karen began to experiment with her sexuality, dating both men and women. During a spell of nearly all women, her father found out, and being a traditionalist, he slurred at her, causing them to have an enormous fight that saw the two of them never speaking again, even to this day.

Cleaning up her act
Her father's diatribe having sobered her up, Karen returned to her studies, where she graduated from KRU with honors. She then started major training, her ambition being to become a member of the Elite Four, a group of Master trainers whom were the final challenge for anyone capable of finishing the Indigo League Gym Challenge. She battled and fought, maintaining her use of Dark-types as a sort of rebellion against her estranged father, and eventually became an alternate for her hometown's Gym. She pushed farther, and eventually a position on the Elite Four opened. She applied, and in a very close match with the champion of the time, she was able to earn her worth and become a new member of the Elite Four. She worked harder still, eventually becoming the leader of the Elite Four after Lance, the former leader, took up the mantle of Champion.

The Takeover
When Team Rocket began their usurping of the Indigo League, Karen was one of the first to fight. She did well in the great battle, but was ultimately defeated and went into hiding with the rest of the freedom fighters. She became incredibly concerned when Morty, the leader of the Ecruteak Gym, was brainwashed by Giovanni into serving Team Rocket, and she rescued him (with some help from Blue). Karen tried to return him to his normal mindset but talking, but in a case of reverse-Stockholm's Syndrome, she began to develop feelings for him, eventually leading to the two having relations. She viewed this act as disgraceful afterwards, considering it rape because of Morty's condition.

Karen was involved in the final battle against Team Rocket, facing both Ariana and Proton. During the fight, she nearly died at the hands of Ariana's Arbok, and confessed her feeling for Cynthia before defeating Ariana. Soon afterwards, she began her search for Morty, who did not wish to be found. Karen gave her search up after hearing this and after talking to Officer Jenny, whom had an interest in Karen. The two did not last, however. Jenny broke up with Karen, saying that because the two would not be spending much time together because of her line of duty, and it would all be for the best.

Connections, New and Old
Karen began running Gym Inspections after the the attempted takeover ended. During this time, she befriended a Darkrai, much different than the other malevolent Darkrai she had met before.

Soon after, her father, Sylvester, attempted to reconcile with his daughter in public, a gesture that would drive her away instead of bring her closer. Her drunken self somehow managed to find her way to Unova where Karen awoke the next day. She explored Castelia City, accompanied by Dorian's Houndoom, Conner, staying with the Fukyose City leader Furou. The next day, to her and everyone else's surprise, Karen found out that her good friend Caitlin was not only an incredibly proficient battler, but an established member of the Unovan Elite Four. She returned home to say good bye.

The next day, after the actions of Desukaan had caused the near-fatal injury of Karen's good friend Jasmine, Karen sought the help of her friend Darkrai to finally defeat the creature. Instead, she was possessed, once again, by the evil Darkrai. She managed to maintain control of her body, though, and continued on, attempting to face the Mummified Pokemon with the power of two Darkrai. She was overwhelmed, however, by sheer numbers, and was nearly killed before Mewtwo interfered. Karen attemted to save Mewtwo, but was too late, as Gray's actions had caused him to become an infant Mewtwo.

She awoke the day after to find that an alternate-timeline version of her, Karin, had arrived in her timeline. The two met, and after discussing the amusement of their situation, regarded each other as sisters.

The Return of the Mask
Karen attempted to live her life, even with the return of The Mask of Ice. She had even attempted to move on from her love for Cynthia. The kidnapping of Green and Silver, however, as well as her own dark feelings cause by her interactions with the antagonistic Battle Frontier, caused her to break down. Chermaine spoke to her of having a family again with the Mask, and after being confronted by Lance, she resigned her post, giving it to Karin. She rejoined the Mask of Ice, and was branded the Mask Of Seduction.

Her first act under her "father" was to kidnap Cynthia, who she deluded herself into loving again. She succeeded, but was ordered by her father to return her as doing so could have endangered his plans. Karen returned her to the custody of Pearl and Platina.

Karen continued to work under the Mask, conducting reconnaissance missions. During her mental captivity, she grew close to her adoptive sisters Chermaine and Green, and was antagonistic towards her adoptive brother Keane.

During a visit to the League to speak to Lance, who she still respected, Karen confronted her sister, and the two fought. In the resulting battle, Karen unleashed her Darkrai's deadly Hypnosis and Nightmare attacks on her sister, and it was this that pushed her to insanity and uncaring. She then confessed that her infatuation with Cynthia was not love - it was hero-worship, idolization. She shed these "childish" feelings and began serving the Mask fully.

Karen and Green shared confidences, and Green confessed that she was scared of her "father" to her. It was this, as well as Chermaine nearly attacking Green out of frustration in the final battle, that caused Karen to betray their family and save Green. However, this did not come without a cost, as Karen sacrificed herself to Keane's attack - her legs were frozen and she was beaten half to death. She was rescued before reaching death by Mewtwo and Alex Cena.

Branded a Criminal
After recovering for days in Karin's apartment, Karen vowed to reconcile for her actions. She began by having Green join her on a trip to Mt. Silver's hot springs to heal her remaining wounds, much like Sabrina and Red had years before.

After speaking to Green about the nature of criminality, they decided to turn themselves in to Lorelei, the new leader of the Elite Four, whom had been searching for them. Shortly after, she was forced to let them go by the League. Karen then began to attempt redemption, speaking to Cynthia and apologizing for her sins against her, and assured her that she would no longer be seeking her affections. She briefly lent her apartment to Alex Cena and White for their trip to Johto.

She began seeing Lucian of the Sinnoh Elite Four shortly thereafter, which caused much trouble with Flint, who held a similar stance on Karen's innocence to Lorelei.

Return and Confusion
Lorelei was eventually ousted for her actions as leader of the Elite Four, and Karen, along with her sister Karin, returned to their post as leaders of the Indigo Elite Four.

Karen began taking interest in Shion Kitakami, a recently outed lesbian, who had spoken to her before. She sought the permission of Lucian, whom she had found out was polyamorous, if it would be fine if she dated. He agreed, but after Karen found that the relationship could not continue like this, as well as budding feelings of loneliness because of her distance from Lucian, she broke off his relationship with him and began a new one with Shion.

Known Pokemon
Karen is known to have at least 14 Pokemon:

Appearance
Karen's appearance is something that she is quite proud of. Although not slender to the degree of some models, she is still thin and curvy, with semi-wide hips and a bust that she flaunts constantly when she wishes to. She generally wears revealing clothing, such as her favorite outfit; a yellow double-spaghetti-strap tank top that cuts off at her midriff, one set of straps loose and hanging on her arms, and white hiphuggers that do her curves justice. Her silver hair is also something she is proud of - she grooms it daily and has been growing it for years.

During her time with the Mask of Ice, she wore an extremely low-cut black evening gown as her outfit for most of her tenure.

Personality/Psychology
Karen is upbeat - she will never back down from a fight (she is usually the one that instigates the fight) and never quit, no matter how tired she may be. In battle, she is fierce, wearing the opponent down with the trickery of the Dark-type, then moving in for the kill.

Outside of battle, Karen is incredibly flirtatious and seems to have no shame. She will flirt with anyone, and generally enjoys getting silly reactions from those she speaks to. When she is serious about flirting with someone however, her tone becomes far more seductive. Karen used to be a heavy drinker, but after a spat with Agatha, she became more responsible with what happened to her. Friendship and trust are strong traits for Karen, and she will never forgive someone who has betrayed her trust or her friendship. She will even speak casually to her friends, even though those friends are on the opposite side (for example, she spoke normally to Janine during her time in Team Rocket). Karen is also wary of most people, and has stated that she trusts few.

During her time with the Mask of Ice, she became childish, a reflection of her true nature - she had not developed as well she could have after her first run with him. Afterwards, she retained most her her personality, but has become less confrontational.

Karen is naturally a bisexual, having had relationships with both men and women.

Lance
Lance is Karen's boss as Champion, and the two have a high mutual respect. Karen has regarded Lance as one of the few people whom she trusts wholeheartedly. She also had a brief crush on Lance. Karen says that the two are nearly-evenly matched when it comes to battle skills, and she often teases him about his OCD and his lack of social and romantic skills.

Cynthia
Karen met Cynthia at a conference in Sinnoh, and was instantly swept off her feet by the Sinnohsian Champion's prodigious battle skill. She regards Cynthia as her one true love, and can barely string together a sentence in her presence. Cynthia remained ignorant to Karen's adoration of her for a while, regarding Karen as only a good friend, until Karen confessed to her when she thought she was dying. Cynthia responded by calling her a wonderful woman, but as she was neither bi nor gay, she could not return her feelings. Karen understood and has since attempted to move on. She kidnapped Cynthia shortly after rejoining the Mask, but returned her because of the danger it posed to her plans. After attacking Karin, Karen accepted the truth - she was never in love with Cynthia, simply transfixed by her; she hero-worshiped her. After the death of the Mask, she attempted to reconcile with Cynthia - they may not be friends, but they speak normally.

Agatha
Being the mentor of Karen during her early days of the Elite Four, Agatha constantly nags and corrects her, once even forcing Karen to act like a person she wasn't. Karen has yet to defeat Agatha in battle, despite having a type-advantage. The two ofter fight, but Agatha cares about Karen's well-being because of her similar past. When Agatha became unwell at the hands of her own self-torture to escape Team Rocket, Karen heavily questioned her own ability to defeat the Rockets.

Morty
Karen and Morty had little-to-no interaction before Team Rocket took him and brainwashed him; Karen was extremely concerned for his well-being, so she decided to rescue him. She treated him better than any other POW, and then took him to her old house, where Karen's Aunt Katie doted on him. Karen has developed passionate feelings for him, feelings he might return as he consented to having sex with her. Karen, however, viewed it as rape and started trying to push herself away to prevent more damage. She finally gave up on him after the final battle between the Resistance and Team Rocket, choosing to let him decide for himself what he wanted.

Jenny
Jenny began to show interest in Karen shortly after the end of the Rocket Insurgency, when Karen commented that she was bisexual. The two dated briefly, but after seeing that their lack of time spent together because of Jenny's work was putting a strain on their relationship, Jenny broke up with Karen.

Jasmine
Jasmine is one of Karen's best friends. Karen has shown a deep caring for her, jumping to her aid often and defending her when she is down. When Desukaan nearly killed her with her own possessed Steelix, Karen began her mission to stop the rogue Pokemon.

Karin
Karen Karin Williams is an alternate version of Karen from a different timeline. Karen met her and the two grew close almost immediately, regarding each other as sisters. They share many traits (although Karin suppresses some of them) as well as many differences.

Lucian
Lucian and Karen began dating after Karen asked him out. She had fallen in love with him, but the distance and their occupations took strain on their relationship, so Karen ended it.

Shion
Karen began dating Shion around the time Ashley Amaya was hospitalized. She initially flirted with the recently-outed lesbian, but was just teasing before realizing it was more than that. Karen began a relationship with her at the same time as her relationship with Lucian, but because his polyamorous lifestyle was so different and unflattering to Karen, she chose to continue her relationship with Shion. Karen has helped Shion come out of her shell more.

Trivia

 * Karen is portrayed by Cena on PokeTwitter.
 * Each of her Pokemon are named after dark, sinister, evil, or anti-heroic characters from fiction;
 * Millicent, Bellatrix, and Severus are named after Millicent Bulstode, Bellatrix Lestrange, and Severus Snape from the Harry Potter series of novels by J.K. Rowling.
 * Raphael is named for Raphael Sorel from the Soul series.
 * Alice is named for the eponymous character from Alice in Wonderland, specifically the 2010 Tim Burton film.
 * Bianca is named for Bianca di Angelo, daughter of Hades, from the Percy Jackson series.
 * Felicia is named for Felicia Hardy, alias the Black Cat, occasional partner of Spider-Man.
 * Victoria is named for both the Victorian era, where Gothic style was largely used, and for Vicky, the evil babysitter from The Fairly OddParents.
 * Emerson is named for Ralph Waldo Emerson.
 * Penn is named for illusionist Penn Jillette.