Oleana Pokemon Guide

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Oleana is one of the most interesting characters in the entirety of Pokemon Shield and Sword, even more so than Chairman Rose. Her unwavering loyalty and her sense of compassion make Oleana a conflicted character, yet in the end, she remains loyal to the Chairman.

Even after his arrest, Oleana does volunteer work in his name to assuage her guilt, atone for her actions, and try to improve Rose’s reputation again, even while he’s in jail. She makes many appearances through the game, the animes, and the mangas, though she is mainly seen at Rose’s side.

At a Glance

Oleana can be found in the Pokemon Sword and Shield games, in the Pokemon short animated release on Youtube – Pokemon: Twilight Wings, briefly in the main Pokemon anime series, in the Trading Card Game, and in two mangas – Pokemon Adventures and Pokemon Journeys: The Series.

She is the tallest woman in the entirety of Pokemon, standing at 5’11”, and is highly intelligent with a usually calm and collected demeanor. However, when the main characters try to get in her way, Oleana is known to lose her temper. She grew up and lived in extreme poverty until Rose offered her a job. Oleana remains eternally loyal to him for giving her a chance and, by way of employment, providing a better life for her.

She has five Pokemon, though all five are only ever seen in the games and in Pokemon Adventures. In her ranks, Oleana has Frosslass, Milotic, Salazzle, Tsareena, and Garbodor.

Garbodor was her first Pokemon and, in Pokemon: Twilight Wings, was shown to be with her from the very beginning. In the Sword and Shield games, the best way to fight her Pokemon is to have a strong Fire and Ground-type team. Though if you’re concerned about her Milotic, having an Electric or Grass-type Pokemon will greatly benefit you.

Who Is Oleana?

Image from Wiki Fandom

In the Pokemon games, Oleana can only be found in Pokemon: Sword and Shield. In these games, Oleana works as the vice chairman and right-hand of chairman Rose, the head of the Galar Pokemon League, and the Chairman of Macro Cosmos.

Oleana is demonstrated to be a highly responsible and intelligent woman. She’s normally calm and collected, though she can become enraged and adopt an almost psychotic expression when people try to get in the way of her job. She has a fierce loyalty to Chairman Rose and often does whatever it takes, even manipulating others into doing her dirty work, to help Chairman Rose achieve his goal.


As with most of the other character’s in Pokemon: Sword and Shield, Oleana’s name is based on a plant. She is named after a type of olive, Olea, and a poisonous garden flower called oleander. This helps to define her relationship with two Pokemon in her team – Salazzle, and Garbodor.

In her Pokemon Wiki entry, Oleana’s only noted friend is Chairman Rose. Oleana serves as both Chairman Rose’s secretary and the vice chairman of Macro Cosmos. Oleana is unwaveringly loyal to Chairman Rose because he gave her the job that allows her to rise out of the extreme poverty she lived in for most of her life.


Image from Bulbapedia

Oleana is depicted as tall and very slender, with pale skin, green eyes, and long blond hair that splits off into wavy sections near the bottom. In Sword and Shield, Oleana wears a long white penguin-tail coat with the sleeves rolled up, a flared-out red shirt, a black pencil skirt, sheer black stockings, and matching black platform heels.

In terms of accessories, Oleana keeps it somewhat simple with a black choker, black hoop earrings, and a silver bracelet. She also wears some red lipstick and keeps her fingernail’s painted red. Oleana has no other outfits in Sword and Shield. She stands at 5’11”, making her one of the tallest women in the entire world of Pokemon.

Sword and Shield

In Pokemon: Sword and Shield, you can face off against a number of champions and enemies. Oleana ends up being one of the people you have to face off with and beat in order to progress the story. To fight Oleana, you need to progress far enough into the story that you find her in Wyndon.

There she is attempting to prevent anyone from reaching Chairman Rose while he is having a conversation with Leon. When you enter Rose Tower, Oleana will threaten to beat you to pieces and then proceed to challenge you to a battle.

Her Pokemon

Oleana has a pretty varied team, which can make preparing for her fight a bit difficult. In her team, Oleana has Frosslass, Milotic, Salazzle, Tsareena, and Garbodor.


Image from Wiki Fandom

Frosslass is a level 50 Ice and Ghost-type Pokemon. It is weak against Rock, Steel, Fire, Ghost, and Dark.


Image from Wiki Fandom

Milotic is a level 51 Water-type Pokemon. Milotic is only weak against Grass and Electric.


Image from Wiki Fandom

Salazzle is a level 50 Poison and Fire-type Pokemon. It is very weak against Ground (four times the damage) and weak against Psychic, Rock, and Water.


Image from Wiki Fandom

Tsareena is a level 50 Grass-type Pokemon. It is weak to Poison, Flying, Bugs, Fire, and Ice.


Image from Wiki Fandom

Garbodor is a level 52 Poison-type Pokemon. It is only weak against Ground and Psychic. At the first chance, she gets Oleana will Dynamax her Garbodor.


Oleana’s fight isn’t terribly difficult, so there is little you need to do to prepare for it. However, if you’re concerned, make sure that you have a strong Ground and Fire type team.

Two of her Pokemon are weak to Ground-type moves, and two are weak to Fire-type moves. Utilizing the move Earthquake with a Pokemon like Mudsdale or Excadrill will be incredibly helpful in having her fight end sooner rather than later.


Oleana Battle

Milotic is likely the most annoying Pokemon to face off against due to its recover move. However, if you Dynamax an Electric or Grass-type Pokemon against Milotic, you should be able to bypass that and recover fairly quickly.

When it comes to Garbodor, as mentioned earlier, Oleana will Dynamax them as soon as possible. In order to counteract this, having a Pokemon on your team, like Excadrill, is a huge benefit. Considering that Excadrill is a Steel-type Pokemon, the Poison-type moves that a Dynamaxed Garbodor utilizes will be rendered null.

After the Battle

After defeating Oleana, when her Pokemon began to run wild and Dynamax on their own, Oleana pleads with you, the player, and Hop to stop rose from unleashing Eternatus, and thus the Darkest Day legend. She does so out of fear that releasing Eternatus will end up harming Chairman Rose.

Oleana can be found after you complete the story of Pokemon: Sword and Shield. After Rose is arrested, Oleana starts to participate in some voluntary services on Rose’s behalf. She discloses Rose’s past of previously working in a coal mine and ends up giving you one of her prized League Cards. Despite feeling bad and wanting to atone for what Rose has done, Oleana is still incredibly loyal to him.

After completing the story entirely, Oleana can be found in the Old Cemetary at night, looking for Rose after having heard rumors of him being seen in the Crown Tundra. When Peony appears, Oleana confuses him for Rose. Learning that Peony is not Rose, Oleana becomes angered but quickly clams down before leaving via a Flying Taxi service.

Finding Oleana in the Old Cemetary

Oleana at the Old Cemetary

It can be a bit of an ordeal to find Oleana in the Old Cemetary after the story ends. To start, you need to fly to the Slippery Slope Max Lair. Once inside, you need to speak to Peonia. Keep talking to her until she eventually asks if you’ve heard a rumor about a long-haired woman who visits a grave every night. Once you have this clue, grab your bike and travel to the Old Cemetary.

Once you arrive at the Old Cemetary, weave through the headstones until you find Oleana standing beneath a tree. Once interacting with her, the cutscene will start.

Pokemon Anime

Oleana can be found in two different animated Pokemon series – both the main one and a youtube short series called Pokemon: Twilight Wings.

Main Series

Oleana in the Anime
Image from Wiki Fandom

In the main series of the anime, Oleana debuted in Sword and Shield, Slumbering Weald!. In this episode, Oleana visited the Galar Energy Plant with Chairman Rose just in time for a burst of Galar Particles to escape from the reactor core. Regardless of the escaping Galar Particles, Oleana pushed for more energy to be injected into the reactor core.

Unknown to Oleana, this decision eventually prompted Eternatus to awaken. Meanwhile, Oleana has one of her employees follow Goh and Sonia, both of whom are trying to learn more about the Darkest Days legend, foreshadowing the awakening of Eternatus.

In a later episode, called Sword and Shield: From Here to Eternatus, Oleana makes another appearance as she stops Goh from reaching Rose. However, in Sword and Shield: The Legends Awaken!, she loses the battle that unfolded in the Hammerlocke Stadium foyer, and the protagonists can continue pushing on to try and stop Rose and Eternatus.

Afterward, Oleana returns to Rose’s side, joining him in a helicopter to watch Eternatus transform into Eternamax and take on Ash, Goh, and Leon. Following the defeat and capture of Eternatus, Oleana goes into hiding with Rose.

Pokemon: Twilight Wings

Oleana, Twilight Wings
Image from Bulbapedia

Pokemon: Twilight Wings is a short animated series released on Youtube. It was inspired by Pokemon Sword and Shield and featured eight seven-minute episodes. In this series, Oleana makes several appearances, giving viewers more insight into her character than the main series did. This series also serves as somewhat of a prequel for the Pokemon: Sword and Shield titles.

In Pokemon: Twilight Wings, Oleana first debuts in Letter, the first episode of the series. In this episode, Oleana accompanies rose to a children’s hospital. In Training, the second episode of the series, Bea calls Oleana to tell her that she will be training at the Wild Area and thus will be away from her Gym. Oleana then informs Rose of this.

In the fourth episode, Early-Evening Waves, Oleana was with Chairman Rose when he approached Nessa. Later, Nessa visits Oleana and asks her to tell Rose that she would be successful as a Gym Leader and a model.

Young Oleana, Twilight Wings
Image from Bulbapedia

In Assistant, the fifth episode of the series, Oleana is the central focus. In this episode, Oleana is leading Macro Cosmos while Chairman Rose is away for the day. Eventually, she reunites with him in the evening.

During this episode, her past as a laboratory assistant is explored, and we learn that her least elegant Pokemon, Garbodor, has been with her since the beginning of her career, long before she was Chairman Rose’s secretary and vice chairman. We also learn that Oleana leads somewhat of a lonely life and is married to her work, even if she is not, particularly in love with what she does.

In the seventh episode, Sky, Oleana informs Chairman Rose that Leon has not arrived at the stadium yet. Later, she is seen on the field with Chairman Rose, waiting for the match. In the final episode, The Gathering of Stars, Oleana is seen doing volunteer work at Galar Mine.

The only Pokemon that Oleana is seen within both series are Milotic, Garbodor, and Tsareena. Although all of her Pokemon are carefully curated to be elegant, and from an all-female species, Garbodor is the exception, depicted as having been with her from when she was a Research Assistant to when she finally was hired by Chairman Rose.

Pokemon Manga

Oleana can be found in two different Pokemon Mangas, Pokemon Adventures and Pokemon Journeys: The Series. Her appearance in Pokemon Journeys: The Series, however, is brief.

Pokemon Adventures

Oleana in Pokemon Adventures
Image from Bulbapedia

In Pokemon Adventures, Oleana only makes an appearance in the Sword and Shield chapters of the manga. However, unlike the anime and Pokemon Journeys: The series, several of Oleana’s Pokemon are seen and demonstrated to fight, even if none of their moves are known to the reader.

Oleana makes her debut appearance in Crackle!! Practice Battle. Here she makes her first appearance at Rose Tower. In this chapter, Chairman Rose receives a call from Leon, who wants to endorse, and wants Chairman Rose to help endorse, Henry Sword and Casey Shield for the Gym Challenge. Her role in this chapter is minimal and more of a background role at best.

Throughout the entirety of the Sword and Shield arc of Pokemon Adventures, Oleana is constantly by Rose’s side, doing as he asks or going out of her way to keep certain tasks off of Rose’s plate – mainly commanding subordinates.

She fights the Gym Leaders in an attempt to keep them from confronting Rose when they learn of Rose’s plan to bring harm to Galar. However, she is unable to stop several characters from sneaking inside the building. In the end, however, Oleana only wants to keep Rose safe, even if that means forsaking his dream.

All five of her Pokemon are seen in the series, though none of their moves are ever told to the audience. Tsareena was the first to make its debut. Oleana used Tsareena to attack Raihan after he snuck into the Energy Plant. Later Tsareena was utilized to stall the Gym Leaders who were attempting to climb into Rose Tower.

Frosslass is the second Pokemon to make its debut. She was utilized to attack Raihan and was later used to stall the Gym Leaders, the same as Tsareena. Salazzle was the third to make a debut and was only utilized, unsurprisingly, to stall the protagonist, Gym Leaders.

Milotic was the fourth and was only utilized in, shockingly, to stall the Gym Leaders.

Garbodor was the last to make its debut. Garbodor was used to stall the Gym Leaders, and in its Gigantamax form, it fought Bea’s Gigantamax Machamp. As one can expect, as per the usual path of the Pokemon storyline, Oleana lost this fight and could no longer stall the Gym Leaders.

Until it comes to defending Rose, Oleana plays more of a background role. This helps to showcase how she does play more of an assistant role when it comes to Chairman Rose acting like a showstopper, yet has a hidden talent.

To be able to stand up against all of the Gym Leaders is something that only top Pokemon fighters ever get to do. Even if Oleana only made it so far and ultimately ended up failing, it does go to show just how much talent she has and how hard she works. Both she and her Pokemon are very strong and you certainly wouldn’t want to face her unprepared.

Pokemon Journeys: The Series

In Pokemon Journeys: The Series, Oleana makes an appearance in JNM13 and JNM14, performing the same role that she does in the anime – that of Rose’s advisor and unwaveringly loyal supporter. Her Pokemon debuted in JNM14, though only Milotic was seen, and none of Milotic’s moves were demonstrated.

Trading Card Game

Trading Card Game Oleana
Image from Bulbapedia

Oleana makes her appearance in the Sword and Shield series of the Pokemon Trading Card game, specifically in the English series. Her cards’ first release, however, was in the Japanese Rebellion Crash and English Rebel Clash expansions.

In the Sword and Shield series of the Trading Card Game, her card allows for a player to move an opponent’s Trainer card to the bottom of their deck after discarding two cards. Oleana’s card artwork was done by Yusuke Ohmura. Her Full Art Card and her Secret card were released in the same expansions, drawn by kirisAki.


Question: Is there a difference between Gigantamaxing and Dynamaxing?

Answer: Although the difference may not mean much, there is a notable difference between the two terms. Both Gigantamax and Dynamax allow for a Pokemon to grow and become more powerful but unlike Dynmax, Gigantamaxing a Pokemon changes both its size and appearance. Gigantamax replaces the Dynamaxfunction within Pokemon: Sword and Shield.

Only certain Pokemon in the game can Gigantamax, which means that you may miss out on this feature entirely. The Pokemon who are able to Gigantamax may seem like a long list, but they comprise of only a fraction of the Pokemon in Sword and Shield. On that list are Snorlax, Charizard, Pikachu, Eevee, Corviknight, Lapras, Blastoise, and many, many others.

Question: Who invented the Dynamax band?

Answer: Oleana invented the Dynamax band, securing her position as Rose’s right hand and certifying her undeniable intelligence.

Question: What kind of Pokemon does Oleana use? 

Answer: Oleana’s team is varied, but it is interesting to note that she is the only villain in the entire series who does not utilize a Steel-type Pokemon. Instead, Oleana has an Ice and Ghost type, a Water type, a Poison and Fire type, a Grass type, and a Poison type.

Oleana Pokemon: Conclusion

Oleana is a complicated character who comes from a complex background. Although it is easy to see why she is loyal to Chairman Rose, it can prove difficult to understand how that loyalty often overcomes her moral qualms with his plans.

One could theorize that Chairman Rose often kept Oleana in the dark about his actual plans or the potential consequences of them, but then again, one could also theorize that Oleana had no moral qualms with his plans.

On the other hand, however, the guilt she clearly feels at the end of the game – enough to perform voluntary hard labor, demonstrates that she does maintain a strong sense of morals. That is, if you accept it’s her own guilt and not just a desire to make Rose appear better in the public eye.

Regardless of what you may believe about Oleana, she is certainly a complex figure who is so invested in her work that there is little else in her life. One can only hope that she finally gets better than what Chairman Rose can provide her. Regardless, as the Sword and Shield arcs of Pokemon come to a close on all fronts, I have little doubt that Oleana will ever see a life outside of her intensive investment in her job.

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