In the Pokémon characters advance the plot in meaningful ways, while others simply serve as obstacles to be overcome by the player. In  Pokémon Sword & Shield, Oleana is a combination of both.

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Appearing several times throughout the main storyline, Oleana is Chairman Rose's secretary. Stoic, seemingly bored, and detached, Oleana remains distant for most of her interventions, providing some interesting insights but otherwise staying out of the action. However, her role in the story is much bigger than previously suggested, and she ends up being one of the most complex characters in recent memory.

Her Name Is Based On A Plant

A group of pink oleanders growing

Like in Pokémon Sun & MoonSword & Shield has some names that are clearly inspired on plants. Hop and Rose are obvious examples, and so is Oleana.

It is based on the oleander, a shrub or small tree cultivated worldwide in temperate and subtropical areas. Mainly ornamental and used in landscaping, the oleander is highly poisonous and can cause severe illness if consumed. Pretty fitting for a woman who's beautiful on the outside but more nefarious on the inside.

A Day In The Life

A solemn Oleana giving instructions in the Pokémon Twilight Wings anime

The "Assistant" episode of Pokémon: Twilight Wings centers around Oleana and reveals several things about her personality and backstory. Her determination and ion for Dynamax and Gigantamax quickly impress Rose, who eventually hires her as his assistant. She then works all the way up to Vice President of Macro Cosmos.

"Assistant" is an episode that provides some deep and complex insight into her life and behavior. She is married to her work but doesn't seem to enjoy it all that much and barely reacts to Chairman Rose's flattery. Oleana seems quite narrow-minded and aloof, but it's undeniable how intelligent she is. There's also a distinctive depressing tone to the episode, as Oleana's life is revealed to be quite lonely.

She's A er Card In The TCG

Oleana's er Card in the pokémon TCG

Introduced during the English Sword & Shield Series, Oleana is er Card in the TCG, released during the Rebel Clash expansion.

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The card can only be played after discarding two cards from the current hand. The opponent is then forced to reveal his hand. Furthermore, the player can choose a Trainer Card, should the opponent have one, and put it on the bottom of the opponent's deck.

She Shows Up In The Crown Tundra

The player interacting with Oleana at the Old Cemetery in the Crown Tundra DLC

Released in late 2020, The Crown Tundra DLC provides an entirely new area for the Galar region. Many new Pokémon become available, and regional versions of the Kanto Legendary Birds also debut. The DLC received generally positive reviews, with many considering it a logical continuation to Sword & Shield's narrative.

Oleana makes a small cameo once the player ends the Tundra's main storyline. She's at the Old Cemetery at night and states she's there after hearing rumors about possible Chairman Rose's sightings. Once she discovers it's actually Peony, Rose's brother, who's in the Tundra, she leaves.

She Is Macro Cosmos's Vice President

Oleana conducting a company meeting in the Pokémon: Twilight Wings anime

As previously mentioned, by the time of Sword & Shield's main narrative, Oleana is serving as Macro Cosmos's Vice President. However, and despite her seemingly important position, she's still seen as Rose's assistant, something she doesn't seem to resent.

Oleana indeed controls Rose's schedule and appointments. She companies almost everywhere and knows everything about his activities. The animes, both the main series and Twilight Wings, provide a lot more context about her true role in Macro Cosmos,  revealing she pretty much handles all of the company's day-to-day operations.

She Gets Her Own Punishment

the player interacting with Oleana while at Galar Mine in Pokémon Sword & Shield

The post-game for Sword & Shield reveals Oleana's ultimate fate. After Chairman Rose's plot gets foiled by the player, he apparently disappears and Oleana heads to the Galar Mine to do voluntary community service.

She's apparently regretful of her actions and wishes to atone for them. She remains loyal to Rose, though, and she even provides his rare League Card to the player when she's approached and interacted with.

She Has An Explosive Nature

Oleana enraged as she's about to battle the player in Pokémon Sword & Shield

Most characters in the Pokémon games aren't exactly expressive. Back in the DS days, animated sprites were the most these folks got. As graphics kept improving, so did the character's animations. Still, they remained mostly stuck with just one emotion. X & Y introduced the sunny group of rivals, and Sun & Moon gave fans the perpetually happy Hau.

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Never in Pokémon history has a character been as expressive as Oleana. While she spends most of her time in the games with a look of cool detachment, she eventually snaps when the time comes to battle her near the game's climax. Indeed, the anime reveals that Oleana is prompt to sudden bursts of anger.

She Invented The Dynamax Band

A Dyanamx battle between Dragonair and Giratina in Pokémon Sword & Shield.

Dynamax and Gigantamax are a huge deal in Galar. Nearly every gym uses the gimmick, turning Pokémon battles into real sporting events that include an excited and chanting audience. Galarians have Oleana to thank for this, as she's the inventor of the Dynamax Band.

A Key Item in the games, the Band allows Pokémon to Dynamax at certain Power Spots and perform Max Moves. And while players can only Dynamax once per battle, it's still visually stunning and adds an extra level of excitement to every battle.

Her Pokémon Team Has A Theme

Oleana and her Milotic in the Pokémon anime

Oleana has a team of five Pokémon. Three of them are level 50, one is 52, and her strongest is 52. She's battled near the game's climax and serves as the Macro Cosmos's last line of defense before the player challenges Chairman Rose.

Three of Oleana's Pokémon, Froslass, Salazzle, and Tsareena, come from all-female species. Furthermore, four of her mons are famous for their grace, with Milotic generally considered as the most beautiful Pokémon of all. All this suggests Oleana goes to great lengths to preserve her carefully constructed cool and elegant image, and this includes her Pokémon team.

She Has A Close Bond With Her Garbodor

Oleana as a lab assitant in the Pokémon: Twilight wings series

Oleana's ace is Garbodor, the Trash Heap Pokémon, a creature so foul that it literally feeds on garbage and waste. This is surprising at first, considering her four previous mons are all beautiful and graceful creatures. Once again, the Pokémon anime provides some explanation.

In "Assistant," Thrubbish, Garbodor's pre-evolution, is shown next to her while she's still a research assistant, long before Rose hires her. This suggests Thrubbish was actually her very first Pokémon and has been with her since the beginning. Furthermore, the fact that she chooses Garbodor as her final Pokémon, the one worthy of Dynamaxing, reflects the special place it has on her team.

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