Jessie's mother was a member of Team Rocket in order to pay for Jessie's education, so she left home when Jessie was 5, in order to search for Mew in the Andes under Madame Boss's commands (Team Rocket's then leader). She never came back. Jessie lost her mother and had to live in a foster home without money at all, where she usually had to eat snow to survive.
James grew up in a rich family. Sounds great, right? No. Being born in high-class society, he had to partake in activities he had little interest in, and his fiancee (who looks like Jessie, but acted far worse) was incredibly overbearing and tried to teach him to do things properly. The only friend he had in his childhood days was a loyal Growlithe who he left behind when he joined Team Rocket. Sometime during the Battle Frontier arc, his Chimecho became sick and he had to leave it with relatives, something that was clearly heartbreaking for him to do. He does get a Mime Jr. in exchange, though.
Meowth grew up as an alley cat and fell in love with a wealthy, but snooty female Meowth who rejected his feelings since he had nothing to give her. Meowth then tried to walk on his hind legs and talk like a human to make himself more unique. Unfortunately, this backfired since the rich Meowth then saw him as a freak.
Mewtwo from the first movie. When it was just a child-like Pokémon, Mewtwo had all of its childhood playmates die (clones of the first stages of the Kanto starters and Dr. Fuji's deceased child, Amber); as soon as it retaliates emotionally towards Dr. Fuji, Mewtwo's memories of them are wiped before it matured. When it awakens, Mewtwo learns (from Team Rocket) it is a clone of Mew created solely for experimental purposes, causing it to blow up the lab with everyone inside because of this. The Genetic Pokémon then gets taken in by Giovanni, the leader ofTeam Rocket, who sees Mewtwo as only a tool; upon finding this out, Mewtwo blows up the gym where it was being used in and returns to its island of birth, deciding to (rather understandably) Take Over the World. It's only after Ash's Heroic Sacrifice during Mew and Mewtwo's fight when the latter has a change of heart and decides to seek out and do better. It's a good thing Mewtwo learnt to move on, seeing as it later becomes altruistic and takes on other Pokémon to protect them, but in retrospective, Mewtwo is the original Woobie, Destroyer of Worlds of the entire series.
Ash's Charmander. It was abandoned by its overbearing jerkass trainer who lied to it about coming back to get it (when he had no intention of doing so). Charmander's loyalty would unfortunately be its own undoing as it waited in the pouring rain for its trainer to return, thus risking its life. Fortunately, Ash takes it under his wing.
Larvitar, from near the end of the Johto saga. "Address Unown" reveals the full story of how, as an egg, it was stolen by a greedy Pokemon poacher (using, from its perspective, a terrifying machine to take its egg), and it could only sense its mother being injured trying to save him. Expounded by all this being shown in Larvitar's mind to Ash and co., complete with sounding like a terrified little boy. When it hatches, Larvitar's so terrified of humans, it takes a courageous deed to get Ash to trust him, and a heartwrenching "I Know You're in There Somewhere" Fight to trust other humans, including Misty and Brock. Thank goodness Larvitar gets to earn its happy ending.
Chimchar might be the second in-line of Ash's Fire-type starters coming from an abusive former Trainer, after Charmander, but he might as well be the biggest woobie Pokémon of Ash's team. Before joining Ash, Paul adopted the Chimp Pokémon in hopes he could unlock Chimchar's true strength, yet he would be abusive to him, constantly belittling Chimchar for his failures. Even before Paul adopted him into his team and the Diamond and Pearl series started, the poor Chimp Pokémon had developed a fear of Zangoose after a traumatic experience where a pack of them chased him down; as he manages to knock them out in desperation, Paul sees this and deems it as worthy of adopting him. Chimchar's woobie status only grows in the Tag Battle mini-arc, where Paul's training regime for Chimchar is revealed to be his entire team attacking Chimchar in hopes he would reawaken his inner strength, which goes about as well as one would expectnote Chimchar is rushed to the Pokémon Center for medical help. Tired of not being able to unlock his true potential, Paul finally releases Chimchar into the wild, though Ash quickly recruits him into his team. The episode "Tears For Fears" also showcases a very emotional side of Chimchar, crying tears of joy when he's treated with kindness and love by Ash and co. after losing a sparing match, and finally overcoming his fear of Zangoose. Finally, the episode "Chim - Charred!" has him reawaken his true potential by activating Blaze after battling his former Trainer Paul, but goes berserk and attacks everything around — until Ash finally manages to calm him down despite suffering from several injuries. Since then, Chimchar finally grows stronger, and come his evolution to Infernape, he firmly evolves into an Iron Woobie — nevertheless, to say his past was dark and troubled is an understatement.
Even Team Rocketdeemed Paul's treatment of Chimchar as abusive. In the episode "Tears For Fears", Meowth, who was separated from Team Rocket earlier, finds Chimchar alone on a walk and, expressing he had no malicious intent towards him, tells Chimchar to move on from the past. Not to mention the trio happily cheer on him as an Infernape in the Lily of the Valley Conference. Even if Meowth has been sympathetic to other Pokémon numerous other times, how much of a woobie would you have to be in order for the entire trio of villains to cry out for you?
Ash's Tepig also follows the footsteps of Charmander and Chimchar. Tepig is usually positive, but episodes showed it becoming depressed whenever it lost. We later learn that its former Trainer abandoned it after losing, causing it to worry that it'll be abandoned again if it loses. Tepig also nearly starved to death, due to the rope its former Trainer used wrapping around its snout and preventing it from being able to eat. The kicker: Tepig is quick to try and befriend its former trainer when they meet again, believing that its Trainer had the best intentions for it. Tepig finally gets over its Trainer when he reveals that he didn't care for Tepig at all, and is still unrepentant over what he did.
Ash himself can be this in early seasons on the show. As a rookie trainer, people would always deride him for mistakes he made. He also had to deal with a jerkass rival who would always taunt him for how behind he was. Then, he has a disobedient Charizard that cost him a win in the Indigo League. Speaking of League, every time Ash tries to challenge one he'd get stopped in his tracks by another trainer, especially after persevering through some of his biggest rival throughout the regionsnote Gary and Harrison in Johto, Paul and Tobias in Sinnoh, Trip and Cameron in Unova, and Sawyer and Alain in Kalos, causing fans to both mock and lament Ash's inability to win a League. Thankfully, he wins not just the Alola League, but in Journeys he manages to beat three champions and crown himself as the strongest trainer in the Pokémon world, finally fulfilling his dream of being a master. About time, Ash Ketchum!
Ash also got his time in the woobie spotlight in the S1 episode "Pikachu's Goodbye" where he sees a teeming utopia of Pikachu and figures his Pikachu would be happier with the other Pikachu than with Ash. Turns out, it was quite the opposite. Pikachu was happy, but still missed Ash and when they got captured by Team Rocket. It's hard not to cry when Ash leaves Pikachu and a particularly sad song plays as Ash remembers all the fond memories he had of Pikachu. It's like losing a close pet. Though this isn't for long; if this were the season finale, this would have probably topped the tearjerkers list of the Pokemon anime.
Latias from Pokémon Heroes is a particularly heartbreaking example. She lost her mother shortly after she was born according to the backstory, and her father died shortly after leaving them with nothing but the Soul Dew, leaving her twin brother to grow up faster and raise his sister himself. Then, in an attempt to save Altomare and his sister, Latios gave his life to stop Oakley and the machine that drove her mad. So basically, Latias lost every single member of her family, and if we go by there being only one of each Legendary Pokemon in existence, lost all her species and relatives too. What's more is she's essentially a more childish human (though in a dragon-like Pokémon body) making this even more heartbreaking.
Mallow of the Sun and Moon series. Since throughout the series, it has her going through the Five Stages of Grief, it's hard to feel sorry for her for what she did with her deceased mother years prior.
Lillie of the Sun and Moon series is a shy Lovable Coward that fell victim to a conspiracy in her mother's company as a little girl. An incident with an Ultra Space portal left her traumatised and unable to touch Pokemon, with the scientist responsible covering his tracks and her mother too neglectful to really take notice (though she does end up regretting this). In present day she goes through many hoops to cure her phobia, and even afterwards she remains a bit of a Cosmic Plaything and an adorably timid little sister surrogate for Ash.
Manga
Emerald from Pokémon Adventures. His parents died and his relatives might as well be playing hot potato with him, each of them trying to dump him somewhere else. Because he's a midget, he couldn't do much of anything on his own and was picked on for it. As soon as some nice Pokemon try to help him out, said bullies mock him that he can't do anything without his 'tools'. He then resolves to do everything he can by himself, further alienating himself. If he had never seen Crystal and her selfless attitude, who knows what could've happened to him?
Also Blue and Silver for being kidnapped as children by a self-centered monster and only getting better because they escaped from him years later.
Cubone, as shown in the Video Game Woobies page. When a Cubone is born, the mother dies, and it then takes her skull and wears it (which is also creepy at the same time, but still). Cubone never shows its face to anyone, cries any time there's a moon at night, and the skull is stained with its tears. Depending on the region, it also has to contend with predators like Mandibuzz, who use the moment while it's most emotional to prey on it. Poor little guy.
The Porygon family could be considered a meta-example, once you realize that they will never appear in the anime again due to something that wasn't even its fault.
Banette doesn't even start off as a Pokémon. Instead, it starts off as a toy that gets played by a child, eventually abandoned and forgotten like it never existed. Then, instead of being able to rest in peace, a ghost possesses it and turns it into an animated doll filled with vengeance and seeks to get revenge on the kid that threw it away. Woobie, Destroyer of Worlds, if ever there was...
Absol, who is known as "The Disaster Pokémon" for the wrong reasons. It can predict disasters and tries to warn people that they're coming, but instead, the humans take it the wrong way and think that it brings disasters. Its Moon and Ultra Sun entries lampshade its misfortune.
Pokémon Diamond and Pearl: Volkner. Due to a lack of challengers to his Gym in Sunyshore City, Volkner leaves for the lighthouse out of depression. But once you talk to him, he'll go back to the Gym, and when you battle him and win, he'll be in high spirits again.
Audino is a cute-looking Normal-type Pokémon that only appears in shaking grass, but provides a metric buttload of Experience Points. This means pretty much every trainer will go Audino-hunting sometime or another just for the Experience Points. To make things worse, a high-level Audino sometimes heals your Pokémon while you're beating it up.
Though not quite on an N level, it's hard not to feel sorry for Bianca at times — heck, the game makes you break her yourself multiple times. She went on a Pokemon journey despite her father's opposition, but she couldn't become a strong trainer and defeat you or Cheren no matter how hard she tried.
This game has what may very well be one of the grand champions of this in the main series of games with AZ. Formerly the King of the Kalos region, he had a Pokemon he loved truly and dear to him in the form of a Floette. Yet it eventually died during a great war and was brought back to him in a coffin, sending him into pain-filled grief, determined to bring back his Pokemon. He built a machine that could and succeeded. But his grief turned to rage at the world that took his Floette away from him, turning his machine into a weapon that singlehandedly ended the war. Yet in all this, his Floette, appalled and saddened by his actions, left him. The resulting exposure of the machine's energy caused both to become immortal, and AZ walked the Earth for 3000 years to find her. He has a happy ending, in which he finally lets go of his anger and sadness, and meets her once again.His theme songreally drives his woobieness home.
Calem/Serena, the rival character to you. Considering the rivals in previous games, that might sound a bit strange. In this game, however, your rival is not evil or even an asshole. They don't need to learn any meaningful lessons about pride or power. They just want to be a good Trainer, and the only thing that's stopping them from that is YOU. You'll regularly beat them out of things that they really, really wanted, i.e the Mega Evolution ring, and you get to be the hero instead of them basically by virtue of getting there first. In other words, they're Woobies because they do everything right and it just isn't enough. You crush their dreams every step of the way. Serena's animation when you beat her makes it seem like she's about to burst into tears. As one person put it, you are their Gary Oak.
Pokémon Sword and Shield has the fossils: Dracozolt, Dracovish, Arctozolt, and Arctovish. Remember how dinosaur bones would be pieced together incorrectly in the old days, creating weird-looking Mix-and-Match Critters? What if those skeletons were actual living creatures? Each one looks awkward and silly at best, and at worst appears to be in constant pain; special mentions go to Arctozolt, which is always shivering as a result of its frozen body, and Arctovish, which has its head on upside-down and is stated to have trouble breathing in its Shield Pokédex entry. To rub salt in the wound, all four fossil halves are from different base creatures, so it simply isn't possible to have a Galar fossil that doesn't look like a horrific freak of nature. Is it any surprise that a lot of people feel really uncomfortable with using these Pokémon?
Legends Arceus has the Hisuian forms of the Zoroark line and Voltorb. The former is driven out of their homeland and gained the Ghost type from dying in the Hisuian cold and the latter is kicked around for their tendency to accidentally discharge their stored up electricity. No wonder modern Voltorb and Hisuian Electrode looks so angry!
In Pokémon Scarlet and Violet’s Teal Mask DLC, this can theoretically apply to two characters, who both share part of the story: Ogerpon is told of in legend as being an evil demon (“Ogre” in international versions) who terrorized the land of Kitakami and was stopped by the heroic actions of three Pokémon memorialized as “the Loyal Three”. However, the real story that the townsfolk refused to believe was that Ogerpon came to the region alongside a traveler, and both were seen as hideous and intimidating and shunned. When they donned special masks created by a sympathetic craftsman and returned, their anonymous selves were welcomed and even became popular among the people. However, three Pokémon became jealous of them, and in their jealousy, snuck into the pair’s cave outside of town and killed the traveler, Ogerpon’s only companion. Ogerpon attacked them in revenge, but the townsfolk only saw a murderous demon attacking three Pokémon seen as protecting the town. Now Ogerpon would never be able to go outside again, and the townsfolk even made a mockery of her story to the point where even the Ice Queen Carmine becomes sympathetic when she finds out the truth.
And then there’s Kieran. Despite being an average albeit eccentric kid, Kieran is constantly bullied by his older sister Carmine, and when he finally makes a friend with the player character, he’s still constantly losing in Pokémon battles against them, and then later finds out that the player and Carmine appeared to conspire against him to hide the truth about Ogerpon, despite him always wanting to meet the demon himself. After another battle, he gets so angry that he punches a memorial to the “Loyal” Three, which inexplicably revives them. Even though he was lied to, he still tries to help for Ogerpon’s sake and even finally convinces the entire town that the story of the demon was misinterpreted, but Ogerpon still barely gives him a passing glance. Losing control, he challenges the player to one last battle, with the victor keeping Ogerpon, and loses. After this, he retreats to his home and later back to his academy, obsessing about getting stronger and getting back at the player…we’ll have to see how that pans out in the second DLC, The Indigo Disk.
Given the circumstances, being that Kieran was borderline obsessed with the demon even before finding out she wasn’t evil, and was trying to forcibly take Ogerpon for himself when it was obvious she didn’t want that, it’s up to whoever plays the game to determine for themselves whether or not to truly sympathize enough to consider this a Woobie.
. It gets even worse in Galarian Form where the poor thing was possessed by a cursed slab while looking for someone that knew its face, losing its mask, the only thing it had left of its humanity, along the way.