This is mostly a character analysis of Dean Winchester using Pokemon. I spent way too long trying to pick out the right mons for how I view Dean and his character over the whole show.
This is less "pokemon I think Dean would pick" and more "Pokemon I feel represent Dean" and then reasons for him to have them. I'm 1000% ignoring region and what's catchable in Unova (the America based region). I'm going purely off of pokedex entries, species lore, and vibes. This is somewhere between fanfic, world building, and character analysis. It kind of gets all mixed together.
For this world I'm going with the idea of two groups of people fighting each other over some sort of god pokemon- those would be equal to heaven and hell. Michael is the leader of the heaven-allegory team and Lucifer is the leader of the hell one. Chuck is still their father- but he's fucked off to drink with Arceus, or something like that. An absent father. Angels like Gabriel or Cas deflecting would be them leaving the group- Changing their pokemon teams to distance themselves. There'll be more on the Heaven/Hell teams when I do Cas' list of pokemon and my nonsense there.
To start with, Mary was accidentally killed in some sort of attack/battle between the two groups. John, being John, decided to become a bounty hunter/cop of some sort and travel around with his boys trying to get revenge. Dean ended up falling into that life, but Sam wanted something different (He probably wanted to be a professor or something. Does Pokemon have lawyers? Who knows), and got out. He gets dragged back in by Dean and they go off and join a third group that's formed to keep the peace (the Hunters. Possibly led by Bobby or Ellen or someone like that. John was not part of the group because he does not believe in working with others). It eventually ends up under Sam's leadership.
I'm sticking with a team of six to make things consistent if I decide to do other characters/people want other characters. Six is also my favorite number, so it works out well. My own personal challenge is to not give someone my favorite pokemon just because it's my favorite (Raichu). I'm trying to write them in the order he got them/got their base form. For Dean, I put the species and then their name. Because he very much names his pokemon. Then my rambling reasoning for my choices, followed by how I think he got the pokemon.
I feel like Dean never properly catches any of his pokemon. He just accidentally gathers them up and they adopt him like he adopts them. I think a bit part of his character is how easily he gets close to others- how easily he seems to make friends and allies. There are some characters he has pretty deep relationships with that are only in like, four episodes. And I forget that because the relationship always feels deeper than just a handful of time spent together (Claire, Kirssy, Garth, Benny, etc etc.) A lot of his character is about the connections he manages to make.
One Pokemon you're not gonna see on this list is Cubone.
Like, I get it. It's the dead mom pokemon. It's a shoe-in for both Winchester's team, it's their whole reason for getting into hunting in the show- the dead mom and obsessive dad.
With that being said, I don't think Dean's dead mom is one of the most important parts of his characterization. It's very important to his backstory and how he was raised- but that doesn't necessarily make it a big part of his characterization. Backstory and identity/characterization are tied together, but different people are going to put different emphasis on their history, and, to me, Dean's mostly got the idea of helping people from how he was raised.
Cubone is all about revenge and sorrow for it's missing mother, but it never feels like that's how Dean gets about it. He hunts because he was raised in it and he wants to help people. His motivation never really feels like it's all about hunting down Mary's killer. That's John's motivation more than anything. Hunting down Jess' killer becomes Sam's motivation in season 1. But it never really feels like Dean's. Dean wants acceptance, love, and to help people. Even as far back as Season 1. He wants to find his missing dad, he wants to help people as he does that. He wants his dad to be proud of him. He wants a relationship with Sam. He wants Sam to be proud of him. None of that really feels like a revenge-driven motivation.
The few times Dean wants to get back at someone- actually hurt them, it's mostly during the mark of Cain arc. Even when he wants to find Bela, it's never really a single-minded search for her. In Changing Channels he mentions he's wanted to kill "the Trickster" since the mystery spot- but once again it's not the single minded focus that Sam gets when thinking about revenge. I just don't think cubone fits Dean's character when you look closely at it. It might end up on Sam's list- but I just don't think it belongs on Dean's.
So with that being said, enjoy.
Special Case: Revavroom (Baby)
There's a car pokemon. Yeah, it's gotta be there. I was going to put Baby onto Dean's proper team- but Baby was John's to start with. And while she's associated with Dean she's also Sam's car/home. She felt too special to just be a pokemon on Dean's team. As much as people joke about her being a Winchester…is it really a joke? So to compromise, she's John's old pokemon that he left with Dean (and Sam).
Sam and Dean take care of and travel with their dad's old Revavroom. She doesn't really belong to either brother- her pokeball was lost with John's death. She was John's only pokemon- he'd used to keep several but after Mary's death he abandoned all but the Revavroom. He would have gotten rid of her too, but she was a pokemon he got with Mary-one that she loved dearly- he couldn't make himself abandon her too.
She traveled with the Winchesters for their whole lives, carrying the boys when they were small, keeping guard over them when not with John. After John's death Sam and Dean told her she was welcome to leave (even if it would tear them apart), as she didn't belong to them and her pokeball was gone, but she loved the boys and stayed with them.
Dean is her main caretaker, and he's very protective of her- getting angry if Sam dares to try to put any kind of dumbass contest costume on her. "Baby is a lady. Get that shit off her". And Baby- enjoying that Dean gave her a name and love- agrees with a vroom vroom. If anything happens to Dean, she gets upset and tries her hardest to comfort Sam. Baby feels very maternal towards Sam and Dean, thinking of them as her children in a way. If Sam and Dean separate, she tends to stay with Dean over Sam. If Dean is away, she protects Sam as best she can (but does get annoyed about the weird costumes he tires to put her in).
Dean's Team of Six:
Appletun (Crumble)
Appletun was the second pokemon I thought of when choosing a team for Dean. I knew I had to give him at least one food based pokemon. Mostly because of how Dean constantly shows affection and love through giving or cooking food. We have flashback scenes of him feeding Sam as a child, making sure he got what he wanted. We see him in Season 8 and beyond being happy with the Bunker having a kitchen. Baking Jack a cake, making Sam his weird egg white omelet with chives on it, and his pride in making a good burger. Food is important to Dean's character, both in a 'he likes food' way and a 'food is affection and connection way'. Yes, he likes to eat, and food is a comfort to him. But it's also connection and affection.
As for why Appletun and not a different food-based pokemon, I chose it for two and a half reasons. One of them is that Dean loves pie. He'd choose a pie pokemon in a heartbeat. Appletun, canonically, can be eaten (Pokemon Shield: "Children used to eat it as a snack"), and sometimes Dean needs a sweet treat from his pokemon buddy. Dean "Don't forget the pie" Winchester would have a pie pokemon. My half reason is that, honestly, Appletun is a little goofy. He keeps his little eyes lowered like ears and wears an apple hat. And Dean, deep down, is also goofy. He likes puns and bad jokes! He has so much fun LARPing, he quotes movies. He likes cowboy movies! He can list facts about his favorite cowboys! He craves being a goofball (more than he sometimes is allowed). Appletun Is just a big goofy pie baby. He goes well with Dean being a big goofy pie baby (when allowed).
My other, real, reason for the Applin line is that in-game it's about connection. In Galar there's a whole thing about giving them as a gift to romantic partners and it helping the pair stay together. You have a side quest where you get two lovers Applins so they can trade them. While in game it's romantic- the idea of this food pokemon being a connection is so very Dean. So for a character that uses food to show connection, I wanted a pokemon that was all about connections.
My lore is that as a kid, Dean only heard that Applins were meant to be given to the most special person in your life, and that would keep you together always. Being young-around 8- Dean didn't realize quite what that meant- but Sam had been asking for a Pokemon for months and this would be perfect. Little Sammy was his most special person- his baby brother, plus Sam thought dragons were cool! That meant Applin was perfect! And he'd seen some in the forest outside town. So out Dean snuck-out to find an Applin for his brother. He had no pokeballs, no money, but a fucking dream. It took him hours of hitting trees, trying to tackle the dragons himself, and a lot of tears before he ended up just asking an Applin half-hidden in the grass if he'd be his brother's friend. Dean had walked out of the forest with a weird green Applin to give to Sam. He was so happy to have a friend to give his brother, he didn't notice the red applin that was following after him, clearly enamored by Dean's stubbornness in trying to fight a dragon with his own 8-year-old hands.
Sam, being overjoyed with his new shiny friend, went to go acquire a pokeball to officially catch the Applin (spoiler for if I ever do a Sam list). While doing that the shop worker noticed the other one following Dean and offered him a pokeball too (honestly, Sam didn't even need to use the puppy eyes, most pokemarts will just give kids a pokeball if they need one). Sam insisted on catching the one following Dean, that way he could give one to Dean like Dean gave him one. The applin agreed and allowed it to happen.
Later, after John came home, Dean defended the Applins to John- who wasn't very fond of pokemon anymore and didn't really want his kids to have them. But with both Dean and Sam having one, John felt he couldn't really take them away. Dean was a little embarrassed when he later learned that exchanging Applins was meant to be romantic- but he just declared that for them it was for brothers. For family.
Even when Sam had left to go to school (Or wherever he goes off to in Pokeworld), he'd still look at the Applin and think of Sam and their connection. When both of them broke the rules and stood up to John for something that was just for them. Something to remember the love between them. It evolved into Appletun during the years that Sam was off at where ever he is in Pokemon world.
Dean didn't actually mean to evolve his Applin. Dean was on his own for the first time- after Sam left John had followed after. He could finally start doing things that he wanted- 22 and finally able to be himself a little more. No John to judge him, no Sam to be a good role model for. He ended up slowly starting to spoil his pokemon- they deserved nice things and to be out of their Pokeballs more often (John hated it when the boys let the pokemon out. He hated seeing them). He was grabbing food for himself at a stall and his applin kept bumping into an apple on a display. Dean just shrugged and got it for her. Maybe she wanted a new apple to chill in? It turns out she was just trying to tell him she wanted to evolve- with the sweet apple so she could herself and what she was meant to be. He was glad that she was happy and could be herself (and a little glad about what it meant for him)
When he met back up with Sam both Dean's Appletun (Crumble) and Sam's Flapple (Pandowdy) refused to be separated for a good few hours, happy to be back together again. Both brothers pretended to be embarrassed about their pokemon, but really they'd missed each other like crazy. Even when the brothers fight, the apple siblings stay close together in solidarity. They don't want to be separated again.
(Years and years later he'd spend a few days finding another green Applin- it's gotta be fricken' special- to press into Cas' hands, mumbling something about 'part of the family' and 'shuudup and take it' with a blush on his cheeks.)
Sylveon (Bullet/Spitfire/Sweetheart)
Sylveon was another pokemon that I felt really strongly represents Dean. When I was making my list I went though and opened the ones I felt strongly about before going thought the dex and adding others that might work. Sylveon was one of the first pokemon I opened, I felt so strongly about it.
It might not be the first thing that comes to mind- mainly due to it's looks, but it just fits him. Sylveon was introduced in Gen VI when they added both fairy types and affection. To become Sylveon, an Eevee has to know a fairy move and have two levels of affection/love. That's the big reason I think it fits Dean. He's filled with love- an insane amount of love. He loves his brother, he loves his friends, he loves his dad even if John's done some fucked up shit, he loves almost all of the children he finds during cases, he loves Jody and Donna, he loves Ben and Claire like his own kids (He loves Jack, even if they had a rough start), he loved Benny (in whatever way you choose) who was a vampire he should have just used for help and then abandoned.
Like, insert Cas' entire confession speech here (and yes, Dean loved Cas, I didn't say it in the previous paragraph but like, do I have to?) Everything Dean did in the show was for love. He had enough love to break an angel's programming and help him break free of heaven. His love for his brother was enough to break Lucifer's hold on Sam to stop the end of the world. This man was created with so much love that it broke God's plan. If you cut him open, he would bleed love and pain (also blood). Him existing taught Cas to love, he broke an angel with the amount of love that's just radiating off of him. Like??
I feel that he'd love his pokemon the same. An intense amount of loyalty and love. Once he got one pokemon to truly take care of and love, he could not be stopped. The dam of love had broken and it was time to share it with any pokemon that he could bond with. At first he tried to pick pokemon that would be big and tough- that way they could help with John's revenge plot. Ones that would make John proud of him. But any time he tried to catch something it just didn't feel right. Actually using his Applin to fight felt odd, like it wasn't really meant to be. At least, not just random battles. He understood fighting to protect his brother, or to protect things smaller than him, but fighting for fighting's sake just wasn't him (at least not yet. Not that it would really ever be, but he wasn't into pretending it was just yet).
While walking back from an unsuccessful hunt for a pokemon John would approve of, he came across what looked like the tiniest Eevee he'd ever seen trying to attack Sandshrew. It wasn't doing very well- but the little thing was trying it's hardest. Before he could really think, Dean threw out Applin and attacked the ground type. The sandshrew ran off and he approached the eevee, who was now looking at the applin with suspicion. Dean sat next to the two pokemon and used his eight--years-of- wisdom and experience being a big brother to lecture the eevee about having to be smart if she was so small. That she needed to be careful and clever if she was going to go after people bigger then her. He told the little eevee that if she couldn't be smarter, then she needed a big brother to protect her while she learned- just like him and Sammy. He was clearly unaware that he'd just sold the eevee on becoming his new friend. So when he got up to leave he was shocked when she followed him.
He insisted that he wasn't good for her- his father would hate her and how small and weak she was. He stopped several times on the way home to tell her. He told her this when she jumped on his shoulder. He said it again when she nipped at his ear in annoyance. He told her again that she'd want someone else when she kept nuzzling where she bit his ear. He ended up returning to the temporary home with applin in her ball and an eevee on his shoulder,nipping at his ear and insisting on being caught. John was disappointed- to say the least. A runt eevee wasn't what he pictured his son having. Dean wanted to make his dad proud, but this little eevee was something else. Spunky and ready to take on the world. He'd already connected to it, so he accepted his new pokemon and declared she'd one day be an Umbreon- dark and dangerous. Perfect for what his dad wanted. He gave her the name Bullet, something that got a nod of approval from John, and offered her a pokeball.
However, no matter how close Bullet and Dean were- she never did evolve. She'd stayed an eevee for years. It wasn't until after Dean felt abandoned by both Sam and John that he decided that it was probably his fault. It couldn't be his little spitfire of an eevee's fault- she was perfect. Fierce, brave, and still tiny. There must have been something broken in him that- when he'd said that she rolled her little eyes at him and nipped at his ear. It took him a bit longer to really accept and understand what she'd been saying.
It'd started with her not responding to Bullet anymore- not that Dean had used it very often. It might have been her government name, but she was more used to Spitfire (around everyone) or Sweetheart (When it was just Dean and his team). He never understood why she'd never become umbreon (or even espeon); she'd turned up her nose at the fire/water/electric stones he'd offered her. No matter what area they were in, she'd stubbornly refuse to evolve. Dean dreaded the idea that she might be Sylveon.
Sylveon was…very pink and soft looking. His father would kill him before having a heart attack about it if Dean showed up with Sylveon. So Spitfire stayed eevee for years and years. Only evolving after Dean finally fully accepted that love wasn't a weakness and was something good. When he finally accepted that he did deserve love, and it wasn't wrong to feel love. That the love he felt was a strength- one of his defining traits. It wasn't something to be embarrassed of- the love he felt was meant to be celebrated. Spitfire is a little dramatic and probably evolved during Dean's wedding or a big "i love you" confession. Much like Dean, she was better at showing love than saying it.
If anyone said anything about Dean having a pink fairy pokemon, well, Sweetheart had sharp teeth, a biting problem, and flesh ribbons.
Braviary (Feathers)
Braviary was the second to last pokemon I chose for Dean, there were a few different options for this one. I had stronger feelings about the other four, but the fifth and sixth spots I wasn't as sure about. I had a few horses (both as a ride and because cowboys), a few bears, an octopus (it's a gun and because…Dean and his hentai), and even a squirrel. I picked Rufflet/Braviary due to it's dex entries. They're all about standing up for and protecting friends. Having scars is a badge of honor for them, and they stand up no matter how big or dangerous an opponent is. It's also known to have anger/aggression problems- which is something else that does fit Dean at times.
The other reason I chose braviary is because after having two smaller pokemon, Dean does need something that would make his dad a bit more proud of him- something other than his little apple dragon and tiny eevee. A big tough bird of prey is a good 'manly man' pokemon but it's personality still fits Dean well. Acting big and tough on the outside while just wanting to protect people on the inside (and being actually dangerous). Someone willing to do anything for his friends/family. It fits his early season characterization: trying hard to be John but also a lot softer underneath the bravado. Trying to hide and pack away the softness to be the person John wants him to be.
Dean met his rufflet the summer when he was 11. Him and Sam had been parked at Bobby's pokemon ranch for the summer while John went off to look into something. Bobby hadn't had a problem with the applins or eevee, unlike John. But Dean still knew he had to find something tougher. Then maybe he could help out his dad with protecting others (that's what his dad did, right?). Dean had been helping out around the ranch when he spotted the braviary that had nested in a tree right outside the fence of Bobby's land. Dean was fascinated. Braviary was big and noble and perfect; just what he was looking for. He was smart enough now to know that picking a fight with the bird was a bad idea, so instead he did something he'd never done before. Went to the books to research. He'd figure out how to earn the bird pokemon's respect. Then it would join his team, and his dad would be happy with him. It was the perfect plan.
He looked though all of Bobby's books, ignoring the man when he said he could help Dean out. Dean wanted to figure this out himself- that way he earned the respect of the bird pokemon on his own. He read and he read and he read, looking for any and all information on how to charm the valiant pokemon. It was a lot about being strong, brave, and proud of both. Dean could do that. He had a ton of scars from his attempts at keeping Sam safe. That'd be impressive to the braviary. So he went to work.
He stood at the edge of the property- just inside the thin wire fence, and showed off his scars. He described them to the bird pokemon- going into every detail about how he got them, and how much it hurt, but how he worked through the pain. The braviary was unimpressed by him. So Dean tried harder. He came back the next day and told the bird about good he was about the pain, and how he was brave and strong. The bird remained unimpressed.
Each day Dean came back- for a week- trying to charm the braviary into being his new team member. Talking about how tough he was- how strong and brave he could be. But the bird remained unimpressed. Nothing he could say would get the bird to do more than raise an eyebrow at him. Dean refused to give up, however. Even if he didn't end up catching the braviary, he wanted to get it's respect. It was the principle of the thing. So out he sat- getting into staring contests with it, trying to out stubborn the bird.
While he did, he started talking about why he had scars and bruises- trying to keep his brother safe. Trying to keep his two little friends safe and healthy. The bird seemed more interested in this, so Dean went on. He spoke about wanting to keep people safe- to help those he cared about. How he wanted a big and strong partner so he didn't have to force his two buddies to grow up too fast (he knew how that was and it sucked). Somewhere along the way he lost sight of his goal to get the bird to join him- he just wanted to get out his feelings and how heavy it sometimes felt. How he wished that his dad was home more often so he could stop having to grow up as fast as he was.
When he finished speaking, the braviary nodded at him from the tree he was perched in, accepting and understanding. The two sat quietly for the rest of that day. (It would be years before Dean discovered that Bobby had been aware of what he was doing and had heard that entire conversation.) The next day, Dean- still refusing to give up- sat down by the fence and was surprised when the braviary flew down towards him, holding an egg in his claws.
The bird pokemon pushed the egg towards Dean, letting the boy take it. The wild braviary didn't want to be on a team, but did trust this kid who had the weight of the world with it's own egg. Dean promised to look after the rufflet that would hatch. That he wouldn't make it grow up quick like he was forced to.
And with that, Dean spent the next few days with the egg. Taking it on walks, keeping it warm, and talking to it. Telling the egg how Dean didn't actually care how tough the bird was- he just wanted his new friend to be happy and safe.
The egg hatched after a week and the rufflet that popped out was a lot like Dean himself. He loved showing off, acting tough, and trying his best to protect everyone. Even if he was too small to really do much.
Feathers, as Dean would call the rufflet, grew into a strong pokemon. Evolving when Dean is about fifteen. It remains one of his most aggressive Pokemon- but in moments of calm Feathers likes to curl up with the smaller pokemon under his wings- keeping them safe and close.
Arcanine (Husian?)
Other than Cubone, Arcanine is the other pokemon that most people assign to Dean when making teams. And this one I agree with. Dean is very dog-coded. He's loyal to a fault, loving, and trusting. The amount of trust he puts into people is astounding- actually. Season six with trusting Cas comes to mind as a major moment. If someone earns Dean's loyalty they have it forever.
Arcanine is really unique in pokemon in that it mentions China in a few of it's pokedex entries. There's not many pokemon that mention real world locations in the dex entries, but this also gives us more to work with. Seeing as how it talks about China we can guess that it's based off of the Chinese Guardian Lion statues (石獅; shíshī). Which are meant to be protectors. Normally they're in pairs- with the male having a ball and the female having a cub. They're yin and yang- protecting the house and the family. They sit outside temples and keep away spirts and other things that might want to harm it.
But Arcanine is only one pokemon- so I like to think he represents both the lions. Arcanine is described as both beautiful and powerful. Many are captivated by it's regal majesty and anyone that hears it's bark is left in awe. It blends the ideas of both yin and yang together.
They've also got elements from the Xiezhi (獬豸), which eat corrupt people and can tell right from wrong. (They resemble the Japanese version, the kaichi a bit more (as it's described as a horned lion, rather than a goat) but the dex mentions China, so the xiezhi.
Dean's a protector- he keeps his and his own safe. We get that shown to us in episode one. That's one of the reasons that Arcanine fits his character. But also, Growlithe is a good fit for Dean as well. I like when both the starting and ending evolutions fit. Growlithe's dex entries feel like they were written about Dean. "It has a brave and trustworthy nature", "It protects it's territory", "Extremely Loyal. It will protect it's trainer from harm".
As for why I went Hisuian, I just really liked the pokedex description of it. It talks about how it's big and bulky- but still graceful in battle. It can trick it's opponents into dodging the wrong way because of how it moves. I also just like the rock typing for Dean. It's strong and sturdy- just like him.
As for how he got this one, she was a gift from Bobby. I am feral for found family and father figures who think they'd be awful but they're the best dad a Dean could ask for. Introducing Bobby at the end of season one was peak and the best decision the show made. I would shoot a hundred John Winchesters just to get one Bobby Singer. This man looked at these two kids and went 'well, I guess I gotta do my best and parent them' even though he thought he'd be shit at it. I love Bobby so much and I'm gonna stop now before I turn this into a Bobby Pokemon mini-list.
Dean gets his Growlithe the same summer he gets his rufflet egg. Bobby heard Dean venting to the bird pokemon (he mostly wanted to make sure Dean wasn't going to get attacked) and wanted to do something. Dean had already had a rough life and he was only 11. And it wasn't gonna get any easier with John Winchester taking care of him. He couldn't just steal Sam and Dean- but he could give Dean something to help.
Bobby looked over the dog pokemon he had- he needed sheep dogs on the ranch- and tried to figure out the best for Dean. The boy needed something that'd be big enough to help him keep others safe- but also a friend. That's when he decided on one of the the Hisuian Growlithes he'd just gotten. They weren't trained just yet- so they'd be easy to hand off to another trainer- and they'd be loyal and protective. Just like Dean.
He claimed that she just 'wasn't working out' and handed her off to Dean, who took it very seriously. He was trying to think of a name when Sam insisted that 'Pepper" would be a good name for her. Dean gave in, mostly because Sam didn't get a pokemon- so he could help name the one Dean got. Even then, he almost never used the name. Normally refering to her as Darlin' or Miracle.
She was, much like Dean, stubborn and willing to take on things way bigger than her. She didn't like listening to Dean until an incident where Dean jumped in front of something to save her. Then she was loyal to a fault (much like him).
She evolves into Arcanine when Dean's about fifteen- just after rufflet evolves into Braviary. The two pokemon have a bit of a rivalry going.
Dragapult
Dragapult was the first pokemon that came to mind for Dean when I started thinking about this little project of mine. I knew that Dean needed a caretaker/parent pokemon on his team. That's such a big part of his character. That he takes care of his brother as a child, and how that's been his life goal ever since he was four. Sam's first steps were to him, he went hungry for Sam, he gave up everything to protect Sam, he sent himself to hell for Sam. He's a caretaker (I will fight the world about my mama Dean headcanons. Let this man be the mom he's always wanted to be. He deserves to be called mama). He needed a pokemon that is about being a caretaker.
The list of caretaker pokemon isn't super long- pokecenter pokemon (Chansey, Audino, and Indeedee) are used as nurse pokemon. Then we have the most famous mom pokemon, Kangaskhan. None of the Pokecenter pokemon felt right. Chansey and Audino are more about healing and gaining experience in game, while Indeedee is more of a servant pokemon. Kangaskhan is the og mom pokemon- it carries it's baby with it and worries about how the kid will grow up.
But that's also all the dex entries really said- it worried about the child, and wanted to protect it. Not all children- or even all other pokemon. Just it's child. And that felt too limiting. And then we have Dragapult and it's line. While it came to mind first, I did put it aside to look at others, because Dragapult is one of my favorites and I"m biased. I wanted to make sure it was the best for Dean and not just my favorite.
Dreepy are known to be weak and need protection- They're so weak a child could beat one. They find the fastest Dragapult and basically attach themselves. And the Dragapult love and worry about their dreepy. All three pokemon in the line talk about just grabbing Dreepy- or other pokemon if they can't find a dreepy- and taking care of them. They don't care about species- just that they have someone to care for. And not only that, but the dreepy want to be with them- they want to be loved and taken care of by Dragapult.
That felt very Dean. It's not just about keeping Sam safe. It's protecting anyone he views as family. That's expanded since he was a kid-and it's not just about his blood family. It's anyone. He collects people that he wants to keep safe and happy. For a more funny reason, Dragapult also throws Dreepy as an attack- and the pokedex says that Dreepy loves this. It's all very Dean. Was thrown at things to attack as a child, wants to keep other children safe, but understands that some of them are insane and want to hunt. He gives them the tools they need to be happy and as safe as possible. This honestly feels like the most Dean-Pokemon to me. Both the first stage and the final stage fit him well.
Like with all his pokemon, he didn't mean to get his dreepy. He was sent on a 'solo mission' from his dad when he was 18- his first one. He was supposed to get rid of a bunch of ghost pokemon that were haunting a building. When Dean got there, he found that the ghosts weren't actually trying to hurt anyone. They were just playing tricks- ones that weren't great for the people living there- but they weren't malicious. He could battle them- but he figured a better way would be to find them somewhere else to go- that way they didn't come back to the building when he left (he wasn't going to kill them. They were just trying to be themselves. There was nothing wrong with that).
So he asked around and found someone that owned a joke shop/mystery spot a few towns over- someone that was glad to take in all the ghost pokemon and let them pull all the pranks they wanted on him and the people who paid to get pranked. The ghosts were all pretty happy to go- other than one. There was a dreepy that did not want to leave her corner. Dean wasn't sure if she was scared or just attached to the place, but he didn't want to just leave her behind.
So he sat down and asked what she wanted- if she didn't wanna live at the joke shop, what did she want. He'd try to find a trainer for her, too. One that would be what she wanted. He wasn't sure exactly what happened- but Dreepy then flew into his hair and rested there happily. Ready to go with Dean and be his new buddy. (It didn't occur to him that all she wanted was kindness and affection). He ended up calling her Shrimp as a joke- but the name stuck. She refused to answer to anything else for the rest of her Shrimp-y life.
She evolves into Drakloak when Dean's 24, as Dreepy doesn't evolve until level 50. When Dean's 27 she evolves for the second time into Dragapult.
Tinkaton (Charlie "Pink").
So when I make pokemon lists for characters I always pick a bunch and then narrow it down. On my big lists I normally have some silly/meme pokemon that I put on as a joke and then eventually take off for my more serious choices (as serious as giving Dean Winchester Pokemon can be). Tinkaton started as me being silly; "Hehe, Dean is a girl dad to chaos gremlins", but then I actually thought more about it and the more it made sense.
Dean has relationships with fascinating women- specifically platonic/familial relationships. The women he ends up romantically involved are really cool, pretty, and normal. But his female friends/adopted family? They are all completely insane and chaotic. Sam has these women in his life too, but Dean always seems to have a stronger connection to most of them. It's probably because Dean becomes a bit more of the main character in later seasons so he tends to get a little more focus.
Charlie was a normal ass person who went 'actually, I am going to become a hunter and then go on a lesbian uhaul trip with Dorothy after knowing her for six hours'. Someone described Claire "I don't need a degree to be a hunter" Novak as "Angry blonde agent" and Dean knew right away who it was. Krissy (who should have gotten more than two episodes) threw herself into a hunting group and stayed there because she enjoyed it, even if she had a way out. Even in early seasons we had him with Jo- trying to help a rebellious younger woman that he did care about.
Even Jody does some truly chaotic things. My brain goes to "I have invited Sam and Dean to dinner now let's talk about sex and birth control- boys why aren't you helping me?". I love Jody she's so great. Someone tries to get into Bobby's house and she tries to keep them outside because 'you probably have a body in the house'. Iconic. Donna (her wife, no one can tell me otherwise) vibes so well with Dean. "Hey do you know how to shoot a gun? No. Welp! Here you are!" What an icon. We even see it a bit with Mary, when she's young and a bit when she's back from the dead. Eileen might be Sam's girlfriend- but if we had more time she'd also have been Dean's new bestie. All the women he platonically loves are insane. He has a collection of (lesbian) chaos gremilns that he loves fiercely.
He's a magnet for somewhat chaotic and fun women- and that's what Tinkaton is. Tinkaton is a female only species that's known for causing problems on purpose. They hunt down metal pokemon to steal their body parts to make a hammer. Half the time they don't even need to- they're just doing it for the funsies. Tinkaton (which is 100% a pokemon on Claire's list, as well) is a representative of Dean's tendance to adopt/be adopted by chaotic women.
That's also how he ends up with Tinkaton on his team. One day Drakloak showed up with a tinkatink on her head in addition to the dreepy that normally hung out there. Dean was confused as to where the little pink creature came from- and why his pokemon just brought it to him. He'd have been cool just keeping her, but he figured he should make sure he knew where she came from first. That way if the tinkatink belonged to someone, they could get it back.
This lead him to meeting Charlie- She was trying to take down a company that was run by a man named Dick Roman- one that was profiting off of abusing Pokemon. The tinkatink was a pokemon that Charlie had rescued- but then it got stolen by a random drakloak. When Dean brought it back- they decided to work together to take down Roman enterprises. Neither of them really liked the idea of what was happening continuing.
While working together they clicked- their senses of humor, their mutual dweeb-ness, their love of pokemon- it all fit together well. During the adventure, the tinkatink decided she liked Dean and Drakloak better- so she wanted to stay with him. He named her after Charlie- because much like the redhead, this pokemon was dropped on him and just fit.
He normally calls her "Pink" or "Pinkie" to go with calling Charlie "red". He gets Pink when he's 25, with it evolving at a normal level. It evolves into Tinkatuff right before he goes to find Sam (This time bringing Charlie along with him- that's his little sister now and she needs to meet their brother). She evolves for the second time when Dean's 28- right around the time that he meets Cas.
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This is Dean's main team of six. There are probably other pokemon he uses- but these are the ones that he'd consider his partners.
This is mostly just me going off about Dean's character by using pokemon. Join me later when I hopefully do a list for Cas and Sam (and maybe write an actual fic about this world)
