This section applies to the ILCOE.
May's Pokémon (current and former), here listed in the form in which they were first seen in the story, are Spirit the Ninetales, Quilava, Butterfree, Skarmory, Pikachu, Lapras, Larvitar, Trapinch, Mutark, Floatzel, Blaziken and Stantler.
Spirit, as a Vulpix, had an unusual dark coloration, as well as the mysterious ability to shift in and out of the physical world, making herself insubstantial and sometimes invisible. One day she was found by a young girl living in New Bark Town, May, who took her in and befriended her as a pet. They intended to go on a journey together, but after Spirit was kidnapped by a rich kid in town, May became paranoid about others desiring her as well, and therefore she did not take her with her on her journey. While waiting for her at home, however, one day Entei paid Spirit a visit, told her that she was 'Chosen', and by the power of his touch he evolved her into a Ninetales as well as creating a necklace with the symbol of the Chosen that she now carries.
Quilava was raised in capitivity by Professor Elm as a Cyndaquil and volunteered to be a starter. When May picked her, however, they never truly bonded, since May had always disliked Cyndaquil and avoided using her, and in turn Cyndaquil didn't like her much either. Eventually Taylor tricked May into trading her for his Charmander, but Taylor was never very interested in her even after this, preferring the clones that his brother gave him, and so never really used her, instead just keeping her in stasis inside her Pokéball.
Butterfree lived in Johto as a Caterpie and was caught by May early on her journey. Seeing as Caterpie aren't the brainiest Pokémon around, she does not remember much of her Caterpie days.
Skarmory was hatched in the cliffs near Alumine, in the largest Skarmory nesting grounds in the world. He was caught on his first flight from his nest, but did not mind capture.
Pikachu's mother was the wild Pikachu that Ash's Pikachu saved out of a river once during his adventures in Kanto. Much later, she was caught by a trainer who still later moved to Sinnoh and eventually released her near the Lake of Purity, where she decided to stay. Pikachu was not as young as Skarmory when he was caught and had been looking for a trainer when she found him.
Lapras lived at the Lake of Purity but never felt like she fit in and was crying when May caught her. Unlike the others, Lapras never wanted a trainer, but she put up with it anyway, too timid to protest.
Larvitar was raised in captivity for the Larvitar breeding program and released at the Lake of Purity shortly before May caught him. Little is known about his past, however, beyond that he was very young when he was caught.
Trapinch lived in Thunderclap Cave as one of the various Pokémon that relied on the Flashes of the Electric Pokémon in the cave to see. He always wanted a trainer, though he was rather young when he attacked May.
Mutark is a Mutark, and as such she is a bit unusual. She does not speak much, being that normally she is in an infantile form, and nothing is known of her past.
Floatzel has loved to battle since she was a Buizel and evolved when battling some Carvanha that bit off one of her tails, but it regrew during the evolution and she defeated them in revenge. She always wanted to find a trainer strong enough to take her to the League, and in May, her wish was granted.
Blaziken was caught as a Torchic as a replacement for Quilava, chosen specifically because he was enthusiastic about battling and excited to get better. Even before May caught him, he had been a fighter all his life, competing with the rest of his clutch for food and developing his various Fire attacks.
Stantler had a trainer many years ago, a boy, but was released after he committed suicide. Afterwards, she had a calf and migrated to the Ouen Safari, wishing to make a tentative return to being trained.
As I started writing this section, I wasn't sure how much I'd actually want to say about May's Pokémon, since most of them seemed to be pretty minor characters, but then I ended up typing out a whole bunch. I guess I'm just that rambly.
Spirit is the first that strikes me as noteworthy here, primarily because of all the characters in The Quest for the Legends, she may oddly enough be the closest to your typical Mary-Sue. She is chosen by a legendary, has a special coloration and special nickname, can use several special powers not typical of her species, wears a mystical pendant... Now, I wish I could tell you that this was all intentionally done as a subversion of Mary-Sue tropes, but no, unfortunately, I really have no idea what the hell I was thinking. You see, the idea of Spirit is really, really old - while Spirit the character never appeared until chapter 31 of the ILCOE, the idea had been around since the UMR if not earlier, and in fact she was scheduled to make her first appearance in chapter 37 there - but the last chapter I ever wrote of the UMR was chapter 36.
But even though I never actually wrote it in, her appearance had been meticulously planned by that point. Spirit was one of my many attempts to tie up multiple plot holes with an addition that seemed to have been foreshadowed all along: she was both the "something" that had been stolen from May's family a couple of years ago and a partial explanation for Gyarados's weirdness and why Suicune starved him. I don't remember precisely when (much less why) I decided that she would be unusually colored and have a special pendant, but apparently I did, and then I went and drew her all over and somehow, even by the time I wrote chapter 31 of the ILCOE and should really have known better, just cheerfully wrote her in with all these ridiculous qualities and an even more ridiculous backstory. So now I'm stuck with her, like most every other old idea in this fic.
That said, she is not all bad. I did deliberately make her rather vain about her own specialness, and I like how that came out generally. The whole Chosen plot is a subversion of the general Mary-Sue-with-special-necklace chosen one concept, as shown in chapter 51 where we discover that Entei was just using her and really doesn't care about her at all, and I love her denial about this and insistence on treating being a vessel for Entei's selfish longing to live on past the War as some sort of a great honor. And her interactions with Floatzel are absolute gold to write, with her throwing a hissy fit the moment Floatzel dares to point out that this whole Chosen thing is awfully vague and strange, which of course it always was.
And speaking of Floatzel, I love her. She was a completely spontaneous addition - I was writing chapter 43, thought, "Hey, they're on water and May needs a new Water Pokémon; she'd definitely try to catch one," and the moment I'd decided on Floatzel, she just became this amazingly fun character to write. The quirky speech pattern is somewhat out of nowhere, but I love that I finally gave May a Pokémon who actually matches her enthusiasm about battling and winning, and I can tell that I'm going to have a lot of fun with that in the future. And her interactions with everyone are really, really fun to write. I just have to hope everyone else likes her as much as I do.
Lapras's brief interactions with her replacement in chapter 43 were particularly interesting to write. Lapras' subplot in general is one of my favorite things I've decided to do in this fic; I really don't remember exactly why I did it, but I know it wasn't until the ILCOE. I think it might have occurred to me when writing chapter 32, when Lapras took a Thunder she wouldn't have needed to, and it struck me that out of all her Pokémon, Lapras had gotten the worst treatment from May, and she had been established, ever since the original, as having been extremely lonely and an outcast before May caught her, and not really satisfied with being caught. It seemed only natural, then, that she would eventually just get fed up and demand to be released, and that made for a lot of fun development for May and a lot of fun May/Alan and May/Lapras scenes, not to mention the aforementioned Lapras/Floatzel interactions in chapter 43, when Lapras realized that her leaving was not developing May in the right direction at all and other Pokémon would keep battling for her and being loyal to her. I'll miss Lapras, for these final chapters she was in; I really enjoyed what it did for the story and I think it made it substantially better.
Larvitar, however, may be the most significant of May's Pokémon. Mark was right in his spontaneous assessment in chapter 53: he was very, very young when he was caught, proportionally younger even than Mark's Eevee - and Larvitar grow up a lot slower than Eevee. After May caught him, he began to view her as an idolized mother figure of sorts, and as he was never forced to have much contact with May's other Pokémon and didn't seek it out himself, he failed to fully develop and use proper Pokémon speech and other social skills even as he evolved, all the way until May's battle for the Championship where he finally finds the motivation to speak. (Tellingly, his first words are of course quoting May on not being weak.) Having been brought up in May's harsh, competitive training regime, his sense of self-worth is tightly bound to how he does in battles and whether she is happy with him, resulting in his tragic idea that maybe he can make up for losing to Mewtwo² by killing Taylor, because that's what May's been saying all this time, and being pretty much just an overgrown child, he has yet to develop any sort of sense of when people say that sort of thing repeatedly and passionately while still not quite meaning it.
I don't know if it sounded like I was pulling this out of my ass in chapter 53, but I wasn't; I've been planning this for several years. Looking back, I feel like I should have set it up a whole lot more, but elements like (obviously) his lack of speech and his extremely tight attachment to May and desire to please her have been there all along, whether they were actually noticeable or not. Now, of course, it's kind of too late, what with him being released, but I definitely loved every moment of writing him, knowing what was to come. Poor guy. Ironically, just like his victim, he was messed up by a poor parental figure who obliviously ruined him while meaning well. Hopefully he'll find a better future than Taylor did.
Finally, there is Stantler. However random the capture seems, this has been in the works for ages; she's been Tyranitar's planned replacement pretty much ever since I decided on how he'd leave. Admittedly, initially I only knew her species and actually planned for May's Stantler to be male; it was only later, when I was thinking about the fact most of Mark and May's Pokémon are male, that I became attracted to the idea of making her female, and when her capture drew nearer her personality began to emerge in my mind. I'd always meant for Stantler's capture to be a significant moment for May as she chooses consciously to catch a weaker Pokémon to prove that she could be a 'nice' trainer, but slowly it became clear to me that Stantler would help her in a more direct way, being a far more mature character than, well, any of the other Pokémon and quite perceptive to May's awkward attempts at pretending to be nice.
I was writing their conversation in chapter 57 when May, realizing she should be trying to get to know her Pokémon instead of just battling with them, asked Stantler what her old trainer was like. (I'd known for a bit by then that Stantler had had a trainer before.) While showering, I thought about what the answer to this question would be; I ran through possibilities but none of them seemed to feel right, and after a bit of deliberation, I concluded he had been nice but there seemed to be something more to it than that, something I couldn't quite put my finger on. Then it suddenly dawned on me that he had killed himself, and that that was why Stantler was so extra-concerned about May: after losing one trainer, she took any sign that not everything was right with May very seriously. Suddenly everything made sense and I came out of the shower knowing that I had discovered The Truth About Stantler.
That is in all seriousness a very illustrative example of how a lot of my plotting and characterization happens: I don't know what's going on, and then, after thinking about it for ages, I suddenly figure out the missing piece of the puzzle that causes everything to make sense. It's a miracle how often it works out this perfectly.