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Villains:

Tesoro

“Such a shame that such a pretty face was wasted on such a scoundrel like you.”

Frankly, as long as HDC gets to keep their drilling rights and reasonable tax rates, Alex doesn’t care what the hell Tesoro does with Paldea. Of course, violate either of those things, and you’ll get the King William treatment, albeit less severe because Tesoro is hot.

However, since he ends up losing to Bibi, Alex may keep him as an associate, either to gain extra revenue from his pyramid scheme or as an assassin for when Alex can’t be bothered to capture someone himself. Again, however, if Tesoro ends up fucking him over somehow you can bet that Alex will be on his tail.

Unless he is in a situation where Tesoro could reasonably kill him, Alex wouldn’t hurt him too much so as to avoid permanently damaging his beautiful body. Instead, he’d probably strap him to a chair and make him watch as his fainted Gholdengo is melted down and made into gold bars.

Hemlock

“You should shave, you ugly bitch!”

Alex has a disdain for Macro Cosmos as it is the largest competitor to the Heriot empire. In my personal headcanon, they were also established recently, a bit before Monty’s oil business got its start from his lottery money. Its competitiveness comes from being much more aggressively expansive than the Devon Corporation and Silph Corporation. Now, where was I?

Even though they have a shared disdain for Alolans and their culture, as well as having a similar view on the use of Pokemon, Alex would likely offer clandestine support to Koa once he gets going, mostly through giving him supplies and blowing things up while Koa is out doing his thing. Once the tides begin to turn, Alex will smell the blood in the water, and ramp up the bombings to further destabilize the Alola division of Macro Cosmos, potentially even deploying his G-Max Pokemon. That being said, he’s also not a fan of Koa, and would probably turn on him once Hemlock is defeated, as he might pose a threat to HDC swooping in and creating a dependency on their oil.

Hemlock and Alex could potentially agree to split up Alola, but I don’t see that happening. Monty himself doesn’t approve of Alex’s actions, but he knows that he can’t stop him, so he just turns a blind eye and silently takes advantage of Alex going after Macro Cosmos. There might also be at least a bit of mutual respect between Alex and Hemlock due to their shared strength and greed.

Franco

“You’re so weak you can’t even take down a single wh*re and her shitmon?”

Again, Alex would try to offer support to Phos against Macro Cosmos through secret operations. Unlike Hemlock, however, there wouldn’t be any kind of mutual respect between Alex and Franco. Alex would frequently mock him for his height, unusual hair color, and his refusal to end Phos, as well as him not being as greedy as Hemlock and seeing Pokemon as something other than tools.

Alex despises megalomaniacs like Ghetsis and Lysander with “higher goals”, viewing them as delusional and fruitless. He would essentially treat Franco like a second-rate Colress, lacking both the logic and intellect that makes Colress formidable, instead focusing on a “common cause”. At least people like Hemlock are just in it to enrich themselves, which Alex actually holds in higher regard.

Morally Grey:

Silas

“Pathetic.”

It’s unlikely that they would ever meet unless Silas somehow ended up causing a massive issue for the Herriot conglomerate. That being said, the strength disparity between them is so great that Alex would probably take him as a joke. However, his weakness and lack of connections might leave him open to some torture, for both him and Wheaton. What’s he going to do, call the police? Alex would probably turn him in at some point, but only because keeping around a living voodoo doll would lead to some pretty bad repercussions if it ever escaped. Alternatively, Alex might just kill him, what’s one more dead criminal going to do to his conscience, even if he doesn’t deserve it? Nothing.
 
Tweny

“Insipid, blasted little f*cking bitch, who’s the loser now?”

Again, it’s unlikely that they would ever meet. Alex would probably just ignore him, but if Tweny pushed him and ended up activating Alex’s ASPD, Alex would crush and humiliate him as badly as possible. 

Emily

“You don’t deserve to save the world and you certainly don’t deserve to win any battles. You’re just a freak of nature, you just got lucky.”

Even though they have a shared hatred of Team Plasma and megalomaniacs as a whole, it’s unlikely that Alex would offer the goblin any form of respect. He would view her powers as cheap tricks and her bonding with her Pokemon as idiotic and unnecessary. He wouldn’t ever provoke her, though, but if for some reason she came after him, he’s probably just skip the battling altogether and just flat out unleash some ill-gotten military hardware on her.

Heroes:

Koa

“Have you ever tried dressing like a normal person?”

Alex would certainly appreciate any insight that Koa could provide him on Dragon types, however, he’d also likely discard most of it, as it would be tainted with Koa’s youthful naivete, especially when he realizes that Archaludon and Hydrapple are completely foreign to him. He’d also be somewhat annoyed by his tribal ties and emphasis on Pokemon bonding. 

He might offer support against Hemlock in some form, under the guise of moral convictions, however, Alex would certainly try to dispose of him afterwards. Alternatively, he could provide support to both sides in order to prolong the fighting so that they both bail out and then HDC can come in as a more “ethical” alternative, or simply just stay out and watch it all play out (and then of course, bring in the oil rigs). That being said, if Koa ever confronted Alex, he would make the battle against Hemlock look like a tea party. The only way Koa might be able to win is through an exceptionally well timed Z-Move, and even then Alex has crystals of his own as well.

Phos

“With a body like that, you should be out there doing f*cking Contests, not getting your ass kicked by me!”

Alex would try to offer her support against Franco, but he wouldn’t give as much as he does to Koa. This is because the urban environment makes it easier for him to get caught, and he also doesn’t want Phos to become a stronger trainer. He’d mostly just give her intel and let her do the work for him. Unlike Koa, however, there’s a bigger chance that Phos catches a whiff of Alex’s true motives. He’s probably leave her on her own after that, but again, if she goes after Heriot assets or reputation, he’ll absolutely drop the hammer on her. Due to her glove, he probably wouldn’t give her the pretty privilege treatment. He would try to avoid a physical confrontation, even though he’s physically stronger then her and better trained, he doesn’t want to catch the glove. Depending on the situation at hand, he’ll either approach with one of his stronger Pokemon already out, or just flat out skip battling altogether and reach for the gun. If conditions allow, he’d probably approach with some HSS/HPIS with him as well. That being said, he’d be glad to unleash his X-Transciever flamethrower in close combat. He would also probably mock her for having such a revealing outfit, especially if they were to fight; he loves to dehumanize his opponents. All that being said, he’s an entirely different beast from Franco, and I can’t truly predict how Phos would react to Alex helping her, or going after her. 

Bibi

“Your outfit looks stupid. Your glasses look stupid. Your shitmon [Ribombee] looks stupid. You look stupid. You are stupid.” 

This can go different ways depending on how they meet, but I generally think that they would not like each other. Bibi’s fluffy demeanor would definitely annoy Alex, probably not enough to trigger his ASPD, but he would definitely throw a lot of shade at her. I can also see her trying to be nice to his Pokemon in a non-battle setting, in the rare instance that they’re out, leading to Alex putting them back in the Pokeballs and yelling at her for spoiling them, and likewise she will begin to seethe about his treatment of his Pokemon.

As for how they would actually meet, I imagine Alex coming to the Blueberry Academy to deliver some kind of battling workshop, sponsored by HDC in order to gain publicity. He’d then battle Kieran in order to demonstrate how strong he is, and why Alex’s advice should be taken seriously. Once Kieran is crushed, that’s when the manipulation or buck breaking will start. This is what would really drive a conflict between Alex and Kieran. Whether he sets out on breaking him or manipulating him, if Bibi finds out, she won’t be happy. I’m not sure if she would try to physically confront him, as he is far stronger and larger than her, but she might try to call him out. 

Regarding Tesoro, again, it all depends on how and when they meet. Alex could align himself with Tesoro to enrich and empower himself, but if he got betrayed then he’d support Bibi out of pure spite. Even then, however, once Tesoro settles down into whatever scheme he sets up after his defeat, he might switch back just out of pure distaste for Bibi, especially if she challenges him afterwards regarding Kieran. 

Ayamu

“F*cking hippie!”

Once again, it’s unlikely that they’d ever meet, but if they did, they probably wouldn’t like each other. If Ayamu wronged Alex, he’d probably chase him down and force him into a fight, which he can probably win, but it can still go either way.

Axel

“Autist.”

Their cold and distant personalities would probably bounce off of each other, however, Axel may show interest in him if he knew that Alex had possession of both sets of Legendary Birds.

Alto

“Let me show you some real metal.”

It’s difficult to imagine them ever meeting, but Alex would probably just mock his outfit and music. Alternatively, Alex might be fake nice to him in order to get cheaper records out of him, but that’s unlikely given that Alto doesn’t listen to extreme metal.

Alto seems like a metallic hardcore, modern hard rock, nu-metal and “J-Metal” guy to me. Bands like Architects, Code Orange, Spiritbox, Jiluka, and Crush 40 come to mind, as well as stuff like Slipknot and Korn; “heavy” to the uninitiated but tame to true metalheads like Alex. Hell, even the extreme metal side of metalcore like Chimaira, Lamb of God, and Byzantine would probably be too much for him, in my opinion.

Azeile

“I caught Steel and Poison types just to deal with people like you.”

Not much is known about her, but he would view her Aura as “cheap tricks”, though probably not to the extent that he does with Emily, and would have a disdain for her team, as he hates Fairy types. Might bring Klinklang and Magnezone out of reserves just to spite her. If she does or says something that pisses him off, he might try to dehumanize her like with Phos.

Ruka

“[REDACTED]”

Again, he would probably just be annoyed by her. However, since she’s not pushy like Tweny, she would at best just get a snide remark from him.

Hairstylist

“What’s up with your accent?”

I forgot her name. Anyways, I have no idea how this would go down. He’d probably try to look her up and see if she’s good, and if she really wanted to give him a new hairstyle, he might let her do it. If she fucks up his hair, though, instant ASPD trigger. No restraints will be present.

Vega

“Nice hat.”

Well, they can’t actually meet, as Furia is basically a Legends game, but I imagine that Alex would probably try to gain magic and other secrets from her, either through purchase or manipulation. She would also get a bit of pretty privilege from him.

Rana

“Revolting.”

I don’t remember much about her besides the fact that she’s really annoying. So yeah, Alex would despise her. Might go as far as to hurt her and take her stuff if nobody is looking. Alternatively, he might try to get some magic or items out of her through purchase or manipulation, like with Vega.