been meaning to write out my thoughts abt grimsley for a while now.
Disclaimer that I'm getting basically all my info from what has been documented on bulbapedia, since I've only recently gotten back into pkmn again and missed years worth of pmex events and whatnot. Take everything I'm writing here with a grain of salt, and I'm more than happy to be corrected if I cite something in here that's just blatantly wrong. With that said. Evidence that I think about this guy far too much.
Backstory and personality
Grimsley's backstory is as intriguing as it is vague LMAO. The description provided from bulbapedia is:
He is the son of a distinguished family that fell into ruin. As a result, he developed a gambling addiction.
No indication of how or why his family was distinguished (Were they wealthy? Were they successful or famous or otherwise socially influential? Were they of a distinguished bloodline? We'll never know), nor what caused it to fall into ruin or when. Incredibly open-ended, which for a guy who likes to write is both freeing and incredibly daunting.
What we DO know from this is that Grimsley likely grew up in a wealthy family. This is corroborated by these lines from his Sync Pair Story in pmex:
"My past isn't all sunshine and daisies, kid. Back when I lived at the family estate, I had to learn how to read people..."
"Adults can be tricky, see. I was in a situation where I had to suss out who was being straight with me and who was trying to use me."
"Eventually, I discovered how to do that. It's all about goals and intentions—figuring out what people want the most."
"That's what drives people to do what they do. Figure that out, and you'll see through any lie or bluff... That, kid, is how you win a game."
...
"It isn't difficult, by the way... I simply memorized the sound of your footsteps—nothing more."
He addresses the darker side of being part of an influential family; that he was surrounded by adults that wanted to lie to him and use him, presumably for his position in society, and he had to learn to read their intentions for his own self-preservation. Yikes.
This ends up being a pretty significant influence in his character, though. We can assume from this kind of upbringing that he's likely not only learned to read others, but also to avoid being read by others. He even says this in one of his lines in pmex:
"Lots of things make me happy, but I don't let my emotions show."
Oh yippee a guy who hides his real feelings behind a smug-ass smile!! We've all seen this guy before!!! FUCK!!!
We also know from that initial character description that the fall of his family's reputation was a direct cause of his gambling addiction. And I do appreciate the specificity of "addiction" used here too. It's not a casual thing for him; presumably, it's detrimental. It's not too hard to draw the connection here, that perhaps his family's fall from grace drained their wealth and Grimsley first turned to gambling as a last-ditch effort to win some quick cash to keep supporting the lifestyle he'd grown up with, only for it to develop into an addiction that continued to drain his earnings.
The gambling addiction lends itself to a couple of other traits that Grimsley repeatedly demonstrates in pmex in particular; that he's night owl and that he's a thrill seeker. Between this and the Mantine Surfing in Ultra Sun/Moon, he really paints himself as an adrenaline junkie. He says this in numerous ways in pmex LOL, here's just a couple of examples:
"I'm not really a morning person... I tend to stay up late battling most nights."
"Some people say nights are calm and relaxing, but for a thrill-seeker like me, they get the blood pumping."
Attitude towards luck and victory
I was admittedly a little confused at first when I was reading through Grimsley's quotes, because despite being a gambler, he really doesn't put a lot of stock into luck. But that confusion only lasted about a second because yeah, of COURSE a gambler would know just how fickle Lady Luck is, and know that more often than not, you need to actually work to tip the scales in your favour.
"You've got me wrong. All-or-nothing games aren't my style."
"It's more important to master the cards you're holding than to complain about the ones your opponents were dealt."
"If you're a true Pokémon battler, you'll reflect upon your loss and think about how to win next time!"
He's incredibly matter-of-fact in the face of loss, repeating sentiments that one needs to learn from their mistakes in order to perform better next time. That sort of tenacity is certainly admirable in regards to Pokémon battling, but I can't help but wonder if that attitude carries into his gambling habits as well... This idea that results are all that matter, and continuing to strive towards victory regardless of any other factors.
"Whether or not you get to fight at full strength, whether or not luck smiles on you--none of that matters. Only results matter. And a loss is a loss."
"A good contender just seeks the next victory without bragging after winning, and without getting upset after losing."
"But this loss will make me shine even brighter next time... If I think that way, it's not too bad."
*I will note that some of his lines in B/W are a bit contradictory and makes it a bit difficult to discern his potential attitude towards deception. He repeats ad nauseum that results are all that matter -- a beautiful loss is still a loss, and an ugly win is still a win -- which makes it sound like "victory at any cost" would be a sentiment he would align with, but he never outright says anything to condone cheating or deception, and also emphasizes the importance of reflection and learning from past mistakes, which seems like a graceful and honourable way to accept defeat. In pmex, I think his appreciation for honesty is a bit more prevalent. I think it might be fair to assume that his experience being lied to by people with ulterior motives in his youth dissuades him from repeating the same behaviour.
I guess all of this is assuming we can take everything he says at face value LOL.
Yes there's a whole section for this, hear me out. There's something so stupidly endearing about how this guy refers to himself like an old man LOL. He refers to himself as "ol' Grimsley" and "uncle Grimsley" in both Sun/Moon and pmex, a somewhat depreciatory way to refer to himself while also establishing himself as some sort of older mentor figure to the player character.
There's a couple moments where he seems to purposefully concede victory to the player character. In the pmex main story, he's caught lying about the result of a coin flip to try to boost your confidence. Less reliably, in Sun/Moon when he similarly asks you to guess the result of a coin flip, there is literally no way you can lose, which I mean. That's probably just the devs pushing the plot forward (can you imagine? No Sharpedo for you.), but it's fun to think that perhaps Grimsley also rigged that one and just wasn't caught LOL.
In Sun/Moon when he teaches you to ride Sharpedo, he indicates that he's taken it upon himself to teach others the skills he's learned, once again emphasizing that he sees himself as a mentor figure:
"That's right... The role I'm meant to play now is to teach others what it means to ride..."
His appearance as a smarmy-looking businessman and his reputation as a gambler actually end up being a bit contradictory to his personality, where he scolds the player character for attempting to lie, praises traits of honesty and earnestness, and generally seems kind and willing to help the player. Once again, it wouldn't surprise me if his treatment of the player character is a deliberate 180 from how he was treated by the adults around him in his own past.
The title of "uncle" is actually a pretty apt one for someone like him; a trusted older figure to provide guidance but still maintains a degree of distance. All the fun without the responsibility. It suits him a lot in my opinion.
I'm leaving this for last because it's the most speculative. There's one line in Ultra Sun/Moon that has stuck with me since I first read it:
"Sometimes you have to lay everything on the line in life, and risk it all... When I did that, though, I'm afraid I lost. I took to walking along the shore in my despair. And before I even noticed what I was doing, I ended up riding Alola's waves together with Sharpedo and Mantine...
There's something in this paragraph that just... gives me such a depressing vibe. I think it's the stakes he's presented -- laying everything on the line and risking it all -- and the use of the word "despair." That's a really strong word to describe a really empty, helpless feeling, and that word paired with the mental visual of him walking along the water... well it certainly paints a depressing picture.
I do wonder if we're meant to get the idea of him having suicidal ideation from these lines, because that's certainly where my mind went. For all of his graceful acceptance of loss that I mentioned earlier, we have to assume that his gambling addiction is slowly digging him a hole that's only getting harder and harder to get out of. Despite his appearances, despite his status of one of the Elite Four, he's got to be suffering from such an unsustainable life style. I wonder if his retirement from the Elite Four and his move to Alola was for the purpose of rehabilitation.
Whatever the reason, clearly it's been working for him, indicated by that last line in the paragraph above. That he went from walking the shores in despair to riding the waves; maybe still chasing those thrill-seeking impulses, while allowing himself to heal from the loss that almost took everything from him.
