Shitton of headcanon goes here

If you're going to play a character like Wes, or any Pokémon protagonist, for that matter, you're going to have to deal with one giant, glaring issue. Namely, their silent protagonist status. Wes, however, is different from other Pokémon PCs in that he actually has a background, and a few canon personality traits, sparse as they are.

(I'm just going to throw this short cutscene from the intro to Colosseum on here, because it give you a pretty good look at his character in just over a minute)

"Pokemon Colosseum: Opening Cutscene" (Watch on YouTube)

 

What we know about Wes canonically:
1. He is a former member of Team Snagem.
2. He was the best snagger in Team Snagem.
3. He betrayed Team Snagem and went rogue, destroying their large snag machine, and stealing the portable one in the process.
4. He blew the Team Snagem base to bits, crippling the group and alerting the authorities of its location.
5. He has a sweet-ass hoverbike.
6. He starts with two fully-evolved Pokémon, both of which are happiness-dependent.
7. He can seriously rock the slasher smile.

This is all information given to us right at the beginning of the game with his dynamic introduction. This is all we need to form a basic idea of who Wes is.

1. He's a thief, and a damn good one, at that.
2. He knows how to drive and maintain a motorcycle, and he knows his way around explosives.
3. He's got to be a damn good actor if no one in Snagem expected his betrayal. Or maybe they're all just idiots. Hard to tell.
4. He's not completely heartless, given that he had both Espeon and Umbreon, which must both be at maximum happiness to obtain.

None of that is headcanon, but rather what we can gather from in-game cues. This shapes a fairly solid character for the start of the game. After Rui is introduced as a secondary protagonist, however, Wes's characterization delves deeper into headcanon territory, as all of his actions are dictated by Rui's will. She's his 'morality leash,' so to speak, and I think that's why a lot of people don't like her. She ties the unarguably chaotic good character to a lawful good role.

Canon stuff out of the way, the following is officially headcanon territory.
( Great big long headcanon post )

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I'm taking him from the time of Gale of Darkness, which takes place five years after Colosseum, so I will be playing him at age 22. At this point, he's more laid-back and is prone to sarcastic joking, but it's largely a front for severe self-loathing and abysmal self-esteem resulting from his own failures and past mistakes, including his role in the Shadow Pokemon Project and his perceived cowardice at not doing anything about it when Cipher returned five years later. He's got a lot of guilt and trauma buried under his casual facade.