Such A Good Analysis/theory.

Such a good analysis/theory.

"That Jimmy isn’t as dumb as he looks."

Jimmy Brooks is one of the first characters we can choose to kill or to let live after being dumb enough to confront Arthur about seeing him in Blackwater, other than that one encounter, we can find references to him two different places throughout the game, which might lead to something interesting going on.

The most commonly known other place to find Jimmy Brooks is in the strange man's cabin where two different poems can appear depending on if he is killed or not. "There was a man called Jimmy Brooks, Who was always running into crooks, Till one chased him down, And he had to talk his way round, That Jimmy isn’t as dumb as he looks." Now this points is strange, him not being as dumb as to just recklessly point out a killer. Though it could refer to him being able to talk his way out, I wouldn't say that anything he said saved him, him being saved is completely depending on Arthur. I feel that we as a player already have an idea about if we will kill him or not before he starts very badly pleading for his life.

The second place, a lesser known place, in which you can find Jimmy Brooks, is on the register stone a little outside of Cornwall Oil and Tar.

"J. Brooks. US Post 63." (Confirmed to be about him)

Now the person we saw in Valentine looks about thirty, but this was made 36 years ago and I doubt he worked in the US post when he was like four, and I will not put him in his mid fourties, same age as Dutch.

These two instances alone can be explained logically, however when dealing with anything related to The Strange Man, you can allow yourself to think a bit more.... Unlogically, magically if you will.

The Strange Man is sometimes seen as Death and the time after the Blackwater Masacre is often seen as marking Arthur's last time leading to his inevitable death, and with it approaching, Death might want to see what kind of person he is dealing with.

Jimmy Brooks is one of the first times that Arthur's honor is affected, a trial of Arthur's character, and it wouldn't be the first time that The Strange Man tests the morality of people he knows is dying, he does the same to John in rdr1, sending him out to rob Sister Calderón or stop a man from cheating. The only difference is that John has to go to the trial whereas the trial is presented to Arthur. However it can simpily be that The Strange Man is adapting the challenges to the people.

Arthur's trial is one of life and death, John's aren't. The ones John gets are more about his morals about life rather than death. Encourage a man to cheat, or tell him he is better. Rob the sister, or donate to her.

Both of the negative things John can do are... Negative, but they aren't that bad. Encouraging a man to cheat is just bad moral but not illegal, and robbing a sister is illegal but you can gain something from it, thus you would choose to go there even if you had the choice not to.

Arthur's on the other hand. It would be better for Arthur to not at all encounter Jimmy, stealing a horse and chasing after him through an entire town is bound to draw attention, and afterwards killing him not far from said town, is not optional, even if you save him, you have drawn attention to yourself. If Arthur's trail was optional, he would not take it thus it is forced upon him.

There is also a reason why The Strange Man appeared for John but not for Arthur and it is all about their redemptions.

Arthur's redemption comes from inside, he doesn't care what others think about him, only what he thinks about himself, and until he changes his mind about himself and everything he does, nothing can even sway him. He thinks he is a bad man, nothing can change that until he himself changes his perspective. He doesn't need The Strange Man telling him "you have done bad" because he knows and he is suffering for it already, he needs to be shown he can be a good man.

John on the other hand, his redemption comes from the outside, he doesn't change because he wants to, he changes because the world needs him to. He doesn't care about what he did or who he killed and he doesn't need to prove to himself that he is a changed man, he needs to show the world that he is a changed man, that is the only way he will be left alone. However The Strange Man is there to remind him why he hasn't been forgiven yet, because he killed many and he needs to be reminded of it.

Now who is Jimmy Brooks then? Well, he can just be a random man who looks young for his age and was influenced by The Strange Man to do what he did, but he could also be dead. It is a solution to him being old enough to work with the US Post in 63 and being in his thirties in 99.

He died sometime after 63, when he was in his thirties, and then when Death (The Strange Man) needed Arthur's morals tested, he didn't want to put an living person's life on the line, as it was not their time to die, so he used a person who was in fact already dead.

Anything with The Strange Man is possible.