Many of the death scenes in the game felt more shocking to me than saddening. Arthur’s actual death didn’t quite evoke a lot of emotion because heading into the game I already figured he would probably die. As for evoking sadness, the scene where Arthur is talking to Sister Calderon at the train station really got me. Right when Arthur said “I’m afraid”, and you could see his eyes watering, I really felt my eyes watering too.

It’s not the FBI who shoot him; it’s mainly the US Army, along with Edgar Ross and a few US Marshals.

As for the saddest moment, it’s hard to say. Possibly Eagle Flies, especially after he had been manipulated and his people had not been saved. The circumstances around it like that made it more chilling. Other than that, the death of Arthur, his horse and the last ride are also notably sad moments. A tie between these two, for me.

The gang splitting apart is, to me, pretty depressing. Not for the whole "farewells and deaths" and everything, but the realization that Dutch worked to have a gang of his own, this gang, only to just.. break. And it was all because of Micah.

The attack is orchestrated by the Bureau of Investigation (BOI) - which later became the FBI - but the people who shot John were mainly US Army soldiers (on the Bureau’s orders).

Don’t believe everything you read on Google.

Surprisingly enough, I actually think it’s Lenny taking a bullet. Earlier I probably would’ve said the gang splitting up, but after I finished the game, I’ve actually started to think about Lenny’s death, and how different it was than any of the others. Every death in red dead seems to be build up in a certain way or they have some sort of conclusion (like cutscenes or journal entries) but the way they handle Lenny’s death seems so different at least to me. How sudden it happens and the fact that it’s during gameplay. And when he’s shot they don’t have time to mourn or even react. Arthur stays behind for a second, but continues to run with the others. And to me that tells a lot about their relation, how much Arthur liked Lenny and admired his optimism and way of thinking. And since Lenny is a character close to Arthur it may seem weird that his death is brushed off so quickly, but I think I understand why. It’s a little similar to Seans death - both their deaths were very unexpected - but that just makes it more real, more unfair. How quickly they are taking away from life in their young age and how Arthur doesn’t even get to mourn, but is instantly tossed into action. I dunno if this makes any sense at all, but, yeah, I think Lenny’s death is the most heartbreaking of them.