I think that, in a lot of ways, the Red Dead series is about Jack Marston's development as a person, and I'd absolutely play a game that put him into the time of infamous bank robbers like John Dillinger and Baby Face Nelson. (He'd be a little old by that time, but it could work.) While I do think he might've escaped the outlaw life, I feel that, like his father, it may be too deeply ingrained in him to ever fully escape.

Also, (to me, at least,) a prequel about the Van Der Linde gang would work more as a prequel. I haven't played that much RDRO, but it makes sense that that would be the proper place to put the story of the pre-Massacre gang, and frankly, I just don't see Rockstar going back to the proverbial prequel well for another full game.

@Wagwan piffting23 I wouldn't really say a prequel has any potential, as we already know everything about the Van der Linde gang's past, especially it's formation. Dutch and Hosea meet each other one night in the late 1870s, decide to team up, and act as a conmen duo for a few years. Later, they come across an unruly 13-year-old boy named Arthur Morgan, and the trio set out to take from the rich and give to the poor. Over the next two decades, they come across many other lost souls of equally ragtag and simplistic backgrounds. That's literally it. You can't write a story out of that without adding excess detail and filler that would further prove how pointless the story is. If a prequel only exists to show off things that we already exactly how they happened, then it has no reason to exist at all.

"With a prequel, they could include the backstory for many of the characters where we play as them. For example, we could use Javier when he’s escaping Mexico and find out more about what he was doing there. Similarly with a Bill in the Army and Micah saving Dutch’s life, or the background of the Callander brothers. We could also find out about the traitor, or any other gang member who had died prior to the Blackwater Massacre."

^Most of the members of the gang, especially the ones with any backstories at all joined within no more of a five-year interval of RDR2 (Bill, Javier, Sean, Micah, Lenny, Charles, Jenny, Mary-Beth, Tilly, etc.), so you can't have it take place in a game about the formation of the VDLG in the 1870s (making an open world game taking place over the span of twenty years is a recipe for disaster), and making a game taking place only a few years before the RDR2 seems pointless. Moreover, all of these backstories are purposely simplistic and uninteresting; meant to exemplify how most of these characters don't have a tragic backstory; they're just broken people beaten down by a cruel world, full of unfairness. They don't have some tragic backstory, they are simply insignificant victims, and they joined the game to feel as if they are a part of something. A story that can be accurately summarized in less than three sentences isn't something that should be given any more attention than a place as a campfire story.

"Jack’s story is completely dead. RDR 1 ends on a cliffhanger, and so making a story about his later life would ruin that. In addition, it’s no longer the Wild West."

^I'm not disagreeing with you on that - but at least a story about Jack is something new, something original, something with new locations and with new characters rather than just bringing the RDR2 cast back from the dead. At least it's something at all, rather than just a visual retelling of stories we've heard countless times.

@Phoenixskull295 
[M]aking an open world game taking place over the span of twenty years is a recipe for disaster...

This is probably true, but it also makes me all kinds of nervous about GTA 6...

As Cool as option A would be I honestly don’t think it’ll happen. Rdr2 is already post-rdr1 so I doubt they’ll do it again

A Mafia game with Jack would be okay, but not a western that is set beyond 1914.

@Phoenixskull295 Regarding the latest offers. As much as everyone would like to know the exact description of Jack's fate after 1914, I do not think that this will be a good plot basis for the next part of the series. For understanding; Jack's adult life will take place after the end of the era of the wild West and the frontier, which will clearly affect the nature of the story and its escposition, and the story will be played like GTA, which will not please everyone because Red Dead is not GTA. The story itself will not be complete and rather meaningless, because Jack, not without the help of his father, did not want to become a criminal, and even more so not to form his own gang. Jack also would not have gone to the front of the first world war because he himself hated government agencies and the service because of the events of 1899 and the death of John, so becoming a soldier in the US armed forces would be a complete contradiction in the context of his formed position and history. Most likely, Jack became a writer because of his love for books, which is hinted at though uncanonical but easter egg in GTA 5. It is better to leave Jack untouched for further games in the series.

@DonaldTrump15 I’m not disagreeing with you, I’m simply trying to stress how a prequel about the formation of the Van der Linde gang is even more pointless.

Neither. Rockstar has fully fleshed out the Van Der Linde legacy. A Jack game wouldn't be a wild west game and we know about the beginning of the Van Der Linde gang. Rdr2 made so many interesting characters that would be a good main character. Like Black Belle. But if they make a game it should be like after the Civl War but before 1899 since that was the height of the wild west.