The Red Dead Redemption series is one of the most tragic in all of gaming. Both stories are about men trying to redeem themselves after a life of crime and debauchery, and both end in tragedy as they are respectively killed.
To make matters worse, the rest of the games are also littered with untimely and sorrowful deaths. Despite their natures as criminals and outlaws, we can't help but feel attached to them and their stories, and when they die, we feel it. We hate ourselves for feeling it, but we feel it all the same. These are the ten most tragic deaths in the Red Dead Redemption series, ranked.
10 Javier Escuella
Escuella served as a major antagonist in the first Red Dead Redemption, but his character was given significant depth in the prequel. He was an active member of the gang and was even quite close to Arthur, as the two bonded over fishing and horse stealing. You actually start to like him...until you accept the inevitable. He eventually sides with Dutch and Micah and flees with Bill, leading into the events of Red Dead Redemption. In that game, you have the option to kill Javier, and if you do, John will look at his corpse with a tear in his eye as he remembers the good times.
9 Sean MacGuire
Sean was arguably the gang's funniest member. Well, Uncle is pretty darned funny as well, but we're talking intentionally funny here. That said, he admitted into the gang after trying to rob Dutch. However, his life is brought to a very swift end in Rhodes. While accompanying Arthur, Bill, and Micah on a job in town, Sean is shot in the head while absently walking down the street. It comes out of nowhere, and while it's certainly sad to see the comic relief go, it's more surprising than anything...
8 Hosea Matthews
Hosea helped create the Van der Linde gang alongside Dutch, and he often serves as the voice of reason against Dutch's more dreamy and ambitious ramblings. Despite his reluctance, Hosea continues to go along with Dutch's insane schemes, although it tragically costs him in the end.
During the Saint Denis bank robbery, Hosea is captured and held prisoner by Agent Milton. After talking to Dutch through the door, Milton shoots and kills Hosea, placing the blame on Dutch's feet. And we mean, he's not exactly wrong...
7 Lenny Summers
Lenny is one of the most tragic characters in the entire series. He is the son of a slave, and his father raised him well. However, he was eventually beaten to death, and Lenny killed his father's murderers in an act of revenge. This caused him to go on the run and he eventually made his way into the Van der Linde gang. Arthur and Lenny grow close throughout the course of the game, but he is tragically killed during the Saint Denis bank robbery. He was one of the gentler members of the gang, and his death served as a turning point in the tone of the story.
6 Kieran Duffy
We loved Kieran. He was a man simply caught up in the wrong place at the wrong time, and it cost him. He was given an ultimatum by the O'Driscoll gang, and his inclusion in said gang resulted in the Van der Linde group treating him like a traitor. However, Arthur realizes that his loyalties aren't actually with the O'Driscolls, and the two grow weirdly close once Kieran saves Arthur from death. He certainly didn't deserve his brutal death - kidnapped, tortured, and eventually decapitated. His headless corpse is sent back to Shady Belle, and it serves as a major blow to the gang's, and especially Arthur's, morale.
5 Molly O'Shea
The person most negatively affected by Dutch's downfall is arguably Molly O'Shea. In the beginning of the game, Dutch and Molly are lovers and can be seen engaging in loving activities like slow dancing. However, their relationship quickly begins to deteriorate thanks to Dutch's prolonged absences, lack of attention, and increased paranoia. Before long, Molly becomes a drunk who essentially commits suicide by falsely admitting to the gang that she betrayed them and talked to the Pinkertons. It was a quick way out for a life that had long gone tragic.
Uncle was always one of the kindest and gentlest members of the gang. He mostly just sat around, got drunk, and complained about his lumbago. He eventually retires with John and lives with his family on his ranch, seemingly content to live out the rest of his days in peace. However, he is caught unawares by the soldiers and Bureau agents that storm John's ranch, and he is shot in the chest by a soldier. John thanks Uncle for his protection as he dies, a wonderful moment that proves that Uncle and John really were family at the end of the day (despite all the bickering).
3 Dutch van der Linde
Despite serving as the primary antagonist in both games, you can't but feel a little sorry for poor Dutch. In RDR II, he is actually quite happy at times and seemingly wants nothing more than to keep his "family" together.
However, his mental health slowly begins to deteriorate as the law and "civilization" closes in, and he grows increasingly violent and erratic. He eventually accepts that change is inevitable and throws himself off a mountain, both to avoid capture and commit suicide. His death didn't mean much in the first game, but is given incredible weight and tragic heft after witnessing the events of RDR II.
2 Arthur Morgan
Morgan's death is certainly tragic. He was much more evil than John ever was, but he also redeemed himself in a much greater manner. His quest for redemption begins after being diagnosed with TB, and the disease slowly wastes away at his mind and body. He eventually dies after fighting for John and allowing him to escape. Luckily, we had time to accept his diagnosis and expect his eventual death, which is more than we can say for someone...
1 John Marston
John's death is undoubtedly the most tragic of the series. For one thing, the death comes out of nowhere. While we all accepted Arthur's eventual demise, John's death at the hands of Ross comes as a major surprise and story twist. His background was also more tragic than Arthur's. He actually got out of "the life" but was tragically sucked back in after seeking revenge on Micah. If he didn't do that, he wouldn't have died. He just wanted to avenge the man who saved his life and it ended up costing it...