Dutch Van der Linde’s long-standing feud with Colm O’Driscoll got the Van der Linde gang into trouble on more than one occasion during the events of Red Dead Redemption 2. Given the hostility between the two gang leaders, it may seem counter-intuitive that both of them were once in business together, but their feud was one that was born out of years of friendship and camaraderie.
When Dutch first started getting involved in a life of crime, he became acquainted with Colm, leader of the infamous O’Driscoll gang, who the Van der Lindes would later come to rival. Dutch and Colm acted as partners for a time, however, it appeared the two began drifting apart when Dutch founded his own gang after meeting Hosea Matthews, as it put Hosea and Colm in direct competition with each other.
Eventually, tensions became so high between the two of them that Dutch killed Colm’s brother (whose name is not mentioned in Red Dead Redemption 2's story). In revenge, Colm killed Dutch’s girlfriend, Annabelle, which set the stage for a years-long blood feud not only between the two men but their rival gangs, which explains why the outlaws come into so much conflict with each other over the course of RDR2.
Why Annabelle Was So Important To Dutch Pre-RDR2
Dutch is portrayed as quite the ladies’ man throughout Red Dead Redemption 2, but it’s implied that Annabelle had special significance to the outlaw and that her death took a great toll on him emotionally. Annabelle is referenced a few times during the course of the game. For instance, a bitter piece of dialogue between Dutch and Colm sees the O’Driscoll leader admit he didn’t like his brother all that much. To this, Dutch sneeringly replies that he did like Annabelle, explaining why Dutch is never willing to put the long-standing feud behind him. She’s also referenced by other characters like Hosea Matthews, Arthur Morgan, and Jamie Gillis, Mary Linton’s brother. When Arthur goes to fetch Jamie for his ex-girlfriend, the young man will say that it was likely a good thing Arthur’s relationship with his sister didn’t work out upon learning that Annabelle is dead.
In the end, Dutch never manages to avenge Annabelle’s death. He’s eventually killed by his former gang member, John Marston, who was being blackmailed by the Pinkertons. Colm meets a similar face, interestingly enough, as he was arrested and hanged by government forces. The Van der Lindes did all they could to make sure the O’Driscoll leader’s acquaintances didn’t break him free. There’s a long, complicated history behind the dispute between Red Dead Redemption 2’s Dutch Van der Linde and Colm O’Driscoll, but in the end, the feud died with them.