The story of Red Dead Redemption 2 is one of failure. As the game's narrative unravels, failure becomes the defining factor of both the Van Der Linde gang and Dutch, the enigmatic man who leads it. Despite the gang's faith in Dutch's intelligence and charisma, his rash behavior and the deterioration of his moral center sends the gang into a downward spiral which proved inescapable even as he insists on his ability to save the gang and earn their freedom with just "one more score." Dutch always has a plan, but they never seem to go right.
[Warning: Spoilers for Red Dead Redemption 2 below]
As with many tragic stories, the separation of the Van Der Linde gang in Red Dead Redemption 2 began with a singular event which acted as the turning point for their downfall. This offscreen event, known as the Blackwater Massacre, is the initial blow which sends the Van Der Linde gang reeling against the ropes. What was originally supposed to be the smooth heist of a ferry carrying considerable funds turned into a bloodbath, as Dutch's gang was attacked by a small army lawmen. The heist itself had been a risky undertaking from the onset, and in the resulting chaos Dutch steers away from the gang's benevolent, Robin-Hood code of ethics by brutally murdering an innocent woman. Multiple members of RDR2's gang are killed or captured in the gunfight, and the weakened crew was forced to stash the money somewhere secret and flee towards a nearby mountain range. With the help of a snowstorm they shake their pursuers, but the weakened gang is stuck in a blizzard with a paranoid, ruthless leader at the helm.
This unseen intro is important because it illustrates why exactly all of Dutch's subsequent plans fail in Red Dead Redemption 2. He always underestimates the risks associated with high-stakes jobs. Dutch believes he and his gang are somewhat invincible, and when they are put into a desperate situation where they have no options but to run, Dutch's sense of morality cracks. He begins acting ruthlessly, leading the gang to lose trust in him. With every failed robbery or con, Dutch attracts more enemies for the Van Der Linde Gang. These new enemies inevitably interfere with the next plan he hatches, dooming whatever small chance his plan had of succeeding.
RDR2: Dutch's Failure At Horseshoe Overlook
Things only get worse for RDR2's Van Der Linde gang as they proceed, even once they make it out of the mountains. As the blizzard lets up, they run another high-stakes heist on a train owned by the affluent Leviticus Cornwall. Once they have a bit of funding, the gang moves to a new location, but their desperate train robbery attracts bitter attention from Cornwall, who sends agents from the Pinkerton Detective Agency to track the Van Der Linde gang.
During this par of Red Dead Redemption 2's story, Dutch is unable to lay low. Recognizing the approaching oppression of modern industrialization, Dutch spends the entire game scrambling to earn the gang money in whatever way he can. He repeatedly involves the gang in various high-profile escapades which attract more attention. Eventually, the Pinkertons do catch up to Dutch in the town of Valentine, forcing him to make an escape and relocate the gang to a new hideout.
RDR2: Dutch's Failure In Lemoyne
Dutch leads the gang moves further south until they reach the town of Lemoyne, where two families are embroiled in a long-lived and bitter feud. The two families, known as the Grays and the Braithwaites, are venerated and wealthy clans, leading Dutch to play both sides in the hopes of extracting wealth from both of them. This does not go well for very long as the gang carries out various conspicuous sleights both for and against each family.
Fairly soon after their arrival, both the Grays and the Braithewaites realize they are being played. In retaliation, the Grays ambush the gang and kill one of their key members. Then, the Braithwaites abduct the son of John Marston, protagonist of the first Red Dead Redemption, and sell him to another wealthy individual named Angelo Bronte from the city of Saint Denis.
RDR2: Dutch's Failure In Saint Denis
The Van Der Lindes eradicate the Braithewaite family and burn their home to the ground before leaving Lemoyne for Saint Denis. They track down Bronte and retrieve John's son, but Dutch insists on furthering the gang's involvement with Bronte in the hopes of getting enough money to escape and earn their freedom. Bronte directs them to rob a trolley station where a sizeable sum of money is being held. This Red Dead Redemption 2 mission turns out to be a red herring, as the station held no money.
Dutch then becomes intent on staying in Saint Denis, wanting to make a move against Bronte and rob the city's bank. The gang successfully infiltrates Bronte's mansion, and Dutch drowns him and feeding the body to an alligator. The gang then proceeds to rob the largest bank in Saint Denis, but the job goes south when Pinkerton agents interrupt. As the gang escapes, multiple major gang members are killed, including Dutch's co-leader, Hosea. Dutch and several other are unable to reach camp, so they board a boat which gets hit by a storm and washed up in Guarma. After escaping Red Dead Redemption 2's island, Dutch relocates the gang one final time before it all finally falls apart.
RDR2: Dutch's Failure At Beaver Hollow
Now holed up in a small woodland cave, the Van Der Linde gang is at the end of their rope. Multiple important gang members have died, the Pinkertons are hot on their trail, and RDR2 gang is still no closer to freedom. Several members have abandoned the crew, and those who are left suspect a traitor in their midst. The protagonist, Arthur Morgan, suspects Micah. Despite this, Dutch holds resentment towards several members of the gang, including John and Arthur, leading him to lose trust in both.
At the same time, Dutch murders Cornwall and makes another enemy for the gang, as he involves himself in a conflict between the U.S. Army and the Wapiti Indian Tribe. During a robbery on an Army train, John Marston is seemingly fatally shot, and Dutch leaves him for dead. When Marston returns to the camp alive, his presence ignites conflict throughout the gang as Pinkerton Agents close in on their position. Dutch continues to favor Micah's word over John and Arthur's, and so he pursues them until the Pinkertons intervene. This event marked the official end for the Van Der Linde gang.
At this point, Dutch's continual failures have piled up beyond reason. Every plan he thinks of proves itself to be rashly considered, and with every Saint Denis bank robbery, Braithewaite-Gray scheme, and Blackwater Massacre, the gang attracted more attention to itself, further hindering their ability to establish a life of freedom for themselves.
During Red Dead Redemption 2's ending, when Micah chases down Arthur and both are left badly beaten, Dutch finally realizes how his mistakes have caused the gang to fracture. He abandons both Micah, whom he now knows is the rat, and the dying Arthur. Because Dutch failed to carefully consider his plans while failing to uphold his moral code, the Van Der Linde gang became his greatest failed plan. The life of freedom sought by nearly every character in Red Dead Redemption 2 proved itself as a lost cause, because they were being lead by an irresponsible and impatient leader.