Dutch Van der Linde 𖦏

Dutch himself is shown to be a merciless killer who justifies killing innocent people or lawmen as a way of combating the corruption of the federal government. Despite his brutal ways, Dutch is educated and, unlike many outlaws, genuinely believes he is committing these crimes for idealistic reasons rather than greed. His anti-government and pro-individualist idealism, combined with his natural charisma, attracted a following of people who had been downtrodden by the society they lived in. Several members of the gang were orphans, minorities, town drunks, former prostitutes and other lowlifes; people who had felt they had no purpose until they joined the gang and Dutch gave them one. This created a strong sense of unity within the gang and a great sense loyalty to Dutch.

Despite at times being rather brutal in his methods, Dutch would often joke around with his fellow gang members and had a kind, playful disposition. He would often make motivational speeches to encourage the gang to come together in times of hardship while preaching that "loyalty" and "faith" were among the highest and most honorable tenets. Before Hosea's demise, he often consulted him and Arthur on important decisions, putting it to a discussion and vote between the three of them when deciding on the direction of the gang, demonstrating how much their opinions meant to him.

Dutch employed a highly flexible command system within the gang. At the peak of his power, Dutch displayed genuine compassion for his fellow gang members and treated them as family members in a way that made them feel appreciated. He complimented them on their resilience and ability, thanked them for their loyalty and their work, and saw to it that they were supplied, fed, and sheltered. His generosity endeared him to new members, many of whom had known little but harshness, pain, and struggle. His capacity to believe in others and help them believe in themselves was in turn reciprocated. Although he demanded that members give loyalty and do their share for the gang as a whole, he also encouraged them to be themselves as well as to make use of their free time to optimize their own talents and skill sets. At his best, Dutch commanded a balanced brand of leadership that not only required followers to have structure and discipline but also allowed them to express freedom and individuality. He had utmost faith in his gang to overcome almost any situation regardless of the odds and regarded his most capable lieutenants, such as Arthur Morgan and John Marston, as his collective ace in the hole. Moreover, he remained accommodating to members who hardly contributed to camp such as Uncle and Reverend Swanson, and kept them around, establishing the gang as more of a family than a business.

Throughout his life, Van der Linde demonstrated incredible courage, although by 1899, his fearlessness often overlapped into recklessness. Whether facing rival gang leaders, powerful men, or law enforcement, Dutch had no qualms with confronting any such opponent head-on, and in the face of imminent danger and gunfire, he often stood at the front of his gang. He displayed this courage most brazenly during the confrontation at Braithwaite Manor, where he approached the Manor that housed many gunmen, directly despite being in the line of fire and sought little cover during the ensuing firefight; and when confronting Leviticus Cornwall and his gunmen, whom he stood a mere gangplank's distance away from, having a simple conversation with before shooting and killing him on the spot.

The Pinkertons' relentless pursuit along with the constantly increasing pressure from civilization that the Van der Linde gang faced during its final months began to take a toll on Dutch and affect him. He became more driven by ego, money, and vengeance, beginning to outright despise anyone who questioned him. As his behavior grew more aggressive, violent and erratic, so did his plans. Dutch callously killed powerful figures like Angelo Bronte and Leviticus Cornwall, against Hosea and Arthur's warnings, solely out of vengeance with little regard for the outcome, starkly contrasting with his previous ideology that "revenge is a fool's game." His heists also expanded dramatically in scale and risk, launching a full-on assault on the Cornwall oil refinery and robbing a train carrying army payroll. These revenge murders and highly aggressive and destructive attacks attracted more attention from law enforcement and led to dangerous consequences for the gang as a whole.

After the disastrous bank heist in Saint Denis and Hosea's death, Dutch began to tighten his grip on the gang and took his valuing of loyalty to an utmost extreme, labeling anyone who questioned him as a 'doubter' and lessened the freedoms the other members of his gang once had. This made it easier for him to make flat and absolute decisions that decide the course of the gang without taking any input or criticism from those he led, making his leadership increasingly despotic. Unlike before, Dutch began to value Arthur's and John's opinions less and less as the two often criticized his decision making. Instead, Dutch consulted solely with Micah Bell, someone who never questioned his decision making and instead actively encouraged and loyally stood by him, no matter what. Whenever a member of the gang questioned Dutch's actions, he would immediately see such an action as traitorous and the person doing so as a threat.

Dutch commonly referred to John and Arthur as his brothers or sons, with Dutch himself and Hosea becoming fatherly figures to both of them, implementing a family-like relationship with the gang members that had stuck by him over several years. However, as Dutch became more erratic and paranoid, Arthur and John started to question his leadership and decisions, resulting in Dutch becoming increasingly resentful as well as suspicious of their motives. His paranoia and disdain for the "doubters" is shown when Dutch leaves both John and Arthur to die in two respective situations, as well as leaving John to be arrested by Pinkertons during the bank robbery in Saint Denis.

Dutch deliberately leaves Arthur to die while robbing Cornwall Kerosene & Tar. Upon seeing Arthur pinned-down by a soldier, Dutch flees the scene with only a quick glance. Dutch quickly denies this act minutes later when confronted by him. In John's case, Van der Linde was enraged that Marston wished to leave the gang with his family, believing it to be evidence of disloyalty. Dutch's choice to abandon an injured John, falsely report his death to the gang and denying it when confronted by him divulges his tendency to lose interest in underlings who do not follow him blindly. Years later, upon realizing that Marston never betrayed him after all, Dutch admitted to John that he made a mistake, but immediately and callously brushed off the betrayal by saying "I never claimed to be a saint".

Dutch's moral and philosophical hypocrisies can be observed as early as 1899. Despite being vehemently opposed to cultural, technological, and industrial progress, Dutch benefits the most from modern inventions out of any other gang member. His clothing is often far more elegant than anything else the rest of the gang wears (apart from Molly). He plays tracks on a phonograph within his tent and is frequently found reading at camp (the only gang member that reads more than he does is Mary-Beth). Actually, the fact that Dutch has such a well-developed philosophy to believe in and preach to his gang demonstrates a surprising level of intellect, philosophy and culture on his part; all of them prime examples of the very civilization he opposes.

By 1911, Dutch's underlying hypocrisy has become even more apparent; both his horse along with his revolvers have disappeared. Instead, they have been replaced by an automobile and a Semi-Automatic Pistol, and a well-stocked bookshelf and typewriter can be found in his lair in Cochinay. This hypocrisy is noticed and pointed out by Uncle, who once remarked that Dutch is not fighting for the right to pursue "a better life" as separate individuals with their own personal freedoms, but rather for what Dutch monolithically believes "a better life" is.[35]

A testament towards how much Dutch values loyalty can be seen in his relationship with Micah. During the final days of the Van der Linde gang, Micah became Dutch's most trusted consultant; unlike Arthur, Micah never openly questioned any of Dutch's actions, no matter what they were. This resulted in Dutch trusting in Micah so much, that when it was revealed that the latter was the Pinkerton spy, Dutch couldn't bring himself to believe it, even after Micah had shot and killed Susan Grimshaw in front of him. Not even Arthur repeating the truth with his dying breath would dislodge Dutch's disbelief, although it did have some effect as Dutch would abandon Micah immidiately after. It was only years later that Dutch would finally come to terms with Micah's betrayal and exact vengeance by shooting him.

By 1911, the once-idealistic rogue had fully deteriorated into a delusional maniac, sadistic and violent killer who was secretly aware that all of the horrible crimes he committed had changed nothing about the government or society. Fully embracing his love of violence, Dutch resorted to murder as his primary solution to problems, such as when he callously shot Muriel Scranton. His enjoyment of killing can be seen in "The Prodigal Son Returns (To Yale)", where when asked by John why he wanted to kill him and Professor Harold MacDougal, he simply replied "I don't know, sport, I guess."

In his final moments Dutch expressed remorse for his actions, likening himself to a monster and telling John that he couldn't stop fighting for his ideas despite the futility of it, lamenting that he was unable to fight the nature of a changing world and simultaneously, he couldn't fight the nature of himself to stop. Before committing suicide, Dutch told John "Our time is passed". This signified, at long last, his final acceptance that the Old Wild West and the way of life it once stood for had come to an end and his will to live along with it.