Dutch and Hosea had been close friends since 1878. The two went on to form the Van der Linde gang together. Hosea’s relationship with Dutch became somewhat tested, as Hosea’s preference for non-violent ways of making money (such as scams) began to clash with Dutch’s increasingly lofty and unrealistic robberies, as well as his increasing preference for violence. Despite this though, Dutch held Hosea in very high regard, allowing his judgement (as well as Arthur’s) to be given the same weight as his own in important gang decisions, notably when deciding whether to go ahead with the Saint-Denis bank robbery. Hosea’s death shook Dutch, who never really recovered from it, and it was possibly one of the causes of Dutch’s descent into insanity.
Dutch essentially raised Arthur, teaching him how to ride, shoot and read (amongst other things). The two had become very close, with Dutch often referring to Arthur as his “son” or “brother”. After the failed Blackwater boat heist, Dutch says to Arthur “You’re the only one I can rely on to stay strong right now”, indicating that he believed Arthur was the most loyal and trusted of all his gang members, maybe even surpassing Hosea. Dutch also regularly praised Arthur for his work in the gang, and also seemed to enjoy spending time with him. Dutch also seemed to fully trust Arthur and his judgement, giving him (along with Hosea) the same influence as himself in gang affairs, demonstrated before the Saint-Denis bank robbery.
However, as Dutch slowly began to lose his sanity, Arthur began to question Dutch, losing faith in his mentor for the first time. Dutch quickly picked up on Arthur’s doubting and, in response, began to question Arthur’s loyalty. Arthur’s declining relations with Dutch were exacerbated by the growing bond between Micah and Dutch. Arthur was extremely suspicious of Micah, seeing him as a bad influence on his mentor. In addition, Arthur’s tuberculosis and subsequent wish to help John escape the gang with his family (in order to do one good thing in his life before he died) and the resulting bond between Arthur and John caused relations with Dutch to deteriorate further, especially as Dutch also saw John as a “traitor”. In the battle against the US Army with the Indians, Dutch seemingly left Arthur to die, believing that a “disloyal“ Arthur was no longer any use for him. After Arthur revealed that Micah was the true traitor, Dutch was in denial, unwilling to believe his protége’s allegations that Micah could possibly be disloyal. He sided with Micah, holding Arthur (and John) at gunpoint, probably with intention of killing them. Although this did not happen thanks to Pinkerton intervention, Dutch and Arthur would meet one last time when Dutch broke up the fight between Arthur and Micah. After Arthur reiterates that Micah is the true traitor, he is abandoned by Dutch. Although Dutch then knew that Arthur wasn’t the traitor he suspected, he would rather believe that Micah wasn't the traitor rather than think of himself as a failure. Ultimately, Dutch seemed more interested in Arthur’s loyalty rather than him personally, and his bond that he and Arthur previously had was likely as a result of Arthur's unquestionable loyalty. Although he resented the constant questioning and doubting, Dutch still held Arthur's words in high regard, which is clearly shown when he was told and pleaded to from a dying Arthur that Micah was the traitor all along. His saddened expression and decision to leave Micah cements this idea, and shows that he still respected Arthur.
In the Epilogue, it is seen that Dutch reunites with Micah to finally retrieve the Blackwater money. It is widely assumed that Dutch had shown up a few moments prior to John's arrival on the mountain because he too had planned on killing Micah for his betrayal 8 years ago, possibly as an act of redemption.This idea is supported by his conversation with John in the last mission, where he says "Same as you, I suppose." - [in response to John's question about why he was there at the time]. As their confrontation with John commenced, Dutch ends up shooting Micah and mortally wounding him, thereby implying that he regretted not acting on Arthur's request to kill Micah beforehand.
Dutch took John under his wing at a young age, teaching him how to read and shoot (along with various other things). John became a favorite of Dutch, with some considering him to be Dutch’s “golden boy”. John left the gang for a year to get away from his family soon after Jack was born, but was welcomed back by Dutch with open arms, showing the bond between the two. On top of this, Dutch frequently referred to John as ”son” or “brother”.
Despite Dutch liking John for the vast majority of his time in the gang, he eventually became concerned that Abigail was “poisoning” John against him. During the Saint-Denis bank robbery, John is captured and sent to Sisika Penitentiary, where he was sentenced to hang. Dutch, however, refused to rescue John, believing him to be a doubter and a traitor who he no longer cared for. During the final train robbery, Dutch once again left John to die, preferring if John was dead. When John appeared during a standoff at Beaver Hollow, John sided with Arthur against Dutch. Dutch held Arthur and John at gunpoint with the likely intention of killing them. Due to the Pinkertons attacking the camp, the gang was forced to flee and John would not see Dutch until 1907, eight years later.
The next time they met was on Mount Hagen when John prepared to shoot Micah (who was held at gunpoint by Sadie) but was interrupted by Dutch, which resulted in a three-way stand-off between Dutch, Micah and John. Dutch initially appeared to be on Micah’s side and criticized John for only thinking of himself and his family during the final days of the gang. Eventually, however, Dutch decided to shoot Micah, the true rat of the gang, before leaving and ignoring John’s attempt to thank him, likely showing that he still had a grudge against John. He also consciously leaves the Blackwater money behind for John and Sadie.
John and Dutch would meet again in 1911, where John needed Dutch dead in order to see his family again. Dutch caught John spying on his hideout in Cochinay, and responded by shooting the binoculars out of John’s hands, implying that he didn’t want to kill his former protége, even when he was working for the enemy. During the Blackwater bank robbery, Dutch mocked John for thinking he was better than him morally, before killing his hostage and escaping. When Dutch was confronted by John when his hideout was attacked, he attempted to kill John by using a machine gun. When this failed, Dutch was cornered by John, and then killed himself by falling off a cliff, which John preferred, as it meant he didn't have to kill Dutch himself. Even though Dutch had now fully transformed into a deranged maniac, John still had respect for his mentor and is seen sorrowfully looking at Dutch’s corpse.
The two initially had a loose friendship, although it quickly ended when Dutch killed Colm’s brother and, in retaliation when Colm killed Dutch’s lover Annabelle. This led to the start of a bitter rivalry between the O'Driscoll Boys and the Van der Linde Gang. The two hated each other with a passion and Dutch was even willing to abandon his principle of revenge being a “fool’s game” to hit back at Colm. Dutch enthusiastically helped to ensure that Colm’s hanging would go ahead, sabotaging a rescue attempt and seeing Colm O’Driscoll swing.
Like the rest of the gang, Dutch saw Bill as being dumb and prone to making the wrong decisions due to his lack of intelligence. He reprimanded Bill for starting a fight at Valentine saloon, for example. Despite this, though, Dutch also knew that Bill was deeply loyal and recognised him as one of the core gang members. Bill never lost faith in Dutch, and, despite always having an ambition to start his own gang, his loyalty to Dutch was uncompromised. He can sometimes be heard expressing his admiration for Dutch around the campfire at night, and did not hesitate in siding with his mentor against Arthur and John during the standoff.
It is thought by Arthur that Javier the most loyal gang member of them all. John later said that, when Dutch went mad, “Javier took it harder than any of us”, supporting the idea of Javier being extremely loyal. In return for being so loyal, Dutch liked Javier and was pleased to have him in his gang. When Javier was shot while trying to escape the local military on Guarma, Dutch pledged that he would come back to rescue him, telling Javier to “keep faith”. Dutch kept his pledge and helped to rescue Javier from his cage, even when it meant putting the gang’s escape in jeopardy. Despite witnessing Dutch killing Heidi McCourt during the Blackwater boat heist, and Dutch’s ever-decreasing sanity, Javier never lost faith in Dutch and sided with him against the “doubters”, Arthur and John, during the gang’s standoff.
Micah saved Dutch's life and Dutch seemed to take a liking to him (as opposed to virtually all the other gang members). Dutch followed Micah’s idea to undertake the Blackwater boat heist, against the wishes of Arthur and Hosea, Dutch’s two most trusted lieutenants, possibly showing how much sway Micah had in Dutch’s decision making. When Micah was imprisoned in Strawberry, Dutch referred to Micah as a “fine man” and was very insistent on him being rescued. After the ill-fated Saint-Denis bank robbery, Micah became Dutch’s sole lieutenant, with Dutch gradually trusting Micah more than Arthur, mainly due to Micah agreeing to his every decision and therefore being “loyal”, as opposed to Arthur’s growing doubts on Dutch’s leadership. Dutch and Micah would then work together privately to plan the gang’s final train robbery. When Arthur reveals that Micah was an informant for the Pinkertons, Dutch seemed to be in denial and unwilling to accept that someone so “loyal“ could possibly have betrayed him. Dutch eventually realizes that Micah was the real traitor after the fight between Arthur and Micah, and abandons him, signaling an end to their friendship. In 1907, during a standoff between Dutch, Micah and John, Dutch (even though he believed that John was disloyal in the last days of the gang and initially appeared to be on Micah’s side) shot Micah, revealing that he had fully come to terms with Micah’s betrayal and likely wanted revenge as much as John, Sadie and Charles did, for bringing down the gang that Dutch had devoted his life to.
Lenny was a key gunman for the gang and was praised by Dutch, most notably due to his high ambition and ability to handle his own in a fight. Although Dutch initially planned on choosing Micah as the third gunman for the Trolley robbery, he ends up taking Lenny after Arthur's insistence. After the Trolley heist, Dutch grows to have a lot of respect for Lenny after seeing how well he was able to handle himself with the odds laid against them. During the Saint Denis bank robbery, Lenny is gunned down on the roof, much to Dutch's dismay. Dutch seemed devastated, but didn't have much time to react due to the Pinkertons ongoing assault. Lenny's death ultimately affected morale in the gang, and caused some to quickly lose hope.
Upon discovering Sean is captured by bounty hunters from Trelawny, Dutch agrees with Arthur that they "must" rescue him. Whether this is due to a "No Man Left Behind" complex, or due to Dutchs' respect/admiration for the boy, is unknown.
Charles was an exceptional hunter and gunman for the gang, initially believing in Dutch's goals while being fond of his individualist ideals and non-prejudice views based on race. Their relationship begins to significantly deteriorate during Chapter 6, when Dutch becomes more erratic and manipulates Eagle Flies into starting another war with the US Army so that attention would be driven off from the gang. Charles eventually decided to opt in staying at the Wapiti Indians Reservation rather than returning back to the gang, showing that he lost his faith in Dutch and that he was not a man worth following any longer.
It seems he has some level of respect for Sadie, seeing as he refers to her as "Mrs. Adler" throughout the game, and entrusts her to ensure Colms' death.
It is mentioned that Dutch never trusted Kieran after his defection from the O'Driscoll gang. He believed that Kieran would be the most likely candidate to betray him and did not include him in important gang affairs, instead leaving him to look after the camp alongside the women. If Arthur decides to go fishing with Kieran, he will describe his place in the gang as a "No-Win Situation". After Kieran's death, Dutch feels sorrowful and will mention his name along with the other members that passed. Whether these words were simply for presentation or he actually meant it is up for debate.
Much like the rest of the gang, Dutch felt pity for Reverend Swanson, but also berated him for his lack of contributions. Although he seems to want to cut him loose, Dutch never does so, possibly due to the fact that the Reverend once saved his life in the past.
It seems that Strauss takes up little space in Dutchs' mind, seeing as he didn't realize Strauss was gone, unlike some other members that left. It seems he finds Strauss irritating, seeing as he told Arthur he wanted "Blow his brains out" after talking to him.
Molly was Dutch's most recent lover although it is implied he wants to move on from her. Despite this she did love him as she left a rich life in Ireland to be with him. Due to the growing pressures of being such a wanted man, Dutch continually ignored her which made Molly ever more desperate for attention. Eventually, she confesses to being an informant for the Pinkertons, which causes her demise. It is later revealed by Agent Milton that, even though Molly was in his custody, she said nothing and therefore stayed loyal to Dutch.
Susan was a past lover of Dutch before he moved on to Annabelle. Despite this he still trusted her to efficiently run his camp, and look after Arthur after his escape from the O'Driscolls. During the standoff at Beaver Hollow, Susan is shot dead by Micah, to which Dutch seems unconcerned. Whether this is because he thought that Susan was another “doubter”, or because of his bond with Micah, is up for debate.
Karen and Dutch seemed to be on good terms, as she acted as a gun-woman, con-woman, and occasional caretaker for the gang. She is very capable of planning robberies as seen with the successful Valentine Heist, and seems to have no trouble manipulating others for her own benefit. During Chapter 6, Dutch and Karen have minimal interactions, though it can be assumed that she took up little space in his mind as he does not comment on her intensifying drinking habit.
Dutch and Tilly have minimal interactions throughout the game, though it can be broadly assumed by most players that they had a good relationship prior to Chapter 6.
Dialogue during their interactions implies that he wants to start a relationship between him and her as he starts flirting with her during chapter 3.
Dutch most likely has some respect for Josiah, due to the fact that they are both conmen (despite their different methods,) and he trusts his leads to be true.
Dutch often makes fun of Pearson much like other members. He trusts Pearson to be in charge of the Gangs rations, but whether this is due to a lack of a more qualified professional, is unknown.
Dialogue between the two alludes to him being in a relationship with her, much like many other members of the Gang.
Much like the other men of the gang, Dutch acts as an uncle to Jack, and provides guidance to him.
Dutch had a soft spot for Uncle, most notably due to his sense of humor and ability to entertain the gang. During Chapter 6, it is unknown as to whether Dutch still felt this way due to the very minor interactions shown between the two, though his constant paranoia indicates that he didn't. Dutch regarded Uncle as a traitor after finding out that he along with Pearson and Mary-Beth left the gang.