The Million-Dollar Question: Was Dutch a good man with poor judgement who let the stress of his position, the loss of his dreams, and Toxic Friend Influence from The Molecorrupt him, or was he always a narcissisticsociopath throwing a tantrum because he can't have his cake and eat it too? Did he ever believe in his ideals, or was he just trying to justify himself to the gang? Did he see his fellow gang members as family, or was he just collecting a loyal cult around himself for ego-stroking and disposable muscle? John believes that it's the latter, while members like Sadie and Charles think that it's the former. Arthur, on the other hand, explicitly states he doesn't know, even after Dutch left him for dead.
Does Dutch actually love anyone? On the positive side, he's supportive to the gang until the Sanity Slippage kicks in, has had Susan and Molly as lovers, flirts with Mary-Beth, and speaks fondly about Annabelle, his former lover who the O'Driscolls killed. On the negative side, he's shown to be quite manipulative (and occasionally gaslights his subordinates) and his supposed care for his subordinates could be Dutch acting the part to get them where he wants them (for example, playing up how upset he is about Annabelle's murder to encourage the gangs' feud), and Abigail at one point bluntly tells Molly that Dutch doesn't really love her. The Blind Seer can tell John to stop seeking "the memory of those who pretend to [love you]," which presumably means Dutch.
Did Dutch really want to get back at Angelo Bronte for the set up and for stealing Jack, to clear the way to make money, or something deeper? His voice actorsuspects that Dutch harbored a particular hatred for Bronte because Bronte was essentially the corruption of Dutch's desires: Dutch wants to be a rich and respected crimelord surrounded by his loyal gang, but he's disgusted by Bronte. Even going with that idea, does Dutch revile Bronte because of some internal revelation that his own dreams are somehow faulty, or because Bronte did what he hasn't been able to do?
Did Dutch truly want to help Rains Fall's tribe, believing it to be a mutually beneficial relationship, or did he just want to use them as cannon fodder so that he could rob Cornwall one last time? Dutch not giving a damn about the Native casualties and refusing to cover their escape seems to point toward the latter interpretation. But there's also hints that his mental state had gotten so bad that he couldn't even realize the danger he put the tribe in.
When Dutch shoots Micah in the epilogue, is it because he is deeply regretful of Arthur's death and kills Micah in revenge regardless of whether he's a rat or not, or is it because he now truly believes Micah to be a rat and kills him to correct the mistake years ago? Did he realize that Micah is doing what he himself did to Rains Fall and Eagle Flies years ago, and stopped the man trying to manipulate his only remaining son? Dutch just wordlessly wandering off and leaving Marston to loot all his gold doesn't help the matter.
It's entirely possible that Dutch did indeed start off a good man with high ideals but in the years since the gang's first robbery in 1887 he was progressively worn down by the rise of civilization and the pursuit of the law until he finally snapped. The botched Blackwater heist, a possible concussion from the failed trolley station robbery, the death of Hosea, all of it contributed to the destruction of of his ideals in favor of simply lashing out at a world that continually (from his perspective) had it in for him.
How bad was Dutch's mental state after the Saint Denis bank heist and to what extent did that play in his more questionable decisions? Dutch can never quite explain his thoughts or plans. He seems as though he's in a daze at camp with a questionable grip on reality. Did Dutch mentally slip to such a extent that he couldn't even understand what he was doing? Were the later more violent and ruthless plans that involved abandoning Rains Fall's tribe to their death after setting them against the US Army the plans of an unhinged Dutch or Micah manipulating a mentally sick man?
Why did Dutch shoot Heidi McCourt? All that's said is that Micah was involved, she died "in a bad way," and the action was extremely uncharacteristic for Dutch. Did he genuinely think she'd be a threat to his gang, or was his ego prodded? Did he have a grudge against her for some reason? Did he genuinely screw up while trying to shoot something else and pretended it was intentional rather than admit he wasn't in control?
Was Arthur's choice to become a better person after his diagnosis with tuberculosis a case of a genuine Heel–Face Turn or was it more of a case of Villain's Dying Grace? The multiple alignment-based endings actually play on this, with his high-honor ending leaning towards the former and the low-honor one leaning towards the latter.
Likewise, his choices of if he decided to help random strangers, is it due to him being a Jerk with a Heart of Gold or Pragmatic Villainy? One example of this is the Stranger Mission, "No Good Deed", where he could help a colored doctor, whose medical wagon has been stolen. Did he help the doctor because it was the right thing to do, or because the fact that, due to being a wanted outlaw, with limited options for medical care, it might be a good idea to have a doctor who owed him a favor, in the likely event of injury or sickness?
Was Arthur angry with Micah for shooting up Strawberry out of horror that he murdered so many lawmen and civilians unnecessarily? Or was he just annoyed that Micah almost got the both of them killed?
How morally wrong was Arthur when he went to collect from Mr. Downes? Some fans see Downes as a good and terminally ill man still trying to work off his predatory loan. Arthur beating him senseless, greatly hastened his death and taking the rest of his family's fortune sent them into ruin. Other fans hate Mr. Downes for taking an "irresponsible" loan he couldn't pay back and infecting Arthur with tuberculosis. Also Arthur collecting the debt was "legal" and Downes would have died from his tuberculosis anyway, even without Arthur beating him up. So were Arthur's actions a callous Moral Event Horizon against an innocent man and his family, or was he just doing his duty providing for the gang?
How morally right was Arthur when he kicked Strauss out of the gang? Even as cruel as Strauss was, he was still a loyal member of the gang. For what it's worth, Strauss will leave the gang even without Arthur's intervention.
Micah
Was Micah always a traitorous rat planning to betray the gang, or did the gang’s impeding collapse as well as their mistreatment of him lead him to cut them loose? Throughout the story, Dutch is the only gang member consistently kind to him while Arthur and the others openly hold him in contempt.
Why did Micah turn rat to the gang? Was he promised amnesty and/or money? Did he hate the gang (Arthur in particular) for mocking and disrespecting him or for their repeated failures and general incompetence? Did the Pinkertons threaten someone he cared about? A mixture of the above?
Is Micah really racist, or is he faking prejudice in order to provoke minority members of the gang and amuse himself?
At Beaver Hallow, Micah attempts to take Jack out fishing. Was he planning to molest, drown or otherwise terrorise Jack, or was it a genuine attempt to comfort the poor boy?
Was Micah attempting to kill Arthur in their final fight, or was he holding back to further torment Arthur?
With the revelation that Micah was The Mole, it raises questions of his motivations and actions over the course of the game. While Milton said that Micah only became the mole after Guarma, a lot of his actions prior to that have already given the gang more than enough trouble. Did he intend to sell the gang out right from the start, or like Milton said only did so once it's clear that things were going downhill for the gang after the botched bank heist in Saint Denis?
Micah's surprised silence when Arthur tells him and Dutch that John "made it". Had Arthur struck a note with him and Micah felt moved that Arthur sacrificed himself for John? A sombre realisation that he will never get the chance to live a peaceful life with a happy family like John? A shock that John managed to get a life as a free man, like he wanted? Or just a horrified realisation that Arthur had finally gotten through to Dutch? Or maybe he realized that John disappearing left him with a dangerous loose end he couldn't easily find and remove?
Agent Milton
Is Agent Milton a decent man whose quest to hunt the Van Der Linde gang a fully justified crusade in light of their crimes? Or a Inspector Javert-esque hypocrite who causes more pain and misery for the common people than the Van der Linde gang does?
Did Milton offer clemency to the other gang members out of pity for their circumstances, or was it just an attempt to get them to give Dutch up? Would he even have kept his word?
Did Milton know young Jack Marston was in the shack in Lakay when he ordered it shot down?
Why did Milton tell Arthur that Micah was the rat? Was he planning to taunt him before killing him, or did he hate Micah so much that he wanted to have Micah Rewarded as a Traitor Deserves and send Arthur or Sadie against him if Arthur surrendered or somehow defeated him?
Was Milton even telling the truth when he said Micah was the rat? Or was he just trying to twist the knife into Arthur or turn him against the gang?
Sadie
Is Sadie a badass, wisecracking Action Girl whose actions are understandable and forgivable? Or a JerkassPsychopathic Womanchild lashing out and bringing more heat on the gang?
Does Sadie help Arthur and the Marstons due to growing to like them? Or had she realised that Dutch was bringing the gang to Hell and wanted allies to protect her?
Is Sadie's violent nature justifiable and restrained, or is she potentially as bad as Micah?
Is Sadie's violence purely due to her beloved husband's death and the abuse the O'Driscolls subjected her to? Or was she always a brutal and bloodthirsty woman with Jake being the only thing anchoring her to a civilian life?
Is Sadie truly reformed by the Epilogue? She mentions doing "good things and bad" in a conversation with John and proves quite cold and ruthless while hunting Micah. Does she possibly have any sidelines in criminal acticity?
Does Sadie shoot up Colm's execution due at an enraged outburst? Or was it a suicide attempt and/or an attempt to get Dutch killed so he won't endanger Arthur or the Marstons? It's might be worth noting that Dutch stops bringing Sadie on missions after a while and only does so when the whole gang is there to back her or him up, as though he knows that she either has it out for him or is suicidally reckless.
Does Sadie execute Cleet out of hatred for him and his association with Micah, to prevent him from warning Micah or the authorities, to collect on his bounty later or to prevent him from taking revenge on her, Charles and/or John in the future?
On her shopping trip with Arthur, was Sadie telling a bad joke or was she serious about killing the shopkeeper and robbing the store? If she was serious, was it because she assumed that this was something the gang always does, or was she already itching for a reason to violently murder someone?
Why didn't Sadie (and Charles) help John in the original game? Did they not know that he was being blackmailed by the FBI? Did they callously abandon him? Or were they already arrested or killed, possibly by the FBI?
Others
Javier and Bill choosing to stay with Dutch even as the rest of the gang members left. Was it out of Undying Loyalty, or was it because both of them were afraid of being left without a purpose by abandoning the man who saved them at their lowest point?
Speaking of Javier, his lack of a Love Interest and fondness of Marston in both games (to the point of yelling, "I've always loved you... even now!" when John chases after him in 1) could be seen as a one-sided crush on John.
It's surprisingly easy to interpret Bill as a Woobie, Destroyer of Worlds. A Shell-Shocked Veteran who has ended up with a Cult led by a man with Delusions of Eloquence. He's also potentially a bisexual or gay man in a time when that is enough to get you killed, with many of his gang members, even the sympathetic ones, holding period-accurate attitudes towards it. By the end of the gang, he's found all of his Found Family dead or turned on one another.
The are some subtle hints that John may actually be afraid of (deep) water, such as his breathing slightly intensifying near deep water in the epilogue. If he is afraid of it, is it because he can't swim, or did he never learn to swim because he's afraid of water? The latter could imply some sort of water-related Freudian Excuse.
Did Colm really not care for his brother, or did he still love him despite their disagreements and sought revenge on Dutch, telling Dutch he didn't care about him to mask his feelings?
Tilly Jackson's past with Anthony Foreman's gang, and how she ended up killing his cousin, is never really explained. Grimshaw states that she killed him for good reason, but this doesn't mean much since Grimshaw makes it clear later on that she doesn't care what the reason was. Tilly is also noticeably cold and ruthless at times, best shown when she callously justifies Molly's murder for apparently betraying the gang (she didn't, which Karen and Mary-Beth suggest early on), so while it's still possible that Anthony's cousin had it coming, it's equally likely that Tilly wasn't so innocent in the situation.
Is Hosea a benevolent and competent leader, or the same breed of arrogant, self-righteous criminal as Dutch is, just one better at masking his intentions? He and Dutch recruited many of their gang members as children or from the helpless and impressionable and raised them to be criminals. All of his big schemes fail: his attempt plan to pit the Grays and Braithwaites against each other leads to Sean's death and Jack's kidnapping and his insistence that they rob the Saint Denis bank after killing Bronte led to his own and Lenny's deaths and started the downfall of the gang.
Is Strauss a cold-hearted loan shark? Or is he just trying to keep the gang afloat, and is really no worse than the other gang members?
Did Strauss not sell out the gang out of loyalty like John believed, a Heel Realization that Arthur was right about him and he deserved to die, or was he more afraid of the gang because they spent the majority of the story killing loads of government agents, knowing that they’d come for him if he ever spilled the beans?
Does Mary genuinely care for Arthur or is she just using his affection for her to get what she wants? Or is she just a woman in a bad situation in a time in which society didn’t give women in bad situations a means to get out of them by themselves so has to call on the only man she can rely on to help her? Is it a little bit of all that?
Did the old woman, Gloria, really intend to betray Dutch and Arthur if she wasn't paid or was it just Dutch rationalizing? She's already been paid a gold bar (an absurd amount of money about $30,000 dollars equivalent at the least) for leading them through a cave and draws a knife on them when Dutch refuses to cough anything up. On the other hand, she was utterly helpless once Dutch grew sick of her demands and Dutch could have easily thrown her aside. She also only pulled out her knife when Dutch menacingly gripped her, likely sensing that he was about to turn violent.
Chapter 6 retroactively gives alternate viewpoints for Ross's motivations in I; Once Milton dies and Ross takes over his job, only 9 members of the gang remain at Beaver Hollow - Dutch, Susan, Arthur, John, Micah, Bill, Javier and Micah's buddies, Cleet and Joe. Susan is shot as the Pinkertons arrive at the scene, Arthur dies shortly after, and Micah, Joe and Cleet are all killed in 1907. This leaves only Dutch, John, Bill and Javier - the four people Ross was adamant about taking down in 1911, while here there are many more surviving members Ross had met at least once yet ignored. Were his actions a genuine attempt to brighten the world, and he left the others alone because they had changed, because their deaths wouldn't bring Ross fame and/or were Not Worth Killing? Or did he go after the four just to satisfy a petty vendetta born after he failed to catch them all the way back in 1899? Or was he focusing on the four out of respect towards his former colleague, in an attempt to bring his (apparent) killers to justice? Sure, in any case he's still a Glory Hound who milks his role in the events for all its worth, but it does rise the question of how personally he was invested in bringing down these four specific people.
Was Kieran really kidnapped by the O'Driscolls, or did he betray the Van der Linde Gang and return to them voluntarily and was subsequently Rewarded As A Traitor Deserved?
Did Thomas Downes cough onto Arthur by accident, but was he deliberately infecting Arthur with his tuberculosis? While he is a Nice Guy, Arthur beating the daylights out of him may have soured his disposition on him. What's one less murdering outlaw to the world?
If Milton was lying that Micah was the rat, was there no rat, or was there someone else?
Trelawny is the first member to abandon the gang. As a mere associate of the gang who rarely stayed with them, he spends plenty of time away from the camp doing God knows what and meeting with God knows who. Arthur had expressed his distrust and contempt of him in the early chapters. Trelawny also shows slight classism and elitism towards the gang as degenerates sleeping in the dirt and likely.
Also, unlike the rest of the gang, Trelawny has a family separate from the gang. It's possible that the Pinkertons learned about Trelawny's connection to the gang, and threatened his family so he would sell the gang out. Milton and Ross only find the Clemens Point camp after Trelawny arrives.
Reverend Swanson is second to abandon the gang. While the rest of the camp fall to paranoia, alcoholism or infighting as it collapses, Swanson surprisingly recovers from his vices. And as the most moral person in the gang, he may secretly disapprove of the violent criminals he lives with and wanted to atone for his and their sins by ratting them out.
As stated above, Tilly's departure from the Foreman brothers may not be as black and white as she tells it. Unlike the other girls, she is insistent that Molly is the traitor and is uncharacteristically cold about her death. She also manages to hide away with Jack from the Pinkertons while Abigail is captured in the final missions.
Mary-Beth was first found by the gang running away from a group of men she pickpocketed, already proving that she's more than a sweet innocent flower. She was the one who tipped the gang on the train robbery in Scarlett Meadows which got quickly ambushed by lawmen. Tellingly, she, Karen and Jack are the only ones absent when the Lakay hideout is attacked by Pinkertons. She also leaves the gang right before the final mission when the Pinkertons raid it.
Charles is the most moral and compassionate of the gunslingers and knows that the gang are nothing but criminals, so he may have turned rat to atone for his crimes. Dutch's backhanded dealings with the Indians only proved that he didn't care about his people. In addition, despite exposing himself to Pinkerton agents after the Lemoyne bank robbery, Charles manages to escape the heavily guarded streets on foot despite instead of being arrested or shot and has a flimsy story of hitching a ride away.
It's also possible that the rat was numerous people within the gang too, at various points during the game for their own reasons.
suspects that Dutch harbored a particular hatred for Bronte because Bronte was essentially the corruption of Dutch's desires: Dutch wants to be a rich and respected crimelord surrounded by his loyal gang, but he's disgusted by Bronte. Even going with that idea, does Dutch revile Bronte because of some internal revelation that his own dreams are somehow faulty, or because Bronte did what he hasn't been able to do?