Agent Milton - A Killer Behind A Badge 

Just wanted to talk about Milton today I guess…

I can’t lie, “you people venerate savagery and you will DIE, savagely” is a hard ass quote

Killing Hosea was an attempt to bring Dutch down back to earth. Instead it only made him spiral further

He was too soft with The Van Der Linde gang he could have killed them all in chapter 3

I mean milton is honestly the most reasonable guy in the game The moment he walked inside the camp he didn't show hostility or anything bad Or when he saw Arthur fishing He literally could've shot him and kidnapped jack sure that would be savagely but sure could be a impact on the gang Or that Mac calendar I mean he could have lied about him and didn't say he did it All I'm saying Is he is pretty realistic and honest Sure we hate him because we have to fight him....but we are criminals with alot of blood on our hands

Milton at first gave the gang chance after chance to just give up Dutch and leave, but from the bank job to his death he seemed more and more sadistic and evil. I imagine he spiraled down as the story went on a bit like Dutch did, due to growing pressure from Cornwall and the gang continuing to escape him. We just didn't see as much of it because it was off screen.

Ross saw what happened to Milton when he showed a little reason, and that led to him being more sadistic, to the point of killing the man he promised freedom for him and his family.

I love Milton as an antagonist in the game, because he's a great foil to Dutch. Dutch presents himself as a messiah and the figurehead of an idea, the idea of freedom, loyalty and the "noble outlaw" life. When Dutch takes drastic measures he justifies it as being necessary for a greater cause. Over the course of the game, we see Dutch's facade unravel and degrade to a raw fight for survival, where he's shows he's willing to just use and then throw away his friends and allies, leaving them behind, if it means he gets to keep living. All this belies the words he spoke at Davy's funeral in the first chapter. Part of what makes Dutch seem delusional and irrational late in the game, is because Dutch can't accept his own hypocrisy. He goes mad trying to continue to see himself as the noble outlaw hero, even as his actions abandon the principles he claimed to represent and taught to his followers. He starts casting everyone else, even his best friends, as the villains for being against him, because Dutch will never accept that he could be anything but the noble hero, no matter how far he goes. Milton similarly presents himself as the representative of a greater cause and a supreme ideal. For Milton it's the Law and American Civilization. He claims to be a righteous representative of a noble government and therefore everything he does, no matter how despicable, must be heroic, for he is more than just a man. In order to maintain this heroic view of himself, he dehumanizes and degrades the outlaws, because "killing or torturing people is wrong" but "Killing or torturing filthy outlaws is justice, and necessary for the progress of civilization in the west." Just like Dutch's facade of the "noble outlaw" degrades throughout the game, Milton's facade as a righteous agent of justice also degrades and unravels. He hates Dutch and also Arthur because their nobility and loyalty to their people undermines the identity and philosophy Milton uses to paint himself as the hero. And there continued resistance forces him to take measures that contradict his constructed image of himself. Early in the game Milton's offers of deals, and gives speeches of supposed "mercy." His language and sentiments are pretty similar to Dutch's many speeches about how he's gladly die for his people (in Milton's for his country) and that he is going to lead all who listen to him into a better world. Milton makes those offers because he's acting the hero and it's what the hero does. But just like Dutch never really had the principles and courage to lay down his life for his friends, Milton never was righteous nor civilized and only ever wanted to dominate and crush the spirits of those that opposed him and his idea of how the world should be.

I was disappointed Milton didn't get more screentime. He was a easily a much better antagonist than Micah. And while he wasn't perfect, he was certainly justified in hunting down what was essentialy a terrorrist, mass murderous cult. It could be argued that Milton was a necessary evil.

I don't hate Milton. I also don't think he is "evil" as many people always say. He has given the gang plenty and plenty of chances to run away if they'd just abandon Dutch, that silver tongued liar as he likes to call him. Initially he only wanted Dutch and I truly do believe he'd have spared everybody else if Dutch turned himself in, or if the gang handed him over. Let's not forget this one thing....the gang is a bunch of criminals and killers. It's difficult to remember that sometimes because we play as them and grow a liking towards our little family, but that doesn't change the fact they are murdering thieves and criminals. Some worse than others, but still. Milton grew very impatient when Dutch/the gang continued to rob and murder, and only that's when he kinda snapped and shot Hosea in cold blood. I think it was to send a message, that he really means business and that all of them *will* die because of Dutches actions.

I don't hate Milton. He's doing his job. He did it pretty honorably compared to Agent Ross in RDR1. Agent Ross I hate, he's a scumbag. Milton though is just a young, ambitious pinkerton that wanted to rise in his career. I didn't really like how he took his job so personally though. Like he was personally insulted by Dutch and his boys.

The scene where Milton talks to the gang at Clemens Point is pretty thematically on point for another reason. John calls himself Rip Van Winkle, a character from a short story by Washington Irving about a Dutch-American man who falls asleep in colonial America and wakes up after the war for independence. For a game all about how time is passing the outlaw gangs by, it’s a pretty potent allusion, and one that is kind of surprising for John to know enough about to joke.

I’ve never hated Milton. I just saw him as a man doing his job.

Milton really could have lied and just sent lawmen right after the conversation but he chose to warn them he didn’t have to do that he could’ve went in guns blazing like Ross did I honestly think he would’ve let John go had he lived Ross betrayed John also when Milton says they killed those “savages” he was talking about the indians

I think that it's important to clarify that Milton is not a "lawman." Though, the Pinkerton badge gives the impression of being a government official (and several governments contracted their services). At the time of this story, the Pinkertons were a private security agency hired by Cornwall for the primary reason of protecting his trains and railways. Milton mentioned the territorial and federal governments because railways weren't federalized back then. Governments contracted with railroad magnates (like Cornwall) to ship mail, people, and goods across the country. To be in the service of Cornwall is also to be in the service of the governments that are under contract with Cornwall. By attacking Cornwall's trains, the gang is both directly and indirectly attacking the territorial and federal governments. This is why it is important for Milton to appear to act within the confines of the law. Had Milton been able to capture Dutch, he likely would have escorted him to a W. Elizabeth jail. After which, (considering the bounties) the Pinkerton Agency could have potentially collected payment from Cornwall, West Elizabeth, and maybe even good old Uncle Sam.

When you think about it, Milton played it fairly straight. He as a "lawman for hire" gave them the warnings and then resorted to brute force, all by the book. Ross' approach was way more subtle and twisted, taking a whole family hostage and making John doing his dirty work.

Still better than Ross, though lol. Wish we would've gotten more interactions with him. The voice actor really nailed the role!

Milton was a sadist, he loved to torture and torment his targets On the other hand, Ross was brutal, he played dirty to complete his objective. He probably took such approach after he saw what happened to Milton

Andrew Milton was a very patient man. He was only doing his job and he did it good within the confines of the law; he never once actually killed any members of the gang unless there was an actual crime being committed. (unlike Ross) Milton’s problem was that he hesitated too much, and it cost the lives of many of his colleagues and friends. He stopped hesitating and killed Hosea as a message to Dutch, and became much more persistent and aggressive. Despite his need to change, he never had the heart to actually outright kill someone unless he felt they truly deserved it. He believed that the members of the van der linde gang were being manipulated by Dutch, and he wanted to give them chances to leave while they still could. In the end he lost his life because he hesitated. Despite knowing that Arthur was the most dangerous man in the country that could kill him faster than he could blink, he still never actually viewed him as a genuine bad person. Just a man following the wrong star. He knew that Arthur was a good person because he’d met people that Arthur helped. Milton was a good guy following the rules in a world where the rules don’t work anymore, and people will find their ways around the rules for their own personal goals and needs. Milton was different.

I actually like Milton he is one of the more honest pinkertons he tried to give the gang chances to give up Dutch or disband

“5000$ for me? Can I turn myself in?”-arthur Morgan 1899

I don't understand gamers bashing character they dont have proper background about just because this character was an obstacle for main protagonist. He could have killed Marston and Abigail and Sadie! But he didn't. He even offered deals to group to surrender Dutch. This guy ran out of patience with dutch. robbing hard earned money 9f saint Denis people that why he killed hosea! God knows how much chaos Micah and other gang members caused that was not shown. Most of them were savages in thr gang except for a few who had some morales.

I forget his name, but there’s a retired mob guy on RU-vid that was talking about how a lot of FBI surveillance people would make themselves known. “Hi, I’m Agent Johnson, this is Agent Marco, and we’ve been assigned to follow you. We’ll be right over here if you want to get out of the life.” And they’d do it any time they got assigned to a new target. Not everybody wants to go out in a hailstorm of bullets. I can only assume that this is exactly what Milton and Ross are doing in this game.

Milton was reasonable while Ross was evil.

I always think that Milton kind of reflects Dutch in the fact that they both spiral out of control by the end of the game with Milton being reasonable in the beginning as he just wanted Dutch but by Lagras he goes insane wanting to kill the whole gang including the women and Jack

Even if Arthur took his offer of ratting Dutch out, Milton would just go "Oh I promised you wouldn't swing, never said anything about you not rotting in prison for life."

He actually seemed pretty alright behind it all. He gave the gang lots of chances. He could have just brutalized the camp in chapter 3 but he didnt. He could have took in arthur and jack in chapter 2. He wanted to cut off the snakes head.

One thing to keep in mind about Milton's brutality as well; The more brutal he got was a direct response to the gang's increased violence. The more the gang robbed not just banks, but regular people, destroying property, killing dozens of people who aren't just other outlaws, the more Milton gets vicious. And even the its not until the gang kills ALOT more people that Milton stops offering deals and starts wanting all of them either dead or arrested, the women included (keep in mind, Sadie and Karen have been seen directly robbing and killing, and all of the girls work to help the gang.) Alot of people forget that the gang we play with are the bad guys, they kill innocent people and rob the little guy for themselves and act like they are better than other gangs doing the exact same thing.

I think a big reason for Milton not using a maxim gun at saint denis is civilian casualties. Being in that it is in a big city and there are hostages with no affiliation with the gang in the bank.

And to think that in the end, milton got what he wanted. With agent ross carriying on his mission in the red dead sequel and you (the player) as john marston killing of the remainders of the van der linde gang. If only at the time I played the first game I knew that I was doing Milton's left over dirty work

Yeah there’s absolutely NO WAY he didn’t know who John was. And if he really didn’t know who John was, there’s no way he would let the gang know that unless it was for some strategy

The only members of the gang that Milton knew were Dutch, Hosea, and Arthur. He them because they were the main members of the gang. They were in the gang for 20 years. And also in the missing where we rescue Sean Javier says that were pictures of Dutch and Hosea in Blackwater

I would love to see an in depth video of why Dutch decided not to leave after all. At the end of the game if you choose to go back for the money, there was $40,000. That should have been more than enough for the gang to start over and then some.

The thumbnail really goes both ways, saying The Imperfect lawman or The I'm perfect lawman.

12:56 Pinkertons were basically Mercs for hire and did a lot of work with the US Government, but they accepted work from anyone who could pay for it. This scene is the first time Pinkertons are working with more than just federal funding, which can get you 2 agents. Cornwall had to have unloaded barrels upon barrels of gold in order to cover the cost of all that artillery

Milton wasn’t just a lawman, he was a man playing a game. He loved the chase, he would play mind games and see if the gang implodes.

Another noteable thing is that he didn’t cause Molly’s death. She pretty much committed suicide, yes and questioned her to the point of her breaking down but they stopped after knowing they couldn’t get anything from them. Not saying what they did was right but Milton was throughout the game pretty consistent when it came to showing that he didn’t enjoy causing mass pain to the gain only did things that were considered needed.

I'm pretty sure nobody considered Hosea's death a murder. There's no telling how many people died in the explosion he set off

Agent Milton was a huge jerk, so much so that even his own men hated him, but at the same time, we do see him try to give the gang as many chances as he could. He even admitted that he didn't want to slaughter the whole gang, he merely wanted Dutch, and despite the others being criminals, he gave them the opportunity to leave in peace. It was only after the gang persisted, that Milton went no-hold-bard on them. So really, Milton wasn't the man at fault, not really. The real problem was Dutch.

Love the video. I've liked the theory ones too. Have you ever thought about making a video about the different members of the gang getting tuberculosis instead of Arthur and how that would have changed things, just a thought.

See I liked Milton because he actually cared about his job. Ross is just corrupt to the core and not only that he has no morals as to where Milton has a clear moral standpoint

I think Milton early on was not saying anyone would get a pardon, but he was specifically there for Dutch. Without Dutch there is no gang, and if they betrayed Dutch he would more of just ignore them when they ran away and not track them down. There was no point in it. Now, that's something that can't be said for Ross. Ross was nearly identical to Dutch but on the "right" side of the law, he lied to and manipulated John just to betray and kill him. I think Milton likely would have just let John go after he did his job. What I like about my theory is that in RdR1, Milton is the head agent and somewhat decent, while Ross is no better than the men they hunt. But in RdR1, Ross is the head agent and no better than the criminals, while his second (can't remember his name) seems like a genuinely decent person just trying to do right, and is even respectful to John. (Note that in both games, Ross isn't there in the end for Milton, and Ross' second isn't there when he kills John, or when Jack goes to kill Ross.) I like how it all plays out.

Ross lead the charge at the end of chapter 6. Milton would've taken some of them alive, Ross went in guns ablazing

Milton was lucky Aurther didnt smoke his ass.

Dutch as well as most of the people in the gang are evil and Milton had every reason to be cruel to them but chose to give them multiple chances to turn Dutch in and live normal lives.

I find it somewhat funny how Milton threatens the whole game with fifty men. Arthur alone can take at least thirty, Arthur and John can probably take all fifty.

Pretty sure Dutch shot that black girl in blackwater the same way Milton shot Hosea. Milton probably saw that and realized just how seriously he should be taking Dutch. More importantly he realized the squad follows Dutch.

Has anyone noticed that Milton (Agent, not Jim) looks like Gary from Bully. Gary was the main villain in Bully. We know that Jim boy calloway is Jimmy, the main character from Bully so maybe Milton could be based off of Gary, the villain. I know this is a stretch but it's good food for thought.

Some people here don't seem to understand. Milton didn't give Dutch and the gang "chances". He would have seen them all hanged. He just wanted Dutch the most because Dutch kept finding a way out of his grasp. He wanted to kill Dutch in such a way that made him feel powerful, not in a shootout like Mac ... which he probably lied about killing (Mac was most likely dead already). Both Milton and Dutch want control. Milton tries to gain control by extortion and fear. Dutch gains control by contempt for authority. Neither men are really "evil" but both are willing to kill in order to get what they want. Neither of them are capable of admitting wrong or seeing the world outside of their black and white mindset, despite both men acting contrary to the beliefs they claim to uphold.

Great video real in depth

12:50 they did bring in a maxim gun during the robbery,it comes out on a wagon once Arthur gets on the roof

Been waiting for a video on Milton forever. I agree with you. He’s just a reflection of Dutch. It’s pathetic that he thinks he’s worth something, isn’t it?

One more very nice video on RDR story and characters personality traits. 👍

Milton is very right about dutch. Completely looking through dutchs bla bla and seeing the killer he is. While dutch was trying to be more, he certainly didn't end up like that

i think its interesting that even his own agents hate him. he does seem arrogant like you said, and he underestimates his enemies.

His "badge" is a trinket, he's employed by a private company and has no government-delegated authority. This means, that he had no authority to let people go or to negotiate softer punishment for Arthur. He was lying to Arthur and the whole gang, and they knew it. Juridically he has no difference with van der Linde. That's another gem in the crown of the RDR2 storyline.

Rdr2 is filled with so much great content

Something to note about your comparison of stand-off in Saint Denis and assault in Lakay - Saint Denis actually had a genuine risk of innocent people being harmed in the crossfire, as gang had hostages within the vault. Dutch even mentions that if Milton tries something stupid, he's going to harm said hostages. My guess is that Milton legally couldn't bring Maxim machinegun and the likes with him, as it's power would've been a genuine risk for the hostages. On the Lakay, there was no hostage situation - the gang, albeit containing non-combatants, didn't had any leverage. Milton could've went all out.

Milton might be one of the most honourable characters in the game. That being said, the only thing I dislike about RDR2 is that we didn't get to shoot this MF ourselves.

John could of walked away right then and there and he would of been know as rip van winkle!

Maybe he mentioned Cornwall first at Lakay because the government stopped supporting him for whatever reason but by that point he was just desperate to take the gang down for good

At the Lake encounter I like to think at that point Milton felt insulted that Dutch was still alive seeing he when he got Micah he thought Dutch died at sea, but learning he was still alive he might have felt it was a insult to him personally that this one man that kept evading him is still out there alive

While you’re waiting on top of the bank for them to come a maxim gun shows up during the bank robbery

They should have given him some badass action scene, something to prove he is a real danger for the gang. Kind of like Stephen Lang's character in the movie Public Enemies against John Dillinger

Bruh I just thought. What if Milton was boning Heidi?

Milton was an excellent Antagonist any game would be lucky to have. R* did an incredible job as always.

The one thing I hate, hosaya looked at his killer, the only person other than him to do the same is Arthur, (micha) never look your killer in the eye

nobody would have been spared. Miltons offer would be similar to the one Ross gave John. To quote Dutch "when Im gone, the will find another monster"

6:13 - I'm reminded of the phrase from The Suffering: "Blame the Sin; not the sinner." I wouldn't doubt Agent Milton views Dutch as the embodiment of the romanization of an Outlaw, and how that MUST be punished for civilized life to thrive.

I think milton was a outlaw with the way he knows how Dutch thinks so well. Takes a criminal to find one an all. Plus he has some degree of honor, he could have shot Hosea in the back but waits till he turns around to shoot him in the chest. I think in his eyes he has to be evil and violent so noone else has to deal with it, like some jind of martyrdom

A game from the perspective of law enforcement, including the time Landon Ricketts was a policeman at the Blackwater Massacre would really bring the full circle, much like Jack at the river twice.

Edgar Ross would later become the main villain in the first game

Fans hating on Micah cause he ratted out the gang, antagonizing the gang, killed Jack's dog and taunting him for it, teasing Arthur's declining health Most Fans hate on Micah for the sake of hating him Once I read a comment from a video about Micah saying "I hated Micah as soon as he appeared on screen" Lmao ook talk about being dramatic 😂 Agent Milton I've also seen comments saying that he was just doing his job technically yes but his way of dealing with them is quite questionable Sure he made a bargain with Arthur and Dutch but after they didn't budge I understand his frustration Yes he could've taken that moment in Saint Denis to bring down the gang mainly the men with a full army And he actually did But with plot armor and good shooting from Arthur they survived well some of them In Lakay I do agree Milton was fully aware that there was women and a child with the gang and he just straight up fired the hell out of em with no hesitation Honestly the gang had it coming to them They're days of robbing and killing with no consequences were over and most of them were in denial that things would be OK for them and they'll get out Milton probably enjoyed the thrill of shooting at the gang

Arthur said no to the Pinkerton's. John in RDR1 said yes. Look how that turned out for John.

From Milton's perspective it wasn't that he was willing to kill Jack more like he thought it was irresponsible having a child around a bunch of killers. He could even convince himself it was for Jack's safety to get rid of the gang the way he did

Milton must’ve been those kids in school that reminds the teacher they have homework

I feel like the pinkertons were really just on the ‘legal’ side of killing. He acted as much of a crook as anyone in the gang did. Pinkertons were private security/detectives so they generally went unsupervised I feel. ESPECIALLY in the Wild West. Awesome video!! Milton is a fav of mine.

Milton is a great antagonist, Ross is a villain. Milton is the bad guy because he's just doing he's job. Ross is just a horrible person.

Someone needs to make a mod to make milton look like adam schiff with his evil bug eyes

RS should make a game where you play as Milton, starting as a young man, up until his death.

I feel like the reason they were soft on the gang was bc they wanted to pic them off one by one by firstly getting rid o thief leader

Do you think it's possible Milton underwent a change in Chapter 3 after the bloodbaths in Rhodes and after the trolley station robbery in chapter 4? He may have felt all those deaths were on his shoulders, hence why he didn't even negotiate at the bank

He still had a lot more honour and gave the gang way more chances than someone like Edgar Ross

Don’t forget that when they said “dead or alive”…they meant it. This wasn’t a time of Miranda rights and concerns about police brutality.

Nah. Ross is worse than Milton

the simple fact is milton gave the gang numerous chances, realistically he could have wiped out the gang all the way back in chapter 3 on a multitude of times milton continuously stated that he only wanted dutch allowing the gang to run free and live new lives

Question for anyone who reads this , would Milton had honored a deal with John Marston with getting his old gang members in RDR 1 if had been him to do it instead of Ross or would Milton end up double crossing him all the same ? 🤔

Even Kieran drew his gun on Milton at Clemens Point

,,My Name is Dutch Van Der Linde, from the Van der Linde Detective agency! I have a warrant for You and your Band of Outlaws Mr Milton!"

Could you imagine if Rockstar made Milton the brother if the women Dutch killed during the blackwater massacre? It'd add some serious motivation to his character, and might add some truth to, "I only want Dutch."

I want a DLC where you play as Milton and hunt down the Van der Linde gang from his prospective

“Rip van winkle-John 1899

When fishing, Arthur should have heard them come up right behind him on horses, let alone Jack would see them behind Arthur. Just frustrated me at that point.

Milton clearly only cared about theor leader dutch clearly stated in the chapter 3 ending, same with the saint denis bank robbery where he is addressing dutch rather than the gang I think its because he saw that the gang included women and children when he encountered arthur and jack , he only wanted dutch and kept finding excuses to not aprehend them by the time we get to chapter 6 he is gunning for all the gang mainly the man power his last warning and the begining of his hunt in the fleeting joys Mission

That is absolutely not when the Pinkerton's started in on Dutch's boys, they were already onto them at the time of the blackwater heist

This game is about the death of rockstar games. And Arthur dying is representative of Dan Houser being forced out of the company he started with his older brother Sam Houser

I like reading the comments as much as I like watching the videos.

I like Milton he gave the gang so many chances just wanted dutch but agent Ross i hate because john did so much for him and only wanted forgiveness but Ross shot him anyways

People are overlooking the fact that Milton may have had the same plan as Edgar Ross in RD1, but if his plan have worked and they went their separate ways and like with John they let their guard down soaking the piece and then the b@$+rd comes with his 50 man and shoots them all dead along with their family, remember this all started with the black water feiry job, and we all know that it was definitely a setup, in Milton did not hesitate to tell Arthur what happened to Mac Calendar in front of young Jack, dude is no different than the outlaws he hunts, willing to kill in any way possible for money.

What is that music in the background starts at 05:50 been looking for it like crazy