Larry Milton

"You fools weren't listenin' to me, were you?! I showed mercy... And you mistook it for weakness! Now I will show strength and you may mistake it for brutality! There is NO ESCAPE for any of you! I shall haunt you to the ends of the Earth and the end of time. I've killed your friends, and I enjoyed killing them and now I'm gonna kill each and every one of you!"

- Larry Milton taunting Dutch's Gang before his men start shooting at them

Leland "Larry" Milton is a major character and the secondary antagonist of Red Dead Redemption 2. He is the Director of the Pinkerton Detective Agency and the boss of Edgar Rose.

Biography
Milton is a detective and the leader of the Pinkerton Detective Agency. After Dutch van der Linde robs his train, Leviticus Cornwall hires Milton and his homeboy, Edgar Rose, to track down Dutch's Gang and eventually bring Dutch down. He gets some help on the side from Gicov Bell and Leopold Strauss.

Interactions
While Dutch van der Linde and his bearded, bathless bunch rest their ss at Horseshoe Overlook, Arthur Morgan and Jack Marston go out fishing. Milton and Edgar Rose approach them to surrender and turn Dutch in, in exchange for full immunity for him and most of the other gang members. When Arthur refuses, Milton reveals that they captured Mac Calendar and killed him slowly, enraging Arthur. After smothering Morgan up with some pro-capital philosophy, Milton and Rose leave.

Milton and Rose then approached Dutch himself and his gang at their new camp in Clemens' Point. He offers Dutch a chance to surrender in exchange for a new start for the other gang members and for them to leave. Dutch pretends to comply, but the gang members all draw their weapons. Flustered, Milton warns Dutch that he will be back with fifty men next time and that the gang should leave quickly, expect van der Linde, who he desperately needs.

While Dutch's gang is robbing the Saint Dennis bank, Milton captures Hosea Matthews and holds him hostage outside the National Bank, which Larry had surrounded with his many men. Milton states that any reservations for making deals have been exhausted and long dead, and subsequently shoots Hosea in the chest, killing him. A gunfight ensues and Dutch's gang manages to escape.

After the gang returns to America from Guarma, Milton and his agents pick up Gicov Bell who with utmost pleasure became their informant, like Leopold Strauss did months ago. With that, later Milton attacks the gang's hideout in Lakay, ordering the cabin the gang was holed up in to be riddled by a Maxim gun and his 50 men as he promised earlier. Despite his best efforts, the gang manages to repel the attack.

Quotes
"What a fine young man! But in a such complex circumstances... Arthur, isn't it? Arthur Morgan. Yes... Arthur Morgen. Van der Linde's most trusted associate. You've read the files; Typical case, orphaned street kid seduced by that maniac's silver tongue... and matures into a degenerate murderer. *Points at himself* Agent Milton. *Points at his boi, Edgar Rose* Agent Rose. Pinkerton Detective Agency: seconded to the United States Government. Nice to finally meet. We know a lot about you."

- Larry Milton introduces himself and Rose to Morgan and also tells some of his backstory

"Listen... This is my offer, Mr. Morgan; Bring in Van der Linde, and you have my word you won't swing."

- Larry's offer to Morgan

"I enjoy society, flaws and all! You people venerate savagery, and YOU WILL DIE! Savagely! All of you."

- Milton to Arthur

"Not a problem, but visitors... A solution. Good day, fine people. Mr. Van der Linde, Mr. Matthews, I presume. And... who are you??"

- Milton when walking into Dutch's camp, asks about Marston and after being called a problem

"I don't know if you're aware but this... is a civilised land now. We didn't kill all 'em savages only to allow the likes of you to act like human dignity and basic decency was outmoded or not yet invented. This thing? It's done. Who made you the messiah to all these souls you've let so horribly astray? You ain't much of anything more than a killer, Mr. Van der Linde."

- Milton to Dutch and about the past

"You'll be dead? Sure... But I? I'm gonna be just fine. We offered you a deal, Mr. Morgin, you should've have taken it. Not all you boys have quite so many scruples. Old Gicov Bell? Molly O'Shea? We sweated and canned her a couple of times, didn't say a word, had to let her go. But o' Gicov Bell? We picked his s up when you boys came back from the Caribbean. He's been a good boy ever since. And Strauss? Strauss has been with us ever since that failed robbery in Gold Town."

- Milton reveals who the two traitors of Dutch's gang were and that Morgan should've have taken the deal

Death
"You're losing your strength, Mr. Morgan..."

- Larry's last words Milton later captures Abigail Marston and holds her hostage at the Van Horn Dock, prompting Arthur and Sadie Adler to rescue her with everything they've got. However, Sadie also gets captured by Milton and almost raped, and Arthur is forced to confront Milton himself. Milton sneaks up behind Arthur and holds him at gunpoint as he tries to un-hogtie Marston. Larry then finally reveals that Gicov was the rat all along, having started talking after they picked him up shorty after the gang came back from Guarma and that Strauss had been selling them information ever since that botched ferry robbery in Gold Town at the start of the game. Arthur grabs Milton's gun, but is unable to overpower him due to his illness, TB. Fortunately for him and pretty sad for me, Abigail manages to break free of her confinements with a knife and proceeds to shoot Milton in the head with a revolver before he can execute Arthur. Despite his death, the Pinkertons, now led by Edgar Rose, continue their hunt for the remainder of Dutch's gang.

Personality and traits
Milton is shown to be a strong believer in the inevitable and desirable progress of civilisation along with capitalism, and possibly imperialism. His philosophy is best summed up by one of the first things he says to Arthur Morgan: "I enjoy society, flaws and all." He despises Dutch van der Linde, believing him to be a savage, communist, silver-tongued and a parasite that preys on the civilised and weak (all of which he technically is). He is ruthlessly determined to see Dutch suffer for all of his crimes, to the point where he is willing to degrees of clemency and good luck for gang members if they turn him in.

Because of his stature in a government backed organisation, it can be said that Milton is a little less ruthless as the gangs he hunts. In short, he is actually wise and ambitious, but also pervy and sadistic. It could also be speculated that his fellow Pinkerton agents dislike him, as agent Johns quips contemplatively that he'd "like to find a poisonous snake for him". He's also extremely smug up until his death and mockingly cordial with his enemies, in a strong attempt to seem professional, something he usually succeeds in. One of many more of Milton's redeeming traits is that he's extremely confined to the law, a standard his sponsor, Leviticus Cornwall doesn't hold in comparison.

Despite this, given for the game's setting, he's proud of the genocide inflicted on the Native Americans.

Trivia

 * Milton dresses better and fancier than both, Archer Forman and Edgar Rose, despite the Pinkertons being way older than the FBI. He also has a better hairstyle.