I've used this type of analogy before but; Milton walked so Ross could run.

Milton the evil dirty police commissioner

In Milton's defense as horrible as he is he did give the gang several warnings in person whole being directly paid by Comwall who's a oil tycoon. He only killed them and made moves during the 3rd meeting at the bank after Bronte's men tipped them off. RSS however didn't give John any warnings took his family,taunted him at gunpoint with ways he could be executed, as well as ways they could implement punishment on Jack & Abigail as a "game". Ross didn't have a Ross aside from Nate Johns. As Ross was in charge of the BOI calling the shots so he was basically untouchable something not that offered to Milton. He was held in check and ridiculed over any failures by Cornwall betrating him by threatening to cut expenses to outright suggesting he'd look into the services of other law enforcement the job done against the Van Der Linde Gang.

No more obnoxious than Dutch was. To be honest Andrew Milton was really just the civilized version of Dutch Van Der Linde. Right down to the poetic speeches and sweet outfits.

Also, I love how everyone acts as if Lenny and Hosea didn't deserve to get gunned down for everything they did. How many people have they murdered over the course of their lives? I just see that as karma finally finding them.

True as it may be. We have ti remember they're outlaws. To the American Public they'd rather have corrupt lawmen/bounty hunters than murderous outlaws who rob and kill without consequences. If you're wearing a badge it gives you a certain prestige of leverage with the public, vs having a gun and roughing it I the wild with the law breathing down your neck. It's the same reason no matter how John/Arthur are played honorable are not the mass public view them as " Infamous Outlaws". while both Milton/Ross in death and in Ross case retirement are revered in high regard as glorified lawman who "preserve the peace of the West" . It's rather fitting and quite realistic as in the old days Marshalls/Lawmen were granted heavy leeway while outsiders particularly trouble makers. Whether minor crimes or not were often executed

@Bianca Bellaschnee

Lenny joined the gang very early he hasn’t done bad stuff like Micah and Dutch and even Arthur. Also Lenny mostly mugged rather than kill he also mostly killed the Lemoyne raiders. And cmon Hosea barely participated in any robberies.

And cmon Hosea barely participated in any robberies

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Yeah, sure in the game. But I'm not talking about what happened in the game. I'm talking about what happened before that and odds are Hosea was just as much of a murdering psychopath as Dutch was in his youth.

Yeah Hosea did slow down in age aside from the few con man style Robbie's with Arthur. However Milton & The Pinkertons are aware he's the 2nd in command and primary advisor to Dutch, making him the key conspirator/accomplice to many of the robberies. Which s furthermore why killing Hosea as sad as it was woked out ideally in the Pinkertons favor. It sent the Van Der Linder Gang & notably Dutch into a complete disarray. They were already getting sloppy since the ferry heist failed ,but after Hosea's death the gang had no clear direction , or went soley off of Dutch's paranoia and Micah's schemes leading them straight into the Pinkertons.

Pinkerton police commissioner Sherif Andrew Milton is a manic

OP is correct: Milton was not a cop. Like, literally: he was not any sort of government law enforcement official. He was a Pinkerton. The Pinkerton Detective Agency was a private security firm available for hire to anyone who could pay. This included the US government, who hired them as pseudo-FBI agents before the FBI existed, when there weren't enough government-appointed lawmen along the frontier, but also as strongmen and anti-union strike-breakers for industrialists like Andrew Carnegie.

Milton is a good representation of the sorts of divided loyalties a situation like that could cause: he wants to catch the criminals because the government wants to protect the public, and he's willing to use any means necessary because his other employer wants them gone so that they'll stop interfering with his business.