So Agent Milton works for the Pinkertons and makes it very clear there is no depth to which he will not sink to bring in Dutch and the rest of the gang.

But what if there’s a reason he is so fanatical about taking them down?

For this, I am going to tie together a couple popular theories. First, the theory that the Blackwater Heist was all a setup. I think it is possible Agent Milton made the plan to put the word out about an “easy” score with the intention of bringing the gang into an ambush. He set everything up, and judging by the way it ended up going, with a massacre of several Pinkertons and civilians while only taking down a few gang members, I find it likely he feels personally responsible for the carnage, and feels guilt about the people who died, which makes it personal for him.

Next, the theory that the woman in the back Dutch kills from RDR1 was killed the same way Heidi McCourt was killed in RDR2. This means Dutch held her hostage, and at the last minute executed her to create some chaos to escape in. However, this is also very reminiscent of the way Hosea was killed. Pushed out by his captors to return to his people, and shot in the back on the way. Was this Agent Milton getting some personal revenge for McCourts death, knowing Dutch and Hosea are like brothers? I would assume he witnessed the killing and was deeply affected.

Just something I thought of, let me know your thoughts!