don't look

Why did Blackwater fail? Dutch killed a mother in cold blood and then a massacre happened. The money was a set up and Dutch took the bait. Pinkertons swarmed the area and even Landon Rickets was there.

How did they find them at Horseshoe? By chance the Pinkertons found Arthur and Jack fishing, but was it really by chance? What happens in chapter 2?

A bar fight where fucking everyone in town is there, which afterwords Dutch is there

You sprang Sean free and there are bounty hunters who flee, you seriously don't think they talked??

Oh yeah, ARTHUR AND MICAH SHOOT UP A FUCKING TOWN

John killing Micah led to Ross and Fordham finding him. Any of the missions I mentioned practically led Milton and Ross to finding Arthur near Horseshoe.

How did the Gray/Braithewaite scheme fail?

The Grays knew what they were doing and so did the Braithewaites. They played both families instead of just one and instead of LYING LOW. Dutch's vanity, ego and sense of wanting petty revenge against Confederate white trash caused Sean to be killed and Jack to be abducted.

How did Saint Denis fail?

Dutch played Bronte in his own city, refused a favor(you do NOT refuse the Mob asking a favor) which caused the set up, then Bronte's murder and finally the Bank Robbery which they knew they were there.

The common theory is someone from the gang snitched and talked to the Pinkertons. Who exactly ? Micah ? Well, Agent Milton said they picked up Micah AFTER they came back from Guarma, so it could not have been him. Molly ? Again, Milton said they did pick her up (not mentioned when), but she did not say anything. I have also read theories that it might have been Agibail who snitched to which my response is - pure BS.

The truth is, nobody snitched, nobody talked. Yes. Yet the reaction of the Pinkertons was insanely fast, as if they knew the robbery was going to go down. How you wonder ? Well, it's simple. It's a long one, but have a read.

From the very beginning of the game, Dutch has been claiming that they are a few steps ahead of everyone else, but his arrogance proved to be the downfall. You see, the Pinkertons are not as dull and foolish as Dutch claim them to be, they are extremely efficient as a detective agency proven by the fact that they tracked down Arthur in Valentine. Now, when the gang moved to Clemens Point near Rhodes, the Pinkertons lost their trail for a while. However the gang contradicted their own plan of staying low by creating a huge chaos in Rhodes after killing both the Gray's and the Braithwaite's (best mission in the game btw). As soon as the word spread of the massacre of both the families in Rhodes all over the place, the Pinkertons connected the dots and knew that it could be the Van Der Lind gang who created the fuss and if so, they must be camping somewhere near Rhodes. Nonetheless, they found the gang hideout after sniffing around, a day or two after the Braithwaite massacre. At this point Agent Milton knew these bunch of people would not be too hard to find as all you need to do is to sniff around an area where there has been murder and madness.

Now to Saint Denis, Dutch dismissed Hosea's idea and went after Angelo Bronte just after the failed trolley station robbery. If he listened to Hosea, hit the bank at once, then vanished, the Pinkertons would have never caught on and they would be harvesting mango's in Tahiti. But a failed trolley station robbery followed by a huge shootout in the city killing dozens of cops then followed by a kidnapping and murder of the most powerful man in the city was enough chaos for the Pinkertons to realize it's the Van Der Lind gang. So they knew the gang is around this city and increased security in Saint Denis hoping that the next time they attempt a robbery, it would be the endgame. That is why as soon as the bank robbery started, the Pinkertons were all over the place.

It is also easy to explain why Hosea was captured and Abigail escaped. While causing the distraction, both of them did not realise how fast the response is going to be. The Pinkertons caught Hosea as his face along with other male members of the gang was known to them, specially Hosea, Dutch and Arthur as they have been the oldest members of the gang. But Abigail at this point was unknown to them so it was easy for her to walk right past them without them realizing.

Why did the gang fell?

Micah got into Dutch's ear, Hosea died and Arthur got sick.

Micah promised him riches and the glorious scores that appealed to Dutch's ego and vanity. But he wasn't the rat.

If he did rat, he was playing Dutch and the Pinkertons to get the Blackwater money and the money for turning in Dutch.

However.

It was all Dutch.

Dutch. killed Cornwall in broad fucking daylight. Arthur sprung John out of prison, they blew up a fucking bridge, Dutch led the Natives to their doom, Colm's execution turned into a bloodbath, an attack on the Oil Refinery which led to the deaths of Colonel Favors and Eagle Flies and to top it all with robbing the military. It's no fucking wonder the Pinkertons found them.

There was no rat. The Pinkerton’s were actually just good at their jobs. Micah being a rat makes no sense if you actually think about it. There’s NO WAY the pinkertons would have been ok with the death of Leviticus Cornwall as he was paying their wages. Micah and Dutch planned to kill him together. There’s also the fact that Micah straight up killed Pinkertons in the firefight that ensued cornwall’s death. Micah was an asshole but not a rat. Watch that scene with Milton and Arthur again…Milton would have most likely let Arthur go with that false information but Arthur decided to attack him. There was never a rat, they got played.

It's a combination of things on why they all failed.

Reason 1. Dutch's vanity and ego. Dutch desperately needed to be seen as this great American hero. He cares more of the thrill of “one last score” it’s all about his ego and how he has to be seen as this Evelyn Millerian figure. This great American Literature hero when he’s really as bad as the greed that he says poisons America. He never cared about the people in the gang. It was the prestige of the name "The VAN DER LINDE Gang" HIM. He wanted to be seen as this infamous outlaw and righteous leader. He didn't care about the people in the gang. Arthur? He was dying and he didn't care. John? He wanted him to hang. Abigail? He left her behind the first chance he got. Micah killed Susan RIGHT IN FRONT OF HIM and Dutch didn't care. He considerd Mary-Beth, Pearson and Uncle leaving as a betrayal. Dutch never cared for the people within the VDL Gang. He cared what they could do for him and the glory they could bring him. It was never of settling down to become farmers, it was always about the thrill of being an outlaw the that great big score.

There are a lot of people who think if Hosea never died, then Dutch never would've lost it. He was always bad. He just had good ways of masking it. Hosea failed at every venture to talk out of getting Dutch to see sense and avoid bloodshed. If Hosea lived, there is a very good chance that Dutch would've lost it and had Hosea killed. Either it would've been an accidental death like he tried by leaving Arthur behind, he would've went into full paranoid mode "You're trying to undermine me and take the group from me" and order Hosea to draw his gun and then shoot him. Like Hosea said "You'll damn us all" and he did.

Reason 2. Loyalty to a fault.

Loyalty held the gang together. Loyalty was what Dutch valued - blind, obedient loyalty. “He had a plan,” after all.

Doubt broke the gang apart. Dutch became suspicious, uncertain of the faith of even his most dedicated friends. This undermined the entire operation and caused its eventual downfall.

“You’ll betray me, Arthur,” Dutch says, “You’re the type.” Dutch couldn’t be more wrong on that account.

Micah is named by the Pinkertons as a rat, but according to them, he wasn’t approached until after they’d returned from Guarma. So, by that timeline, the Pinkerton’s hadn’t needed a rat to foil their plans in Blackwater, or to find Arthur fishing by the side of a stream, or for the bank robbery in Saint Denis.

The Pinkertons always knew where Dutch was and what he was up to. They didn’t need a rat, especially not after their return from Guarma. So, why drop Micah’s name?

Well, the Pinkertons knew the gang was scrambling, that they were on the run, and that it was damn near impossible to arrest one of them at a time without a successful rescue of said gang member, ie Micah, John, Abigail and Sean. They are not the local sheriff’s office, after all. They are the federals and they want Dutch Vander Linde done in for good.

Staring down the barrel of a gun, why would a Pinkerton agent spill their collateral to the enemy? Arthur wasn’t even asking for any information at the time. Why would this agent, in his dying moments, tell Arthur that Micah was the rat?

Unless the agent knew the gang was on thin ice, and that loyalty was all that was keeping it together. He introduced what he hoped would be a final blow to the gang, accomplishing post-huminously what had been his career goal in life.

Also, why would Micah become an informant after Guarma? What were the promising him? After all, he stuck with Dutch and formed a new gang after Arthur died. He never took a big cut from the government and ran. He was a brown-noser and an asshole, but stood nothing to gain from becoming a rat.

Arthur hated Micah, so he took the bait. He wanted a reason to hate him, to have him kicked out of the gang. Micah was pragmatic and greedy and he hardened Dutch’s humanitarian side - the side that Arthur valued. But, Micah being a rat wasn’t the truth.

After all, we know who became a rat - John Marston.

Arthur’s readiness to believe a Pinkerton’s dying words proved the point of the narrative - the gang fell apart because they lost faith in Dutch, and because Dutch grew jealous and fearful as their doubts became apparent.

Loyalty kept the gang together, and its absence tore the gang apart.

Reason 3. "We didn't need a rat. We got sloppier than the town drunk."

The gang was careless. It got sloppy and their overconfidence and ego was their downfall.