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Chapter 4 - Chapter 4: Breaking the Gang From Within

Watching Hosea walk away, Mike Walker let out a quiet breath.

He knew his plan was already halfway complete.

As long as Hosea and he could convince a portion of the gang to stand up and question Dutch's plan, that would be enough.

Because no matter what Dutch ultimately decided, Mike would benefit either way.

If Dutch stubbornly insisted on robbing the train, then just like the events of the game they would surely be targeted by Cornwall, who would hire the Pinkertons at a high price to hunt them down.

And this time, it might happen even faster and with greater efficiency.

After all, Mike hadn't died in Blackwater like he was "supposed to."

In the game, the reason the Pinkertons found the Van der Linde Gang so late was because Cornwall first lost a train, and then again lost his refinery to them.

Only then did he pour enough money into the Pinkertons to speed up the hunt.

In other words, the Pinkertons only went after the gang aggressively once the wealthy capitalist Cornwall demanded it.

But that was in the game.

Now, with Mike Walker in this world, everything had changed.

First, Dutch had killed an innocent woman in Blackwater, and the stolen money had been hidden away by him.

More importantly, Mac Callander, who should have died there originally, survived because Mike intervened.

Aside from the missing Sean, the Pinkertons had essentially achieved nothing.

In the original game, the Pinkertons appeared to follow Cornwall's orders closely, but early on, they actually took a rather passive approach toward the Van der Linde gang.

It was first pushed into a corner by the disastrous Blackwater heist; their situation only worsened as they repeatedly angered Cornwall, stirred up trouble in Rhodes, and eventually killed Angelo Bronte in Saint Denis.

The core reason was that during this era, the Pinkertons themselves were under enormous pressure.

They didn't have the manpower, influence, or political freedom to fully commit to chasing one outlaw gang.

At their peak, the Pinkertons had more active agents than the Army itself, making them a massive threat to federal law enforcement agencies.

If the Pinkertons handled everything, the federal agencies wouldn't get their share of power or benefits.

And because the Pinkertons were also being used to suppress labor unions and strikes, the government even passed the Anti-Pinkerton Act, severely restricting them.

By this time, the Pinkertons were strong on the outside, but weakened within.

They desperately needed a powerful outside backer and capitalists with deep pockets fit perfectly.

So for the Pinkertons, as long as they could survive, hunting the Van der Linde gang wasn't their top priority.

But now?

Now things were different.

The Blackwater heist money remained missing.

The Pinkertons didn't even recover the bodies of the robbers.

For the wealthy men who had lost such a massive sum, the Pinkertons were running out of excuses.

Fifteen thousand dollars in this era was far beyond the reach of ordinary citizens.

And if Cornwall decided to pressure them, the Pinkertons would absolutely give everything they had.

Which meant that if Dutch went through with the robbery… it would doom the gang even faster.

And that was exactly why Mike insisted on warning Dutch, pointing out the dangers of robbing Cornwall wasn't meant to save him.

It was meant to damage Dutch's authority.

If Dutch ignored their warnings and everything fell apart, the blame would land squarely on him.

Mike was confident that when things went wrong, he and his brother Davey Callander could rally several gang members to their side.

And if Dutch pressured by the gang decided to cancel the robbery, that wasn't a bad outcome either.

Even if the Pinkertons were more determined than in the original story, the West was huge.

If the gang stayed low-profile, and since New Hanover and Ambarino weren't under Pinkerton jurisdiction, things would remain relatively safe.

Mike would have enough time to plan an escape.

Once Davey's injuries healed, the two brothers could leave the gang.

But knowing Dutch's temperament both from memory and from the game Mike was certain Dutch would never abandon the robbery.

Not after he had already committed to it.

Dutch always claimed they were noble outlaws, different from common criminals.

He tried to maintain the appearance of a gentleman.

But a bandit is a bandit.

In this world, you can't be both a gentleman and a thief.

Mike looked at a distant homestead and murmured:

"Next, I have to see where this family stands."

Because if there was anyone in the Van der Linde gang who might side with him…

It would be them.

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