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In order to enlist the help of Captain De Santa in Escalera, John is first going to have to help the Captain out with a little rebel problem. You'll be asked to defend a train from rebels and then retake it once it has been hijacked.
You had to know the train you've seen rolling through the countryside was going to figure into a mission sometime, and now you've reached it.
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"Civilization, at Any Price"
Approach the President's mansion at the top of the hill in Escalera to begin the mission. De Santa approaches you and questions your intentions. He does his best Scarface impression and advances on you as his men hold you at gunpoint before he bursts out laughing and reveals the whole thing to be a practical joke.
De Santa will share a drink with you, and explain the trouble his country is having with a group of rebels. John explains his mission to De Santa, and De Santa suggests that the men John is searching for may be holed up with the infamous rebel, Reyes. He asks for your help, and promises the help of his commander in return.
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Ride to Chuparosa
You've got a choice of transportation here. You can hop on the wagon with De Santa or make your own way there on horseback. If you ride with De Santa, you can listen to his appraisal of the situation in the country, or choose to skip to your destination.
Once you've made it to Chuparosa, De Santa explains his plan. You and his men will escort an empty train posing as one filled with supplies in the hopes that the rebels will be lured out and you can deal with them.
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On the Job Training
Hop on a horse and follow the Captain to the train. The train engine has a lifebar that will appear atop your screen. You must ensure that the train survives the trip to Casa Madrugada. Follow the train and De Santa's men down the tracks.
About the time you leave the first canyon and enter the plains, a group of mounted rebels will attack. Use your auto aim and Dead Eye ability to take them out before they can get close to the train. Beyond the first group, a second group of three mounted rebels and three standing behind a group of rocks near the tracks will attack. Beyond them, three more rebels hide near the left side of the tracks. Use your mini map to spot them before you get too close.
Stay ahead of the train so you can move from side to side to take out rebel groups. You don't want to get stuck on one side while they attack from the other.
The upcoming tunnel looks like a good place for an ambush, so it should be no surprise when you face a large group of rebels on the exit side. Keep defending the train until it reaches Casa Madrugada.
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Un-Hijack the Train
Once you've reached the station at Casa Madrugada, the Captain will be very pleased with your peformance, and will invite you into the saloon. While you celebrate, a group of rebels hijacks the train and makes off with it. De Santa orders you to catch it and stop it before it crosses the bridge.
Get on your horse quickly and run toward the tracks. You're going to have to take out all the rebels on the train before you can retake it, and catching it quickly will ensure you have time to stop it before reaching the bridge. Take out the rebels as you move up the train. Once they're all taken care of, move up to the engine and press the "X" or "Square" button when prompted to jump aboard and stop it just before careening off the destroyed bridge.
For more mission walkthroughs, cheat codes, weapons guides, and more, check out our Ultimate Guide to Red Dead Redemption.