Chapter 5 is among the most unique story chapters in the Red Dead Redemption 2 story mode, as you will have lost all your weapons and your horse, and will need to deal with enemies in the first few missions of the chapter with extremely limited resources. This doesn't last long, thankfully, and you will soon be back in America to reclaim everything that you lost after the failed bank heist at the end of Chapter 4.
Chapter 5 is among the shortest story mode chapters, as it only features 8 main story missions, with an additional mission that can be completed in either this chapter or Chapter 6. Like for all the other story mode chapters, these missions all come with requirements that must be cleared in order to obtain a Gold Medal.
These requirements can be cleared during the first playthrough or during repeated ones, which can be started by accessing the Progress section in the main menu. Repeated playthroughs, however, give you a limited weapon loadout and no tonics, so it's much more difficult to obtain Gold Medals this way. It's much better to make a manual save before each story mission, play through it once to learn about the requirements and then reload the save to play it again with all your weapons and items.
Welcome to the New World
Welcome to the New World is the first story mission in Chapter 5 and the 57th mission in the Red Dead Redemption 2 story mode. It's unlocked automatically after completing the Banking, the Old American Art mission in Chapter 4.
At the very beginning of the mission, Arthur will wake up on a beach, completely alone. As soon as you regain control of your character, continue walking until you spot smoke from a campfire. Head over to the source of the smoke to meet back with Dutch and the others, who all have managed to survive.
The moment will turn sour quickly, however, as Arthur and the rest of the gang will be captured by a patrol. All of them will be chained and forced to go together with the soldiers.
To get the Gold Medal for this mission, you must not fall behind while walking with the chain gang. This requirement is extremely simple to clear, as all you have to do is to continue walking and follow the line. After a short while, rebels will appear and free all of the captured. Arthur will take advantage of the situation to grab a pistol and help the rebels deal with the soldiers.
To get the Gold Medal, you must get 10 headshots. You will start with a full Dead Eye bar so activate the ability, mark enemies' heads and let loose. As you have no tonics, you may have to be more careful than usual while using Dead Eye, as once the bar is depleted, you can only restore it by performing well-placed shots on enemies.
Reinforcements will eventually arrive, and Arthur and the rest of the gang will have to follow the rebels' leader to a new position, which you will have to defend. Continue going for headshots to clear the requirement for the Gold Medal, and always keep an eye on the sides of the hill, as enemies will try to catch you unaware. After the fight has gone on for a short while, enemies will start fleeing: use this chance to get some more easy headshots in.
Once the enemy has retreated, you will be introduced to the situation in Guarma by Hercule, the rebels' leader. After the cutscene is over, the mission will be complete.
A Kind and Benevolent Despot
A Kind and Benevolent Despot is the second story mission in Chapter 5 and the 58th mission in the story mode. It becomes available after completing the Welcome to the New World mission earlier in the chapter. To begin the mission, you must speak with Dutch at the marked location on the map.
While most of the gang made it out safe, Javier didn't, and he is a prisoner of Colonel Fussar, the despot ruling the island. Dutch has no intention of leaving Javier to his fate and comes up with a plan to infiltrate the fortress and rescue the fellow outlaw.
Once you are done talking with Dutch, follow him to get near a cave where a contact of his is waiting to take the two to the fortress. Follow the contact for a short while until you reach a metal door. Help Dutch open it and proceed to get into the fortress. Here, you will see a cutscene of Colonel Fussar interrogating Javier.
As there are way too many enemies for Arthur and Dutch to make it out alive, they must create a distraction. Follow Dutch and kill enemies as prompted. Always remember to go for a stealthy approach, otherwise, you will fail the mission.
Once inside of the sugar refinery, wait for the guards to move out of your way to kill them silently together with Dutch. After they are dead, it's time to sabotage the refinery: head over to the location marked on the map and open the valve when told to, then close the shutters and slash the sack in the east side of the room. Rejoin Dutch, head out of the refinery and wait for the distraction to do its job.
Once guards start rushing to the refinery, go to the cages and release Javier. Sadly, guards are already back and you will have to shoot your way through.
To get the Gold Medal for this mission, you must get Javier to safety in under 2 minutes and get 10 headshots. During this sequence, Dutch will carry Javier, and as long as you stay close to them, they will continue moving toward safety. Guards will be coming after you, obviously, so you'll have plenty of chances to get headshots.
Don't abuse Dead Eye, however, as the timer doesn't slow down when it's active: since there are no accuracy requirements for the Gold Medal, you can afford to miss a couple shots. Also, always make sure to take out the enemies that Dutch will point out from time to time, as they are in your way and will likely kill him if left unattended for too long.
More enemies will be waiting for you outside the fortress, so continue shooting them down and follow Dutch to make sure to clear the time requirement for the mission. Eventually, Dutch will ask you to stay behind and cover his escape. At this point, you will have cleared the 2 minutes requirement, so feel free to use Dead Eye as much as you want to deal with the remaining pursuers. Once they are all dead, Arthur will catch up with Dutch and Javier at the camp, and the mission will be complete.
Savagery Unleashed is the third story mission in Chapter 5 and the 59th mission in the Red Dead Redemption 2 story mode. It's unlocked after completing the Welcome to the New World mission earlier in the chapter. To begin the mission, you must head over to the location marked with the question mark on the map.
The main mission objective will be to rescue a group of slaves that has recently escaped the sugar factory. They are being pursued by Fussar's men, however, so there may not be much time before they are killed. Also, the killing seems to have already begun when Arthur reaches the marked area, as he sees a body hanging from a tree! He is then shot with a blow dart, which makes him lose consciousness quickly.
Fussar's men manage to capture Arthur after he loses consciousness and he will wake up in captivity. Not one to give up easily, the outlaw manages to find a way to escape. With your help, of course.
To get the Gold Medal for this mission, you must complete it within 5 minutes and 40 seconds. The time requirement is rather strict, so you must be extremely fast, especially in the following sequence.
As soon as you can control Arthur again, look at your hands and try to break free. Once the camera goes back to third-person view, start rocking back and forth with the left analog stick. Do this a few times to fall on the ground and break the chair. As you get up, grapple the guard and beat him to death. A cutscene will play, which you must skip to clear the time requirement for the Gold Medal.
During the cutscene, Arthur releases two slaves, Leon and Baptiste, who will then head to another location nearby to free the other slaves together with the outlaw. During this sequence, always crouch and wait for guards to pass by as Leon tells you. After a short while, you will reach an area where three other workers are being held.
To get the Gold Medal for the mission, you must release all the workers within 4 seconds. This is incredibly easy to perform with the help of Dead Eye: activate the special ability as soon as you see the workers and shoot at the ropes. The noise will attract the guards' attention, so Arthur and his companions will have to fight their way out.
To get the Gold Medal for the mission, you must get a total of 8 headshots. As the area has very good visibility and cover spots, it shouldn't be too hard to get them, even without Dead Eye. Whatever you do, however, make sure to take care of the sniper on the roof first, as he can deal a lot of damage in a single shot.
Once all the guards have been killed, a cutscene will play. Make sure to skip it to complete the mission without wasting any additional time to clear the time requirement for the Gold Medal.