After the Van der Linde gang sets up camp in Horseshoe Overlook, the player can travel to Valentine. By entering Keane's Saloon, he meets biographer Theodore Levin who is having a conversation with Jim "Boy" Calloway, a supposed legendary duelist back in the Wild West. Calloway drunkenly passes out and Levin vents his frustrations on the lack of details he's received from Calloway so far.
The protagonist strikes up a conversation with the biographer who then offers him half the proceeds of his book to find and interview other legendary duelists about their interactions with Calloway. Levin gives the protagonist pictures of four people: Flaco Hernández, Emmet Granger, Billy Midnight, and Black Belle. Levin asks him to speak with them about their gunslinging days and get a photo of them. Aware of their likely sour dispositions, Levin suggests to him to "shoot them" if they give him trouble.
The player is tasked with finding four legendary gunslingers from the days of the Wild West. Levin gives him photographs with updated notes on where to find them. The locations of the gunslingers will be marked on the map once the photos and notes have been inspected. These gunslingers can be found in any order.
Emmet Granger is located on a small farm south of the Horseshoe Overlook camp. He can be found near his pig stables and will not attack on approach. The protagonist mentions the book and Calloway and Granger becomes irritated that the book isn't about him instead. When the player asks for some stories, he promises to share some if he cleans the manure out of the pig stables. While the player cleans the stables, Granger briefly recounts his cruel deeds but refuses to account specifics of Calloway. After the player finishes the task, Granger refuses to share more details, merely complaining that the book should be written about him. The protagonist isn't amused and grabs a stick of dynamite and plants it in the manure shed. He lights the stick and it explodes, coating Granger. Granger becomes irate and a duel initiates. Kill him and take a picture of his corpse. His custom revolver, Granger's Revolver, can be obtained after his defeat.
Flaco Hernández can be located in a remote cabin to the north near Cairn Lake. The player approaches a modest camp with members of the Del Lobo Gang. The player can kill the members of the Del Lobo gang outside. Once they have been dealt with, approach the cabin. Alternatively, the player can talk to Del Lobo gang and can threaten them. They will allow you to enter the camp without being attacked.
The protagonist calls to Flaco through the door and asks him to tell him about Calloway. Flaco comes out and says "Here's your message" and hovers near his revolver, leading to a duel. Kill him and take a picture of his corpse. His custom revolver, Flaco's Revolver can be obtained after his defeat.
Billy Midnight was last seen near the Rhodes train station. Approach the clerk in the station and ask of Billy's whereabouts and the clerk will state the gunslinger is somewhere in the next two trains. Wait outside and board the first train that arrives. Billy can be found in the bar car of a train. The player approaches and asks him about his gunslinger days but Billy is frighten and runs off, thinking the player has been sent to kill him. Follow him through the train and eventually onto the roof. With Billy cornered, he draws his weapon for a duel. Kill him and take a picture of his corpse. His weapon, Midnight's Pistol, can be obtained after his defeat.
Black Belle resides in a hideout in Bluewater Marsh, north of Saint Denis. She is still on the run and is holed up to prevent bounty hunters from killing her. When the player approaches the porch of the house, Belle asks if he's a bounty hunter. When he declines, she spots two bounty hunters coming from a distance and tells him he led them here. Belle promises to tell him she'd tell him a story if he follows her orders. She tells him the whole property is wired with explosives and to flip the switch when she gives the word. A large scale gunfight ensues with Belle and the player killing waves of bounty hunters. Defeat the waves of enemies and watch out for the Gatling gun. After the fight dies down, he asks her about Calloway. She says he didn't do much of the fighting and his reputation is overblown. The protagonist asks her for a picture and she obliges before getting on a horse and riding away.
Return to Valentine
The second part of the mission tree will initiate after completing the Chapter 4 quest "A Fine Night of Debauchery". Return to the Valentine Saloon and the bartender tells the player that Calloway was last spotted in Saint Denis. Head to Saint Denis and look for a large ferry boat on the south-east side of the town. The player is then told about Slim Grant, an old rival of Boy Calloway who killed his cousin, Levin wants to see a face off between Calloway and Grant to prove he is a legend.
Slim Grant has became the state marshal operating out of Annesburg. The player interacts with a deputy who told him that Grant has been missing for a few days after he went out searching for outlaws. The player then locates him and must kill the outlaws who kidnapped him and then take state marshal Grant to be confronted by Calloway. However, Grant refuses to fight Calloway, resulting in an enraged Calloway shooting him in the back. Calloway then goes crazy and threatens to kill both the player and Levin before challenging the player to a duel. Once Calloway is killed Levin is initially shocked but is then surprisingly happy, saying he no longer has to deal with him. He does, however, bemoan the fact that the last true gunslinger might have died. The player then has the money sent to Tacitus Kilgore or Jim Milton depending on which character they are playing as. A few days later, $350 will be received in the mail in Levin's thank you letter.