Calloway is the doctor for the town of Valentine who acquired his medical license in 1881. He sells tonics and cures to the player.
At some point, he became affiliated with the O'Driscoll Boys and had some sort of misunderstanding with the gang. In a letter to Calloway, an O'Driscoll gang member named Donal states that Colm O'Driscoll is glad about Calloway working with them again and reminds him that the gang was not pleased with him previously spreading rumors about them prior to the misunderstanding. Donal also implies that the gang has been stalking Calloway and his wife.
Events of Red Dead Redemption 2
Calloway runs the illicit protection business with the O'Driscoll Boys, which can be robbed by the player.
- Red Dead Redemption 2
- Looting the letter from Ben Calloway will result in a loss of honor.
- His medical license can also be found at the Old Light Saloon in Van Horn Trading Post.
- While shopping at the Valentine Butcher, the butcher will reveal that Ben Calloway and Jim "Boy" Calloway are cousins.