Red Dead Redemption Episode 2: This is Armadillo, USA

"Bonnie asks John of his connection to Bill Williamson but John would rather not talk about that time, lest it bring trouble. Bonnie then insinuates that a city man like John must have some exotic secrets, then challenges him to a horse race."
"As John approaches Bonnie MacFarlane's house, she will ask him to take her into town, that is Armadillo."
"John wants to capture or kill Bill Williamson. Leigh says that would be very hard, as it's already tough enough for him to keep Armadillo safe. John then offers to help him with some goons hanging out at the saloon."