You’ll find Dutch in alley near the trolley station back in Saint Denis, be sure to have lots of Snake Oils before you approach him and begin the mission. Once the robbery is underway, rob the three customers inside the station, you’ll have to suffer the small loss in honor if you want the Gold Medal Here.
Once that gang realises there is no cash and that Bronte has set you up, you’ll need to get out of Saint Denis and the group will board the nearby trolley. During this period you’ll need to score at least 10 kills however this is time sensitive as you wont be on the trolley long. Accuracy is not an issue here however you can score quicker kills by making use of Dead Eye and going for headshots. Pay special attention to the enemies on the balcony and change sides when necessary by pressing the [Square]/[X] button.
The trolley comes to a crashing stop and the fight takes to the streets on foot. Keep to cover and try to take out the enemies on the balcony first. You don’t need to worry about headshots or accuracy so feel free to go wild with your shooting, just be sure to stay in cover. Once the area is free of enemies to the left, Lenny and Dutch make a run for it, go with them and continue shooting any enemies in your immediate vicinity.
Eventually, you’ll jump onto a nearby police wagon and be pursued by mounted enemies. You’ll need to prioritize any that are approaching the wagon, if any board you then you lose the Gold Medal. You won’t be able to hit all of the enemies during this section so make use of Dead Eye to hit the immediate threats. Once you reach the bridge leading out of Saint Denis, Lenny remarks that it’s blocked as Dutch hands some dynamite over. Once Lenny throws the dynamite, you’ll enter Dead Eye automatically and have a short time to shoot it in the air as the final requirement for the Gold Medal.