Slowly working your way up to becoming the second Underboss of the Van der Linde gang was a feat in and of itself.

After the Blackwater incident (you were with Arthur at the time out hunting, and wasn't there), and after finally moving out of Colter, the gang had found itself in the nice little spot of Horseshoe Overlook. Where you had went and got to work: doing odd jobs, robbing whatever coach you could find, breaking into the Valentine gun store in order to steal yourself a Lancaster repeater (was a damn good gun), earned yourself a rather nice moniker. Which got you as a second Underboss, and working right alongside some of the big players in the gang. Which led you out on a certain task: transport an oil barrel back to camp in order to set up a train robbery. John's idea (first time he ever had one).

As you were riding to meet with Arthur to transport the wagon...he wasn't there. So you rode over to the depot, finding a bunch of dead guards...and a wagon missing a wheel. Once he saw you, he shook his head, and stood,

Arthur: "I broke the goddamn wheel..."