As soon as you complete the Can a Swindler Change His Spots? mission in Red Dead Redemption, this quest will immediately begin. Dickens will tell you about the urgent need for money to improve his wagon. Ride with him to Rathskeller Fork to get the promised cash. Upon arrival, you will realize that you are in for a horse race. Dickens forces you to participate again. Run to the starting point of the race, whistle to call your horse, and wait for the starting whistle. The rules are the same: you will be disqualified for shooting at spectators or other participants.
Your goal is to finish first in the race. Fortunately, your horse is significantly faster than the others. Follow the designated path strictly, without deviating from the route, and reach the finish line. After that, talk to Dickens to receive a reward of +100 points to the Fame parameter.