Visit your brother's diner as a task for Fatty Welsh. When you talk to him, select the option to tell him the truth. At the end of the game he will attend your funeral and "Brotherly Love" will be earned.
After finding the moonshine brewery, cover the chimney and block the stills. Then, wait until it explodes.
Do not allow the bank robber rob the bank by choosing the following dialog options.
Convince William Jennings Bryan to speak at Mr. Merrick's event. To do this, choose the following dialog options.
Go to a bakery for Fatty Walsh, then talk to the women about the speakeasy business. After she appears with a gun, use the sack of flour and run outside. Wait for her to come out and get shot.