- written, directed, co-produced by and starring Ben Affleck
- based on the 2012 novel of the same name by Dennis Lehane.
It's the Roaring `20s and Prohibition hasn't stopped the flow of booze in an underground network of gangster-run speakeasies. The opportunity to gain power and money is there for any man with enough ambition and nerve, and Joe Coughlin (Ben Affleck), the son of the Boston Police superintendent (Brendan Gleeson), long ago turned his back on his strict upbringing for the spoils of being an outlaw. But even among criminals there are rules, and Joe breaks a big one: crossing a powerful mob boss (Robert Glenister) by stealing his money and his moll (Sienna Miller).
- Max Casella [Digger Pescatore]
- John Cenatiempo [Gangster]
- Chris Cooper [Irving Figgis]
- J.D. Evermore [Virgil Beauregard]
- Remo Girone [Maso Pescatore]
- Brendan Gleeson [Thomas Coughlin]
- Robert Glenister [Albert White]
- Matthew Maher [RD Pruitt]
- Chris Messina [Dion Bartolo] (mentioned)
- Titus Welliver [Tim Hickey]