Matt Damon Rory Casey Affleck Cobby Hong Chau Dr. Donna Rivera Michael Stuhlbarg Mr. Besegai Paul Walter Hauser Booch Ving Rhames Frank Toomey Alfred Molina Richie Dechico Toby Jones Alan Flynn Jack Harlow Scalvo Ron Perlman Mayor Miccelli André De Shields Mr. Kelly Toby Onwumere John Wayne Rob Gronkowski Rob Gronkowskoi Natalie Carter Mrs. Haggerty Richie Moriarty Jerry the Grocer David Gborie Bouncer Slate Holmgren Dave Wedge Tommy Nohilly Police Commissioner Jason Furlani Cabinet Member Nathaniel Wood Massachusetts Trooper #1 Mike Bash Boston Police Officer Shawn Fitzgibbon Quincy Cop Jerry Kernion Fire Monitor Nik Walker Hero Fireman Michael Rodrick Police on the Roof Don DiPetta Officer at Airport Billy Smith New Police Commissioner John Noble Barrack Photographer Robbie Dema Border Patrol Mountie #1 Robert Harvey Border Patrol Mountie #2