The film was based on an idea by executive producer Dana White, best known for his association with Ultimate Fighting Championship, who had lived in Boston and wanted to tell a story about the Irish mafia gang of Whitey Bulger.[2] He brought on Chris Bertolini to write the script and sold it to Spike. In an interview, White stated that he understood the audience to be "18- to 34-year-old males who are the ones watching Spike TV". He further stated, "We're going to push the limits on this show, like Nip/Tuck and The Shield — violence, sex, bad language. We're going to see how big Spike's balls are on this one."[3]
Filming took place in Boston in late 2008.[4] The working title was The War of '04.[2]
Director Walter Hill had his name taken off the film and was credited as "Rob Marcus". Hill's biographer calls the film "unfocused and chaotic."[5]