When John Connolly is arrested by FBI agents, the scene starts with a long pan of his condo building with Boston Harbor in the background. Moving from left to right, a modern Euro-styled yacht appears in the background. When Connolly walks toward the agents, the yacht is gone.
When Whitey and his crew are pulled over by a marked Boston patrol car, the cruiser's license plates are solid blue with white letters and the word police written at an angle. At the time, they would have been solid white with blue lettering, like the plates on Whitey's and Connolly's cars.
Although the Angulios' address in Boston's North End was 98 Prince St., the street used to characterize events happening at that address in the picture, was actually a side street nearby Prince St. Probably a lot easier to shoot on the little side street than it would have been to shoot the scene on Prince St., which is longer, and a lot more heavily traveled than the street where the scenes were actually shot.
The epilogue states that William Bulger later became Chancellor of the University of Massachusetts. William Bulger was President of the University of Massachusetts, a position overseeing the entire UMass system. Chancellor is a lower position, and each UMass campus has one.
One report shown on screen refers to Newton High School. Newton, Massachusetts has had two high schools since 1960: Newton North and Newton South, although Newton High School was renamed Newton North High School in 1974.