James O'Leary

James O'Leary (otherwise known as Father O'Leary) is like a gangster, according to Andy Barber. James hires himself out for evictions, collections, and more.

He monitored the Barber home during the trial of Jacob Barber for the murder of Benjamin Rifkin and was threatened by Andy to leave their home. James also followed Laurie Barber while she was out jogging.

Andy spotted James outside the Middlesex County Courthouse where he flagged him to Pam Duffy. Pam stopped James in his car still outside the courthouse and asked him for his ID. He initially refused, but eventually conceded his identity. From this Pam gleaned more information which she later passed onto Andy.