Jack Bollinger was a member of a Dock Workers Union. He acted as the second-in-command, but ended up taking charge when the president was arrested for corruption charges due to sleuthing from Trudy Monk and Janice Ellinghouse. In actuality, he helped them with part of their journalistic investigation in ridding his boss of his power.
In 2006, Jack Bollinger got wind of Janice's death, and, panicking about the possibility of the records going public and the possibility of exposing his involvement to the President's ousting from power to his colleagues, he hired an actress named Cameron to masquerade as Trudy in an attempt to trick Janice's father, Zach Ellinghouse, into giving her the key. He managed to eventually get it, although in the process, Zach ended up killed by accident by Cameron. Cameron, shaken by the events, did not wish to continue, but he persuaded her to continue on, as well as heavily advising that she wear the wig, as Janice was blond as well.After managing to get into the storage locker that had her stuff in it, he originally intended to simply take the file that exposed his involvement. However, as the files and videotapes were not labelled, he decided to burn the lot instead. He panicked when he discovered that Monk was present. He threatened Monk with a gun out of paranoia when Stottlemeyer and Disher, after being alerted by Natalie, arrived. He attempted to gun down the police, but was shot. However, when he was shot, he also ended up shooting Cameron.