Batman was unable to save a friend caught in a gunfight. He remembered back when Jeremy Samuels was head of security at Wayne Enterprises and how he'd lost his wife and child in an accident which pushed him over the edge. After being paroled (for going on an armed robbery rampage), Bruce gave him a job only for Samuels to quit after two weeks. The BatSquad watched him - Batman knew he was planning something. Samuels had been hired by a man who worked with Penguin. Batman tracked him, but got caught in a diversion. The diversion enabled someone to watch him and track his moves. By the time Batman realized what was going on, the watcher had escaped.