And thus lies the conundrum. Leo gave the girl the envelope with specific instructions to open it either after something happened to him (taken to mean after his untimely death) or when he told her to. Why would Leo have the instructions relayed to Dignam if he was still alive? Also, the envelope scene happens right after the scene where Matt deletes Leo's record. In that scene, Matt comes back to find that Leo has already left. He notices the envelope has been moved, and immediately jumps on the computer. Another important point to point out is that Leo's character was not trusting of Dignam throughout the entire movie. And finally, the size of the envelope indicates the containing contents are printed on 8.5" x 11" paper and then folded in half and stuffed into the envelope. The envelope itself was pretty thick indicating that there were more than one sheet of paper contained within the envelope. Lastly, the girlfriend was never shown in a scene with Dignam. How does she know what he looks like or how to contact him?
