Response to the challenge of LJ community: regrets.
L&O belongs to Dick Wolf, shit. I'm just manipulating the characters.
Jack never had the chance to tell her how much he loved her. Or sometimes he thought he didn't need it, because it still had time left to say that. If he hadn't been in that damn bar in that particular night, he would be with Claire right now. The drinks, the taxi cab that he took, the phone call that Lennie made. He thought about it every night before going to sleep, it was part of his routine.
Truth must be told: he screwed up everything. But if regret was a drug, Jack McCoy would be dead by now.