The Someday File — Jean Heller

Deuce Mora, a columnist for the struggling Chicago Journal, thinks she is searching for a human-interest story when she walks into a seedy neighborhood bar in suburban Cicero. What she finds is Vinnie Colangelo, an aging mobster living on bad beer, cheap bourbon and regret for the life he wasted.
Afraid for his safety in the boozy world he inhabits, Deuce gives him a ride home and thus seals his brutal fate. When Deuce learns the next day that Vinnie has been tortured and murdered, she is left with more guilt than she can shoulder, more curiosity than she can ignore, and in more danger than she can imagine.
Deuce's meeting with Vinnie thrusts her into the nexus of three murderous acts committed over nearly six decades. Is it possible they're connected? And if they are, can she uncover the truth without dying herself?
In a world where print newspapers are increasingly anachronistic and struggling to survive the onslaught of instant news delivery offered by 24-hour television and the Internet, Deuce must confront the mob, corrupt government, even her own editors to stay on the story.
Even more daunting is the need to face up to her own worst fears and to find the strength to see her mission through in the face of impossible odds.
It is a mystery Deuce will either solve or die in the trying.
This is a story that could only be set in Chicago, a city that rises as the principal character in any book it inhabits.
.