Kiss Tomorrow Goodbye is the story of Ralph Cotter, an unquestionably amoral man who sees himself as intellectually superior because of his Ivy League education and for being born into an upper class family--although his pedigree is questionable and he steers clear of any proof when challenged by his minions. In one exchange he asks,
“Does it matter?” [where he went to college]
“You’re not ashamed of it , are you?”
“I think the college might be. I’m sure my career doesn’t reflect too much credit on the school. It does prove one thing, though it proves that I came into crime through choice not through environment. I didn’t grow up in the slums with a drunk for a father and a whore for a mother and come into it because it mistreated me and warped my soul. Every criminal I know--who’s engaged in violent crime--is a two-bit coward who blames society. I need no apologist or crusader to finally hold my lifeless body up to the world and shout for them to come observe what they have wrought.”
It’s easy to take this book as nothing more than a great "genre story," but McCoy’s use of the then topical subject of “nature verses nurture” is important to the times he lived as many of the “folk lore” criminals of the day such as John Dillinger and Baby Face Nelson were raised in "broken homes" and the apologists of the day explained their antisocial behavior on the hard times of the day.
The book opens with Ralph, along with a fellow inmate, Toko, breaking out of prison on a chain gang. They are aided by Holiday, the buxom gun moll cum femme fatale of the piece. Once successful, Ralph immediately starts pulling robberies in the unnamed town where he is hiding out. On his first job, he ends up being double crossed and when confronted by the police who at first seem about to shoot him. Holiday and Jinx instead, but take their money and tell the pair to take the first bus to Phoenix.
Ralph comes up with a scheme to turn the tables on the crooked cops by recording them on a phonograph talking about a bigger heist and presumably aiding the gang in the crime. He uses this to blackmail the high-ranking Inspector Webber and along the way meets and employs the lawyer, Mandon to help him setup his blackmail scheme. As he carries on a tumultuous relationship with Holiday, and plans bigger and bigger capers, Ralph (having taken on the alias of Paul Murphy) is soon revealed as not only wanting to gain riches but to climb socially as well.