The Coldest Winter Ever is more than a hip-hop tale to show that "crime doesn't pay."" It digs into the truth of the hip-hop generation, shoveling out the realities of marginalization, materialism and sexism in the language of the streets. The reader follows the main character of this novel through a journey into the intimate details of hip-hop culture, experienced first hand by today's urban youth.
One of the most interesting aspects of the novel are winters dealings with men. "Winter attempts to be the quintessential femme fatale who always gets her man. However, in a truly sexist world, it is most likely the man who gets the woman, namely Winter, into many of her misfortunes (Hopson)."" In this novel we see winter interact with many men. Midnight, Santaga's right hand man is the first male we see Winter come across in the novel. He seems to be the perfect guy strong, young, goal oriented. A few early run ins with the law caused him to fall in to the life of crime with Santiaga. Winter shows her complete interest in him throughout the novel; however his loyalty to Santiaga and their five year age difference kept the two from ever hooking up. In actuality I got the impression he wasn't interested. Then we have Sterling. He's what she likes to call her sugar daddy. "Whatever little money he took home in pay, I took my 25 percent like I was his freakin' agent or something."" Coming from a sixteen year old girl this to many would seem quite unorthodox but in the "hood- this is all too familiar. Then there was Bullet a young up and coming dug dealer, gold teeth, and flashy clothes he seemed to fit the description of the "rough neck-, streetwise and edgy, something that inner city girls seem to go for these days. With all of her troubles throughout the book Bullet seemed to give her the most. Probably jealous of the fact he could never duplicated what Santiaga had done for her, he tries to show power over Winter through imprisonment and brow beating.