Years ago, as a student at Detroit's West Lakefield High School, Ray Drecker was athletic, popular and destined for success. Today, as a West Lakefield teacher and coach of the varsity basketball team (which is on an unprecedented losing streak), he's underpaid, uninsured and embittered that his wife of 20 years left him for her dermatologist, Ronnie Haxon. After fire damages the rundown lakeside home he inherited from his parents, Ray's fortunes reach an all-time low when his twin children Darby and Damon, who had been living with him, move in with their mom and her smug husband. Lonely, run down and at wit's end, Ray attends a self-help class, where the mantra is to identify a personal "winning tool" to market for financial success. After a not-so fulfilling encounter with fellow attendee Tanya Skagle, a would-be poet, Ray has a "eureka" moment. With the help of Tanya, the well-endowed Ray sets out to exploit his greatest asset in hopes of changing his fortunes.