Years ago in high school, Ray Drecker (Thomas Jane) was athletic, popular, and destined for success. Now, as a high-school teacher and bascketball coach, he's underpaid, uninsured, and embittered that his wife of 20 years (Anne Heche) has left him for her dermatologist. After a fire damages the rundown Detroit home he inherited from his parents, Ray's fortunes reach an all-time low when his twin children, who had been living with him, move in with their mom and her clean-freak hubby. Lonely, run-down and at wit's end, Ray attend a local self-help class whose mantra is to identify a pesonal "winning tool" to market for financial successs. After a not-so-fulfilling encounter with a fellow attendee - an ex-flame and would-be poet named Tanya (Jane Adams) - Ray has a "eureka" moment. With the help of Tanya, Ray resolves to take advantage of his greatest asset, in hopes of changing his fortunes in a big way.