Years ago in high school, Ray Drecker (Thomas Jane) was athletic, popular and destined for success. Now, as a high-school teacher and basketball 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 attends a local self-help class whose mantra is to
identify a personal "winning tool" to market for financial success. 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.