This is the story of Harold O’Brien, who at the age of 81 decides to embark on a life-long dream to compete in the 2000 National Checker Championship. The chances of him winning are slim, but the journey for Harold is monumental.
Raised on an Iowa farm, only miles from where he lives now, Harold was forced to leave home at the age of 17. He was quickly drafted into World War II and returned from the battle confused and bitter. He found himself a job working in a cement factory and stayed there for the next 30 years.
Harold never had a girlfriend, but at the age of 68-years-old met a woman named Norma, and in her, found the love of his life. Norma and Harold were married, and in 1994 she convinced him to enter the Iowa State Checker Championship. Harold believed he had no chance of winning, but with Norma’s encouragement and faith, he pulled off a series of miraculous victories and emerged the State Champion. For Norma and Harold, it was the proudest moment of their lives. Their happiness was short-lived, however, when Norma died in Harold’s arms a few months later.
Over the next six years, Harold struggled with depression. The only checkers he played was by himself, alone in his room.
One morning, in the spring of 2000, Harold begins to realize how disappointed Norma would be in his floundering life. With the news of the 2000 National Checker Championship, Harold decides to enter as a tribute to his wife. Gradually, Harold will once again begin to study the game he loves, as he prepares to make the 700-mile trek across the Midwest to Toledo, Ohio.