In 1985 Grace was a junior at San Diego State when he was drafted by the Cubs in the 24th round and offered $5,000, but rather than sign he planned to go back to school for his senior year. His coach suggested that Grace spend his summer with the North Pole Nicks, in the Alaska League, where he could play without endangering his amateur status. Grace made $250 a month painting houses during the day and played ball (very well) at night. The Cubs took notice at the end of the Alaska League season and upped their offer to $20,000. Grace signed on the dotted line. Three years later he began a big league career (out of Double-A) that would include three All-Star appearances and four Gold Gloves.