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Damon was only a 20-year-old minor leaguer when an advertising agency cast him in a commercial with Kansas City Royals legend George Brett. His short swing and blazing speed excited scouts and coaches who hoped he could replace Brett as a mainstay of the team. His growth took time, but in spite of the Royals' repeated losing records, Damon improved his on-base percentage every year. While his throwing arm impressed no one, his ability to cover vast centerfield acreage did.

In 1999 the Royals had just begun to rebuild the team with potential stars like Carlos Beltran, Jermaine Dye, and Mike Sweeney. As one of the few veterans, Damon felt pressure to be a leader in the clubhouse and on the field. The extra strain led to a slump at the plate early in the season. But on April 28, 1999, Damon's life changed forever: his wife gave birth to twins. From that moment he went on a tear, including a 13-game hitting streak in which he went 22 for 50, leading the Royals to a 9-4 record. Exhausted from the feeding and diaper changing that came with a pair of newborns, Damon no longer out-thought himself at the plate, making his swing more natural.

Damon had hoped to remain in Kansas City, but the Royals' financial woes prevented them from signing him to a long-term deal. In 2001 he went to the Oakland Athletics as part of a three-way trade with Tampa Bay. (EPW)