Cirillo was born in Pasadena, California, to Howard Cirillo and Carol Grant. He has one step-brother, Adam Grant, who played baseball at UCSB. Cirillo attended Providence High School where he excelled in both baseball and basketball. Then, he enrolled at the University of Southern California after receiving little attention from colleges in his high school years. As a Trojan, he started out as a pitcher; however, he was moved to third base later in his college career. He was a member of the Phi Kappa Psi fraternity there and graduated with a degree in Communications.\n', '

Cirillo was drafted in the 11th Round by the Milwaukee Brewers. With the Brewers, Cirillo collected a .300 batting average or better for three seasons, including a career-high .326 in 1999. The same year, he added 198 hits (also a career-high) with 15 home runs and 88 RBI. His most productive season came in 2000 with the Colorado Rockies, when he posted career-highs in RBI (115), runs (111), and doubles (53); finished with 195 hits; and matched his personal-best .326 average.\n', '

On December 16, 2001, the Rockies traded Cirillo to the Seattle Mariners for Denny Stark, Brian Fuentes, and José Paniagua. Posting the lowest BABIP since his rookie season, he was ineffective with the bat but provided strong defensive contributions while in Seattle, ranked by UZR as the second best third baseman in the American League in 2002. In 2003, he continued to provide above average defense but again posted the lowest BABIP of his career (.226 compared to a .320 career average).\n', '

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