Valentine was born at Sunrise Hospital &Medical Center in Nevada to Deb Valentine on Christmas Eve in 1979. His biological father is a man who,as of 2005,he did not know. He was raised by Deb and her life partner,Doreen,who he also considered his mother. The family moved to North Babylon,New York when Valentine was only two years old. [1]
As a freshman,he attended St. Anthony's High School but later transferred to Deer Park High School in Deer Park,New York. He played primarily as a catcher and attracted little attention from college recruiters due to his mediocre offense. [1]
Valentine initially accepted a scholarship to play college baseball at Dowling College in Long Island but transferred after one semester to Jefferson Davis Community College in Alabama. At Jefferson Davis,he was named NJCAA All-Region XXII. [1]
He was drafted by the Chicago White Sox in the 26th round of the 1999 amateur draft out of Jefferson Davis and began his professional career that year.
Splitting time between the Arizona League White Sox and Bristol White Sox,Valentine went a combined 0–0 with a 5.57 ERA in 14 relief appearances.
He missed part of the 2000 season while pitching for Bristol,appearing in just 19 games with a record of 2–1 with 7 saves. Valentine greatly improved in 2001,going a combined 7–3 with a 1.79 ERA in 57 relief appearances. He split time between the Kannapolis Intimidators and Winston-Salem Warthogs,saving 22 total games and striking out 83 batters in 75