the 1998 Major League Baseball Draft by the St. Louis Cardinals. In July , he signed a four-year, $3.5 million contract ($2.4 million signing bonus and a $1.1 million four-year guaranteed contract) to forgo the NFL and play exclusively baseball. He began his professional career with the Class-A New Jersey Cardinals, registering an 0–1 record in 3 starts. He was promoted to the Class-A Advanced Prince William Cannons on August 15. He made five starts, going 2–0 with a 2.79 ERA and earning his first professional win against Salem on August 21, after pitching six innings and allowing two solo homers with a walk and six strikeouts. In , he completed his first full professional season with a combined 9–11 record between the Arkansas Travelers (AA) and the Memphis Redbirds (AAA). He spent most of the season at Arkansas, where he was 7–11 with a 4.72 ERA in 25 starts. He tied for the team lead in wins (seven) and finished second with 150 strikeouts in 141 innings pitched. He struck out 10 or more in three of his starts and was a part of three combined shutouts. He allowed just one hit and had 11 strikeouts in 8 innings pitched during a win at Shreveport (8/6), leading to his selection as Texas League Pitcher for the week ending August 8. On August 27, he was promoted to Memphis and made two starts, going 2–0 with a 2.19 ERA. He earned a win at Vancouver by striking out 11 in 6 innings. On September 27, he was recalled by the St. Louis Cardinals but did not appear in any games. In , he struggled through an injury-plagued campaign in which he split time between the Memphis Redbirds (AAA) and the Arkansas Travelers (AA). He pitched only 56.1 innings on the year, posting 63 strikeouts and ranking eighth in the Cardinals organization with 10.1 strikeouts-per-nine innings pitched. He opened the season at Memphis, but got off to a bad start before being sent to Arkansas. He pitched well in 8 starts for the Travelers, allowing just one unearned run over 18 innings in one stretch, before being shelved with right elbow problems for more than two months. He returned to pitch three games at season's end, recording 15 strikeouts and 3 walks in 11 innings. He then played for the Scottsdale Scorpions in the Arizona Fall League. In , he opened