DeWillis was born on April 13, 1965 in Houston, Texas. He attended Pearland High School where he played baseball, football and basketball. He was named an honorable mention on the 1980 and 1981 24-5A all-district basketball teams. For baseball, DeWillis, a catcher, was named to the all-state team in 1981 and 1982 was named first team all-district in 1983.
In May 1983, DeWillis committed to play baseball at Baylor University. However, he was drafted by the Toronto Blue Jays in the third round of the 1983 Major League Baseball draft and signed with Toronto. He reported to the Medicine Hat Blue Jays of the Pioneer League. He appeared in 56 games for Medicine Hat in 1983, finishing the year with five home runs, 21 runs batted in and a .242 batting average.
He was promoted to the Class A Kinston Blue Jays of the Carolina League in 1984, appearing in 122 games, before playing in one game with the Knoxville Blue Jays of the Southern League before the season ended. In January 1965, he was invited to spring training with the Blue Jays as a non-roster invitee. In March, he received attention from scouts and members of Toronto front office for his play in spring training, with Blue Jays vice president Bobby Mattick comparing DeWillis to Rick Dempsey. He was ultimately sent back to the minor leagues, and split the 1985 season between Kinston, Knoxville, and the Triple-A Syracuse Chiefs.

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