Eckenstahler was born in Waukegan, Illinois. He attended Antioch Community High School in Antioch, Illinois and Illinois State University. He played for the Illinois State Redbirds baseball team in 1996, 1997, and 1999, although he did not appear in any games during the 1998 season. During his college career, Eckenstahler compiled a 14–7 record and a 5.40 earned run average in 36 games (31 starts).\n', '

Eckenstahler was drafted by the Houston Astros in 1995 and the New York Yankees, but he did not join either organization. After his senior college season, he was taken in the 32nd round of the 1999 MLB draft by the Detroit Tigers. Although he was drafted by Detroit on June 2, 1999, he waited nearly a full year before signing a contract with the Tigers on May 25, 2000.\n', '

Eckenstahler made his professional debut in 2000. He split the season between the low–Class A Oneonta Tigers and the mid–Class A West Michigan Whitecaps. He posted a 1.64 ERA in 8 appearances with Oneonta and a 5.79 ERA in 10 games (3 starts) with West Michigan. He split the 2001 season between the high–Class A Lakeland Tigers and the Class AA Erie SeaWolves. Eckenstahler posted a 1.50 ERA in only 4 appearances with Lakeland, whereas he recorded a 4–2 record and a 3.90 earned run average in 46 games with Erie.\n', '

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