Heilman was born in Logansport, Indiana and attended Logansport High School, where he was a letterman in baseball. As a senior, he was a team M.V.P. and an All-State selection. Heilman graduated from Logansport High School in 1997.\n', '

After a successful college career at the University of Notre Dame, he was selected by the New York Mets in the first round of the 2001 amateur draft with the 18th overall pick. Heilman was a management information systems and philosophy major in the Mendoza College of Business at the University of Notre Dame.\n', '

He was drafted by the New York Yankees in the 55th round of the 1997 Major League Baseball Draft and by the Minnesota Twins in the first round (31st overall) of the 2000 Major League Baseball Draft, but did not sign either for either team.\n', '

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