Menhart was born in St. Louis, Missouri, on March 25, 1969, and grew up in Mystic, Connecticut. He attended Robert E. Fitch High School in Groton, Connecticut, where he played baseball, basketball, and soccer. He also played American Legion Baseball in New London, Connecticut.\n', '

After graduating from high school in 1987, Menhart played college baseball, pitching for Western Carolina of the Southern Conference for three seasons. During his college career, he had a 19-17 record overall – 11–6 in Southern Conference games – with 214 strikeouts. He led the Catamounts in strikeouts in each of his seasons and in innings pitched twice. In 1988, with an 8–3 record and a 3.55 earned run average (ERA), he was a first-team All-Southern Conference player. He was named the Southern Conference Tournament Most Valuable Player in 1989 after he threw a five-hitter with 10 strikeouts in the semifinals versus Appalachian State. During his college years, Western Carolina won the Southern Conference championship in 1988 and 1989.\n', '

Menhart opted to forego his senior year of college and enter the 1990 Major League Baseball draft. On June 4, 1990, the Toronto Blue Jays selected him in the eighth round of the draft as the 231st pick overall. He signed with the Blue Jays on June 6, 1990. He began his professional career with eight appearances – all starts – for the Class A-Short Season St. Catharines Blue Jays of the New York–Penn League, pitching to a 4.06 earned run average (ERA) over 40 innings, with 38 strikeouts and 19 walks and a record of 0–5. He then was promoted to the Myrtle Beach Blue Jays of the Class A South Atlantic League, where he pitched to a 3–0 record and a 0.59 ERA in ​30 2⁄3 innings over four starts – one of them a complete game – and one relief appearance, striking out 18 and walking five.\n', '

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