Konuszewski attended Bridgeport High School in Bridgeport, Michigan where he played baseball, basketball and football. As a junior in 1988, he had an earned run average of 1.47 followed by a 0.78 ERA in 1989. Over his final two seasons of high school he tallied 187 strikeouts in 129 innings. He was named all-state as both a junior and a senior and won multiple Michigan baseball player of the year awards.
After recruiting trips to Central Michigan, Texas A&M, Cal State Fullerton and Portland State, Konuszewski committed to play college baseball for Michigan. Konuszewski chose to attend Michigan despite being taken in the fifteenth round of the 1989 MLB Draft by the New York Yankees. At Michigan, Konuszewski formed a battery with Mike Matheny and would become the team's top starting pitcher. In 1991, he played collegiate summer baseball with the Falmouth Commodores of the Cape Cod Baseball League, where he posted a 1.79 ERA over 40.1 innings.
Konuszewski was drafted again in 1992, this time in the seventh round by the Pittsburgh Pirates. Konuszewski began his professional career in Pittsburgh's farm system. He was pitching what he considered to be his "best [season] as a professional pitcher" in 1994 when his progress was interrupted by the 1994–95 Major League Baseball strike. That offseason, he pitched in the Arizona Fall League where he had the distinction of striking out Scottsdale Scorpions outfielder Michael Jordan in a nationally televised game.

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