On June 2, 1994, he was drafted by the St. Louis Cardinals in the 6th round of the 1994 amateur draft. On July 31, 1997, he was traded by the Cardinals with Eric Ludwick and T. J. Mathews to the Oakland Athletics for Mark McGwire. On July 31, 1999, he was traded by the Athletics with Jeff D'Amico and Brad Rigby to the Kansas City Royals for Kevin Appier. On June 17, 2001, Stein fanned eight straight Brewers for the Royals, and 11 in five 2/3 innings, but Milwaukee defeated Kansas City, 5-2. Only Nolan Ryan (twice), Ron Davis, and Roger Clemens had struck out eight in a row in the American League. Tigers pitcher Doug Fister would break this record on September 27, 2012, striking out nine Royals, but receiving a no-decision in a 5-4 Detroit victory.

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