A multi-sport star in high school, Pennyfeather turned down a football scholarship with Syracuse University in order to play baseball at that same school. After his sophomore year at Syracuse, Pennyfeather signed with the Pittsburgh Pirates in 1988 as an undrafted amateur free agent and began his professional career with the Pirates\' affiliate in the Gulf Coast League.\n', '

Listed at 6 ft 2 in (1.88 m) tall, weighing 195 pounds, and batting and throwing right-handed, Pennyfeather made his major league debut on June 27, 1992. During his major league career he appeared in 40 games over those three years and collected nine hits, including a double.\n', '

In 1994 he was claimed on waivers by the Cincinnati Reds, who traded him to the California Angels for Eduardo Pérez in 1996.\n', '

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