Winchester attended Clemson University from 1993 to 1996, where he was a 3-time Letterman. In 1995, he set what was then a school record for most pitching appearances by a Clemson pitcher with 33 (he now shares that record with 3 other former Clemson pitchers), all of them in relief; also in 1995, he had a Clemson single-season record ERA of 0.59. He finished his 3-year Clemson career with a 1.70 ERA.\n', '

Among his honors, Winchester was an ACC Player of the Week twice in 1994, and a member of the 1995 1st Team All-ACC Tournament team. Winchester was a Freshman All-American in 1993, an honor he shared with teammate, Shane Monahan. He was a Clemson All-American in both 1994 and 1995, as well as an All-ACC Selection. In 1995, he was an ABCA, Baseball America, and Collegiate Baseball All-American; he was both a First Team All-ACC player on the field and on the ACC Academic Honor Roll. That year, he was ranked 6th in the NCAA in saves with 14.\n', '

Winchester was drafted in the 14th round of the 1995 Major League Baseball Draft by the Cleveland Indians. He began the 1997 season in Class A, but quickly ascended through the minor leagues over the course of the season. He was traded to the Reds in midseason, and continued to move up the ladder, reaching the majors in September. He appeared in five games for the Reds, pitching six innings with a 6.00 ERA.\n', '

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