Winston was born in Passaic, New Jersey. He lived in Edison, where he attended Bishop George Ahr High School, and moved to Millstone Township in the late 1990s.\n', '

He attended Rutgers University where he participated in college baseball. He holds Rutgers career records for victories (26), innings pitched (278) and complete games (22). He was inducted into the Rutgers University Hall of Fame in 2000. On June 1, 1988, Winston was drafted by the Montreal Expos in the 18th round of the 1988 amateur draft, and he signed with them on June 7 of that season. On October 15, 1994, Winston was granted free agency. On December 8, 1994, he signed as a free agent with the Pittsburgh Pirates. He was again granted free agency on October 15, 1995. On December 20, 1996, Winston signed as a free agent with the New York Mets. He was then released by the Mets on March 31, 1997, before playing a game in their organization. On April 7, 1997, he was signed as a free agent with the Philadelphia Phillies.\n', '

Winston made his major league debut on September 10, 1997, with the Philadelphia Phillies. On the day of his major league debut, the Phillies were playing against the New York Mets at Shea Stadium, with 13,257 people attending the game. In the bottom of the eighth inning, Winston was called upon to replace Ken Ryan, for whom Kevin Sefcik had pinch-hit in the top of the inning. He pitched one inning, striking out one batter, allowing four earned runs, three hits, and two bases on balls. The Phillies lost to the Mets, 10-2. He played his last major league game on June 25, 1998. After the season, he was not offered a contract, and became a free agent on October 15, 1998. He signed with the Los Angeles Angels of Anaheim on November 18, 1998, but he never played in professional baseball after that.\n', '

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