Brewington attended Junius H. Rose High School in Greenville and Virginia Commonwealth University. Selected by the Giants in the tenth round of the 1992 Major League Baseball draft, Brewington was recalled from the Double-A Shreveport Captains in July 1995 and made 13 starts from July 24 through season\'s end. He won his first two Major League starts, on July 24 against the Florida Marlins and July 30 against the eventual 1995 world champion Atlanta Braves. Altogether, as a rookie he compiled a 6–4 win–loss record, allowing 68 hits (including eight home runs) in 75⅓ innings pitched; he had the same number of walks and strikeouts (45).\n', '

However, Brewington failed to make the 1996 Giants and was ineffective in Triple-A, posting a 6–9 record and poor 7.02 ERA with the Phoenix Giants. He then was traded to the Kansas City Royals during the off-season. His struggles continued during the 1997 minor league campaign, with his earned run average ballooning to 7.84 in 23 games pitched. He was traded to the Milwaukee Brewers\' organization on July 29 and then released on April 25, 1998. Brewington did not pitch professionally during the 1998 season.\n', '

He then signed with the Indians and struggled through another difficult season in the minors in 1999, going 1–10 with the Class A Kinston Indians. But Brewington lowered his ERA to a respectable 3.84 and earned a promotion in 2000 to the Indians\' Triple-A affiliate, the Buffalo Bisons of the International League. Pitching exclusively in relief for the 2000 Bisons, he won his only decision, and further improved his earned run average to 3.02. Cleveland recalled him in June and used him in 26 games (all in relief). Brewington won his three decisions with Cleveland, with no losses, but allowed 56 hits and 19 walks in 45⅓ innings pitched (he struck out 34). He had no saves and his ERA was a high 5.36.\n', '

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