Riske was drafted by the Cleveland Indians in the 56th round of the June 1996 amateur draft. In January 2006, he was traded along with outfielder Coco Crisp, and catcher Josh Bard to the Boston Red Sox in exchange for reliever Guillermo Mota, third baseman Andy Marte, and catcher Kelly Shoppach.\n', '

Riske was traded on June 15 of that year to the Chicago White Sox for minor league pitcher Javier López. Theo Epstein commented that Riske was traded because the Red Sox had too many right-handed relievers, and needed a left-hander like Lopez. He throws a low-90s fastball, but due to his deceptive delivery, it appears even faster. He also throws a slider and a split-fingered fastball.\n', '

Having posted solid numbers the past two seasons, Riske continued to put up good numbers in the 2005 season. In 58 games and 72​2⁄3 innings, Riske had an ERA of 3.10 and a WHIP of 0.96. His strikeout total had noticeably declined over the past two seasons. In 2005 Riske experienced his first season in which he did not average more than one strikeout per inning pitched. He also is known for allowing home runs, allowing 11 in 2004 and 2005, and six in only 44 innings in 2006. Riske played a minor role with the Red Sox in 2006, mainly appearing in blow-out games before being traded.\n', '

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