Drafted in the 19th round (568th overall) by the Pittsburgh Pirates in 1998.
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Bennett gained little recognition as a prospect in his first five seasons in the Pirates system, repeating both the Rookie and high Class A levels. His career took off last season when Pittsburgh switched him from starter to reliever. He pitched well in Double-A, and though he struggled in Triple-A the Brewers still saw enough to take him in the major league Rule 5 draft in December. He has to stick on Milwaukee's 25-man roster all season, or else clear waivers and be offered back to the Pirates for half the $50,000 draft price. Relieving agrees with Bennett because he can throw harder in short bursts instead of worrying about pacing himself. Bennett's fastball jumped from 90 to 95 mph in the bullpen, giving him the out pitch he lacked as starter. He also throws a good slider that prevents hitters from sitting on his fastball, though he didn't use it enough after making the jump to the Pacific Coast League. It wasn't a surprise that Pittsburgh lost him in the Rule 5 draft, though there's some concern that he had a sore shoulder in the Arizona Fall League. Considering how hard he now throws, it's not out of the question that Bennett eventually could emerge as a closer.
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