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His best season came in 2000 with Pittsburgh when he posted career-highs in earned run average, strikeouts, innings pitched, and games pitched as well as his only double-digit strikeout games and his career-best three-hit complete game despite the fact that he is a groundball pitcher.That year, Benson broke the record for most strikeouts in Pirates history for a right-handed pitcher.
He followed a strong rookie season in 1999 with an even stronger season in 2000, but those would prove to be the two best seasons of his career, as he underwent Tommy John surgery after the 2000 season.After 2000, he needed Tommy John surgery and missed the entire 2001 season.He started the last game at Three Rivers Stadium and the first game ever at Great American Ballpark.Subsequently, Benson was named College Baseball's Player of the Year, only the second (after fellow future major leaguer and Olympian Ben Mc Donald) to be so honored on the strength of his pitching alone.
As a Tiger, he won the Baseball America Player of the Year, and ACC Player of the Year.Benson lasted only four innings and surrendered five runs, and the bullpen gave up another six, en route to an 11–2 bludgeoning that kept the Americans from advancing to the gold medal game. he spent two years in the minor leagues with the Lynchburg Hillcats and Carolina Mudcats in 1997, and the Nashville Sounds in 1998.