Span bats and throws left-handed and is known as one of the premier leadoff hitters in baseball due to his exceptional on-base percentage. He is also one of the top defenders in the MLB for his ability to make difficult catches.

Span was selected by the Twins with the 20th overall pick in the 2002 Major League Baseball draft from Tampa Catholic High School. Span turned down just over $2 million from the Colorado Rockies in a predraft deal (who instead drafted Jeff Francis with the eighth pick) and his fall to the 20th pick cost himself around $800,000. Following his selection, Span signed with the Twins on August 15, 2002 which caused him to miss all of the 2002 minor league season. He started his minor league career in 2003 at Elizabethton, the Twins rookie-league affiliate. In 2004, Span was promoted first to the Gulf Coast League Twins in Fort Myers, Florida and, after only appearing in 5 games, for the Quad Cities of the Low Single A Midwest League. In 2005, he was promoted to Fort Myers Miracle, the Twins Advanced A affiliate, and then to the New Britain Rock Cats, the Twins Double-A affiliate. In 2006, Span returned to the Rock Cats, but was promoted Triple-A Rochester Red Wings in 2007.

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