James attended Nacogdoches High School in Nacogdoches, Texas where he was a five-sport star. He was the leading scorer on the school's basketball team, had a 1.43 earned run average, struck out 80 batters in 73 innings pitched and received a scholarship to play college football as a linebacker at Oklahoma State. He was a high school football teammate of Kynan Forney. He was drafted by the Devil Rays in the 14th round of the 1996 Major League Baseball draft. He was assigned to the Gulf Coast League to begin his professional career.
In September 2000, James and a minor league teammate helped apprehend a bank robber near the Tyrone Square Mall in St. Petersburg, Florida and returned $7,600 to a SouthTrust bank.
James was called up to the Major Leagues for the first time on April 15, 2002 after pitcher Wilson Álvarez was placed on the disabled list and Travis Phelps and Jason Smith were demoted. He made his Major League debut on April 16, 2002 against the Detroit Tigers at Comerica Park. He started the game and pitched five innings, allowed two earned runs and picked up the loss. On May 17, 2002, James was placed on the disabled list with right shoulder tendinitis.

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