Craig took a tortuous route to the majors. He began with the Brewers, but was released during the 2004 season.
He completed the 2004 season pitching for the New Jersey Jackals of the Northeast League, an independent baseball league.
Major LeaguesHe was signed by the San Diego Padres in 2005, and indeed, made his major league debut for them, on July 23, 2005.
He had a 2.20 ERA in 14 games for the Padres, and also spent time with the AAA Pacific Coast League Portland Beavers.
The Padres non-tendered Craig in December 2005.
Craig then signed with the Red Sox, as a minor league free agent, in January 2006.
He was promoted to Boston in the second half of the season, but pitched only 12 innings with them – posting a 3.75 ERA.
Craig began the 2007 league in the minors, and was promoted to Boston on September 1, 2007, but did not make an appearance and was sent back to Pawtucket on September 2 to make room on the team for Jon Lester.
On March 23, 2008, Craig was claimed off outright waivers by the Cleveland Indians and was added to the 40-man roster. He won the final spot on the Indians’ Opening Day roster, as a reliever.
On May 23, 2008, however, he was designated for assignment, and was picked up by the Minnesota Twins the next day.