Craig's long and storied junior career began in 1997-98 after the Brandon Wheat Kings selected him in the 2nd round, 34th overall, of the 1997 WHL Bantam Draft. Although he only played one game at the major junior level that year, it was the beginning of a career that would span six seasons and see Craig crowned as one of the most decorated players in Wheat Kings history. After two decent seasons as a 16 and 17 year old, Craig exploded in 2000-2001 with 38 goals and 71 points in 70 games. That year he was named the Brandon Wheat Kings MVP, a distinction he would hold each of the following two seasons as well. In the summer of 2001 he was invited to attend the Canadian U-20 junior developmental camp. The following 2001-2002 season he scored 29 goals and 64 points in 52 games before suffering a career threatening knee injury. Despite the injury, the Lightning selected Craig in the 8th round of the 2002 NHL Entry Draft. After rehabbing his knee, Craig returned in the 2002-2003 season and took the WHL by storm as an overage player scoring 42 goals and 74 points in 60 games. Craig was named the captain of the WHL's Eastern Conference All-Stars for the CHL Hershey Cup and later was named to the First Team All-WHL team. Craig was also the recipient of the WHL Humanitarian of the Year award as his work with the community of Brandon was a central staple of his junior career.
In the summer of 2003 Craig signed with the Tampa Bay Lightning and attended his first training camp, after which he was initially placed with Pensacola of the ECHL. Craig's reputation as a leader preceeded him and he was immediatly named an assistant captain. His stay in the ECHL was brief, however, as Craig scored 8 points in 5 games with Pensacola and was named ECHL Player of the Week before being promptly promoted to the team's split affiliate in Hershey of the AHL. Craig played parts of his rookie season in Hershey on a line with veterans Eric Perrin and Shane Willis, but soon settled into a checking line role and finished the year with just 12 points in 61 games. It wasn't until the 2004-2005 lockout season with the Lightning's new full affiliate in Springfield of the AHL that Craig would fully blossom. Craig was named assistant captain of the team and responded by leading the club in scoring with 27 goals and 41 points in 80 games. At year's end he was named the Falcons' Best Player, Best Defensive Player and Most Popular Player. When the lockout lifted in 2005 and he returned to Lightning camp however he was among the first cuts and returned to Springfield where he was named team captain. Craig stayed with the Falcons for 28 games amassing 12 goals and 22 points before being recalled by the Lightning on December 17th, 2005. That night Craig played his first NHL game against the Detroit Red Wings and scored his first NHL goal.