Kraig returned to sprint cars in 2008 driving for Tony Stewart, following two years pursuing a career in NASCAR country. He shocked the sprint car world by taking the 2005 Knoxville Nationals, completing the first father/son tandem to win on sprint car racing's biggest stage.

He spent his youth watching his father, Steve, and learned much along the way. Tutored by his grandfather Bob, and Uncle Randy, Kraig started his sprint car career in 2000. The first four years were spent running regionally, before he ran the full WoO schedule in 2004, and claimed Rookie of the Year honors. He finished fifth in the WoO standings in 2005, before moving South to race.