He quickly moved through the ranks competing in four cylinders, modified four cylinders, NASCAR Late Models at the highly competitive Nashville Speedway and most recently, the ARCA RE/MAX Series.
In February 2003, Montgomery earned his first professional victory when he took the checkered flag at the Advance Auto Parts 200 Automobile Racing Club of America (ARCA) event at Daytona International Speedway.
He started to turn heads while competing in the ARCA Series in 2002. He earned four top-five and ten top-ten finishes on his way to a fourth-place finish in the point standings.
Montgomery set a record as the youngest driver to win a pole at Daytona when he paced the ARCA 200 last February. In 30 career ARCA starts, he has one win, six top-five and twelve top-ten finishes and finished second in the ARCA Rookie of the Year standings.
The success attracted attention from a very unlikely source, as rock legend Alice Cooper came onboard with Montgomery as a marketing partner in summer 2002. Montgomery's efforts also attracted the attention of Clarence Brewer, owner of Brewco Racing, who signed him to a seven-race Busch Series deal in 2003.
In early 2004, Montgomery was signed by Bobby Hamilton to drive the No. 8 Dodge in the Craftsman Truck Series.
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