He began his career racing in the Craftsman Truck Series in 2002. He ran two races that year, driving for Mittler Brothersteam. He finished 29th at South Boston and 30th at Phoenix after starting 12th in that race. He also made his BUSCH series debut at Memphis finishing 39th after starting 16th.
He jumped to the Busch Series in 2003 for a full-time ride with Bost Motorsports. Regan had some halfway decent runs with the underfunded team. 15th at Texas, 19th at the spring Darlington race and Gateway, and a 16th in the spring Dover race. However, the underfunded team opted for other drivers halfway through the year, and Regan searched for a job. Regan drove for George deBidart at Pikes Peak, finishing 40th after a Start & Park job. He also drove for the Jack McNally team in the Miami race, finishing 28th.
He continued to drive for the McNally team for various BUSCH races in 2004. He finished 17th at Nashville in the spring, and 19th at Gateway. He drove the #50 Michael Holigan car for three races in mid-Summer, and ended his BUSCH season with James Finch's #1 team at Pikes Peak, finishing a solid 15th. His best career finish in any major NASCAR series, to this date, was at Miami finishing 9th in the #06 John Boy & Billy Chevy for Team MRD.
Best Season YetEdit
Regan began the 2005 season with Dave Fuge's #19 team. However, after finishes of 32nd and 33rd, not to mention sponsorship lack, Regan was dropped. When Glynn Motorsports started their #65 truck team, they turned to Regan. In four races in that car, he had a 20th at Texas and a pair of 22nds at Mansfield and Dover.
He was promoted to the #58 Glynn Motorsports car, full-time, for the rest of the year. Regan put together 7 top-20 finishes in 21 starts for the team, his best being a pair of 15th at Loudon and the June Nashville race. From Dover to Phoenix, Regan put together an amazing streak of qualifying efforts. 6 top-7s in 7 races, and the other being a twelfth. Regan qualified 3rd 3 times in that stretch. However, it wasn't enough to keep Regan's job, as he was booted out for the season finale at Miami.
Meanwhile, Regan was back at MRD for the closing races of the season, finishing 29th, 33rd and 32nd in three late season starts for that team.
New Opportunites OpenEdit
Regan joined Team Rensi Motorsports' #35 Busch Series team hoping for good success with a top-tier team. However, Rensi struggled deeply in 2006. Smith was only able to muster one top-ten coiming at Charlotte. However, Regan caught the eyes of MBV Motorsports and after testing with the team, it appears as though Smith will join that operation in 2007.