A native of Bixby, Oklahoma,[2] Stewart began racing quarter midgets at age seven;[3] he began racing sprint cars at age 16, tutored by Andy Hillenburg.[4] He began competing in the World of Outlaws Sprint Car Series in 1995; he went full-time in the series in 2005,[5] winning the series' Rookie of the Year title.[6] He ran the full season again in 2008 for Roth Motorsports.[7] Stewart also competed in 360ci sprint car competition; in 2007 he was champion of the Northwest Sprint Challenge Speedweek,[7] and he ran several seasons in the American Sprint Car Series, winning the ASCS national touring title in 2009,[8] and then again in 2011 by a single point over Johnny Herrera.[9] He won the Knoxville 360 Nationals five times;[10] won the Canadian Sprint Car Nationals three times, tied for the most wins in the event with Steve Poirier.[11] Stewart was named 360 Sprint Car Driver of the Year in 2009,[12] and again in 2011,[13] by the National Sprint Car Hall of Fame & Museum.[14]
Stewart joined the newly-formed Larson Marks Racing, later known as Kyle Larson Racing, for the 2014 season.[15] He drove for the team through the end of 2018, winning 35 feature events over multiple series,[16] including the 2015 Kings Royal at Eldora Speedway, one of sprint car racing's most prestigious events.[17][18] His best World of Outlaws points finish came that year, when he finished second in the standings to Donny Schatz.[19] In 2016 he won the off-season Winter Heat Sprint Car Showdown championship at Cocopah Speedway.[20]
Stewart joined CJB Motorsports for the 2019 World of Outlaws season, replacing David Gravel;[21] he won the series's special event at Nashville's Fairgrounds Speedway,[22] but left the team at the end of the year due to a lack of chemistry.[23]
Stewart considered retiring following the 2019 season, having spent two seasons with growing frustration over a lack of stability and performance.[24]
Choosing to return to competition instead, he signed to run ten races with Roth Motorsports;[25] after these events were cancelled due to the COVID-19 pandemic, Stewart ran the majority of the 2020 World of Outlaws season with the No. 71 team owned by Bernie Stuebgen.[26] He won for the team at Williams Grove Speedway in the track's prestigious Summer Nationals,[27] and then at Lakeside Speedway in October,[28] in the first of two races in which he was substituting for David Gravel, who was competing in NASCAR Gander Outdoors Truck Series events, for Jason Johnson Racing.[29]
At the end of the 2020 season, Stewart announced his retirement from active competition, purchasing his home track, Port City Raceway, to promote races there.[30][31]
^Rittenoure, John (April 23, 2011). "Stewart comes full circle". Tulsa World. Tulsa, OK. Archived from the original on January 21, 2021. Retrieved January 18, 2021.
^"Driver of the Year". Knoxville, IA: National Sprint Car Hall of Fame & Museum. Archived from the original on January 21, 2021. Retrieved January 18, 2021.
