Chesson was born in Far Hills, New Jersey, and grew up on a horse farm in Bedminster, New Jersey, where he developed early experience with go-karts and motorbikes. He made his professional racing debut in sprint cars in 1998. From 2000 to 2003 he was a regular competitor in the World of Outlaws winged sprint car series, one of the most competitive and demanding dirt track circuits in North America. His performances on the sprint car scene established him as a skilled car-control specialist before his abrupt switch to open-wheel pavement racing.
In 2004, Chesson made a sudden shift in direction and entered the IRL's Infiniti Pro Series — the primary feeder category for IndyCar — without prior single-seater experience on paved oval tracks. The transition proved immediately successful: he won three races and finished fourth in the overall series standings, a remarkable result considering he missed three races during the season. The achievement drew widespread notice, demonstrating that elite car-control skills from dirt sprint car racing could translate rapidly to the paved open-wheel environment.
Chesson was announced as the driver for Hemelgarn Racing's IndyCar Series entry for 2006, with new backing from NBA star Carmelo Anthony. The team was branded "Carmelo Hemelgarn Racing," and the deal was arranged through Simmons-Abramson Marketing — a firm co-founded by rock musician Gene Simmons and entertainment industry executive Richard Abramson — which had become the IRL's new marketing partner. The unusual pairing of motorsport, basketball celebrity, and rock music business generated notable publicity for the partnership.
Chesson started the first four races of the 2006 season. At the Indianapolis 500, he and teammate Jeff Bucknum made contact on the second lap of the race and both finished in the final two positions. During the final day of qualifying at Indianapolis, Chesson had a tattoo of the 2006 Indianapolis 500 logo applied in public at the Speedway, an act that attracted media coverage in itself.
Following the collapse of his Hemelgarn arrangement, Chesson did not return to IndyCar until the end of the 2007 season. In another deal arranged by Simmons-Abramson, he joined Roth Racing as a second driver alongside team owner and driver Marty Roth, with both entries sponsored by fashion label Dussault Apparel. Chesson made his 2007 debut at the season finale at Chicagoland Speedway. Mechanical difficulties sidelined him for more than one hundred laps and he finished nineteenth.
Chesson's career illustrated both the possibilities and the limitations facing sprint car specialists who crossed over into IndyCar competition. His rapid mastery of the Infiniti Pro Series demonstrated genuine adaptability, but consistent IndyCar results proved elusive amid team instability and the unconventional commercial arrangements that funded his opportunities. His journey from the World of Outlaws to the Indianapolis 500 within the space of two years remained one of the more striking career transitions in American open-wheel racing of the mid-2000s.
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