 Chesson akaita kutanga kwake kwenyanzvi mumotokari dzomumhanyi muna 1998 uye kubva muna 2000 kusvika muna 2003 akanga ari wenguva dzose muWorld of Outlaws winged sprint car series. Muna 2004 akangoerekana asarudza kuchinja basa rake uye akatyaira mu IRLs Infiniti Pro Series achikunda makwikwi matatu uye achipedza wechina mumakwikwi emakwikwi pasinei nekushayikwa kwemakwikwi matatu. Akaziviswa semutyairi wemotokari yeHemelgarn Racing muIndyCar Series muna 2006 nerutsigiro rutsva kubva kuNBA nyeredzi Carmelo Anthony. Kubatana kwacho kwakanzi Carmelo Hemelgarn Racing. Chibvumirano chacho chakaperekedzwa nomubatsiri mutsva wokutengeserana weIRL, Simmons-Abramson Marketing, yakaumbwa nenhetembo yedombo Gene Simmons uye nyanzvi yeindasitiri yevaraidzo Richard Abramson. Chesson akatanga makwikwi mana ekutanga emwaka, wekupedzisira ari Indianapolis 500, kwaakabatana naye Jeff Bucknum mumutambo wechipiri uye akapedza mumatunhu maviri ekupedzisira. Chesson ane zviratidzo zvakawanda, kusanganisira chimwe che2006 Indianapolis 500chiratidzo chaakanga ashandisa paruzhinji paSpeedway mukati mezuva rokupedzisira rokugadzirira. Kubva pakapera chibvumirano chake naHemelgarn, Chesson haana kudzokera kuIndycar Series kusvika pakupera kwemwaka wa2007 apo, mune imwe Simmons Abramson brokered deal, Chesson akaziviswa semutyairi wechipiri weRoth Racing padivi pemuridzi wechikwata Marty Roth nemotokari mbiri dzakatsigirwa nemhando yemafashoni Dussault Apparel. Akaita kutanga kwake muna 2007 mumakwikwi ekupedzisira emwaka kuChicagoland Speedway uye akapedza ari 19th mushure mekunge mechanical gremlins amubvisa kunze kwemazana zana. 