Carroll Shelby (1923–2012) was a maverick whose brilliance and tenacity were matched by talent, guts, and good fortune. He strung together an impressive trail of victories that included three first-place finishes at the 24 Hours of Le Mans: one as a driver racing in his trademark bib overalls—a holdover from the early days when he would go directly from his chicken-farm job to the tracks—and two as a designer whose Ford GT40s decimated their Ferrari rivals in the mid-1960s. As humble as he was shrewd—once, after a car magazine photographed his single prototype, he painted the car a different color before showing it to other magazines, creating the impression that he had two cars—Shelby often attributed his success to the engineers, designers, and drivers with whom he surrounded himself. The CSX 2000 shown here was the first Cobra built by his company, Shelby American. It begot the fierce and formidable 289 and 427 roadsters and was followed by the coveted Daytona Coupe and the 1965 Shelby Mustang that popularized his name. The auto world will be poorer without Ol’ Shel’, but his cars remain to remind us of this bigger-than-life character from a singular era in automotive history.