Carroll Shelby’s dominance in the world of international sports car racing was in full force in late 1963 when he sent the first of his Cooper Monaco-based King Cobra sports racers into battle in the popular—and lucrative—USAC and USRRC “Fall Series” for purpose-built racers, the precursor of the history-making Canadian-American Challenge Cup Series that would open in 1966. Based on the Cooper Monaco, the King Cobra won its first time out at Washington’s Kent Raceway with Bob Holbert at the wheel, but the competition in the no-holds-barred professional racing series was advancing at such a spectacular pace that the concept was already obsolete by 1964. Already at full capacity fielding his existing Ford- backed racing efforts, Shelby turned to old friend Alejandro de Tomaso to produce an all-new racer for the Can-Am that would be the most advanced of its kind. A native of Argentina, de Tomaso was born into wealth and showed early promise managing his family’s considerable land holdings, becoming chief superintendent of all their estancias before reaching 20 years of age. He began racing in 1951 in a prewar Bugatti of long-forgotten provenance, and by 1955 had moved to Italy to race full time. He drove mainly OSCAs, both as an independent and for the Maserati brothers, who had sold the company bearing their name to Modena industrialist Adolfo Orsi and returned to their home town of Bologna to establish the OSCA operation. It was a fruitful partnership that produced excellent results, most notably at Sebring and Le Mans in 1958, leading de Tomaso to open his own company, DeTomaso Automobili, in Modena in 1959. A string of various Formula racers ensued, followed by his first production road car, the Vallelunga, which featured de Tomaso’s signature advanced lightweight “spine” chassis. By then it was clear that de Tomaso was a bold innovator, and it was this characteristic above all that drew Shelby’s attention in his quest for a winning Shelby Can-Am machine. With Shelby providing financing and de Tomaso the engineering, the project also involved Peter Brock as designer and Carrozzeria Fantuzzi as fabricator. A key part of the arrangement was that de Tomaso would develop a 7.0L version of Ford’s 289 CI small-block V-8 to take on Chevrolet’s new all-aluminum big-block. However, just as the prototype was nearing completion, the project was terminated; displeased that de Tomaso had failed to produce the promised engine and enticed by Ford to lead its GT40 program, Shelby walked away, leaving the entire works to de Tomaso, who showed the completed car at the November 1965 Turin Auto Salon. Because the car, originally named P70, was designed for the free-wheeling Can-Am, its Brock-designed bodywork disqualified it from the more stringently regulated FIA Group 7 class. The solution was the one and only DeTomaso Sport 5000 Roadster. Presented in the March 1966 Road & Track as the first of 10 intended for production with the prospect of another 40 to meet homologation requirements, it was instead the only one produced, only briefly seen in competition before vanishing for decades. Like the P70, the Sport 5000 used de Tomaso’s backbone chassis design employing a mid-mounted, race-tuned Ford 289 CI V-8 as a stressed chassis member. Equipped with four Weber downdraft carburetors, aluminum heads and special camshaft, cam timing and ignition, this aggressively tuned small-block delivered 475 HP at 7,300 RPM to a Colotti- inspired 5-speed transaxle. The Sport 5000’s body also closely resembled Brock’s original design. A higher windshield and full doors brought it into compliance with FIA Group 7 homologation rules, but it otherwise remained faithful to Brock’s beautifully functional design, even to the extent of using his large driver-adjusted rear spoiler that promised unprecedented downforce and road adhesion. The Sport 5000 made a single appearance in competition on July 17, 1966, when DeTomaso test and development driver Roberto Bussinello drove it in the Mugello 500km race. Leaping off the grid, Bussinello easily pulled away from the Ferrari 250 LM beside him at the head of the pack, but trouble struck early, and the Sport 5000 retired from the race. It was subsequently entered in the 1967 12 hours of Sebring and the Monza 1000km, but it was a no show in both cases. In fact, it never again turned a wheel in anger, instead disappearing into the recesses of the DeTomaso factory in Modena for nearly 40 years. It resurfaced following Alejandro de Tomaso’s passing in 2004. In 2005, the Sport 5000 was sold from de Tomaso’s estate to a Belgian collector who then drove it in several historic racing events before selling it to a U.S.-based collector. The lone DeTomaso Sport 5000 remains unrestored, fully functional and in incredibly original condition, retaining the original 289/475 HP small-block and DeTomaso-built Colotti-style gearbox. It also still features the original Fantuzzi-crafted, Brock-designed body, paint and livery. This unique and fascinating automobile, the product of a star- crossed collaboration between four of automotive history’s giants, is offered with extensive historical documentation and period photographs.