Indian's Chiefs and Fours were at the head of the company's catalog, but many would argue it was the Scout that gave Indian its soul. Like the early Chiefs, the first Scout in 1920 was the handiwork of designer Charles Franklin. Both models marked Indian's casting off of its bicycle roots and the evolution to a proper modern motorcycle. The middleweight Scout was originally powered by 37ci (600cc) V-twin running a three-speed gearbox; it was capable of 60 mph. A hit from the start, the bike gained a quick reputation for reliability: "You can't wear out an Indian Scout," went a catchphrase of the day. The motor would grow to 45 inches (750cc) and lead to the 101 Scout, still regarded by many as the finest Indian ever, "...a machine that shoots away like the wind on an open stretch, yet rides as comfortably as a Pullman," read the brochure copy.

A misstep came in 1932 when the same basic frame was used for the Scouts, Chiefs and Fours, leading to a heavy and ponderous-feeling Scout. A more sporting chassis arrived in 1934 and it was a Sport Scout that won the inaugural Daytona 200-mile race in 1937. Hobday's circa-1938 Sport Scout wears Indian's "World's Fair" paint scheme and appears to have been retrofitted with the type 741 engine from an Indian military bike, though internal specification is unknown.