1999 Indian Chief Vintage Limited Edition

FROM THE DICK SHAPPY COLLECTION: The 1999 Indian Limited Edition Chief

In 1897, George M. Hendee, an accomplished bicycle racer from Massachusetts, founded the Hendee Manufacturing Company to produce bikes. They were initially branded Silver King and Silver Queen until the name American Indian was adopted and then shortened to Indian in 1898. In 1900, Hendee teamed up with Oscar Hedstrom from Sweden to develop single-cylinder motorcycle prototypes in Middletown, CT. Together, they opened the first factory in Springfield, MA in 1901 to create the first American motorcycle company where they would be produced until 1953. They hired the Aurora Automatic Machinery Company to manufacture their engines in 1901, which they did under license until 1907 when they would go on to produce Thor motorcycles.

By 1910, Indian was the world's largest motorcycle manufacturer. The iconic Scout (1920) and Chief (1922) became extremely popular when they were introduced, but production shifted to military bikes during both World Wars, significantly impacting consumer market share. Despite innovation, including four-cylinder models and the acquisition of Ace, the company struggled post-WWII, leading to its closure in 1953. However, the name would continue. The British owner of Royal Enfield used the Indian name on imported bikes from 1955 until around 1960. In 1963, enthusiast Floyd Clymer acquired the trademark and sold rebadged British bikes. In 1998, a group formed the Indian Motorcycle Company of America, and this 1999 Indian Chief Limited Edition represents the first year of the brand's reintroduction. Sometimes referred to as "Gilroy Indians" as they were manufactured in Gilroy, California, they marked a significant comeback with classic styling, powerful S&S engines, and a limited production of 1,100. The blend of vintage styling with modern reliability, distinctive paint, full-skirted fenders, and unique badging made these bikes highly collectible.

The Indian Motorcycle Company produced motorcycles until 2003, selling to London-based Stellican Ltd., which relaunched production. In 2011, Polaris Industries purchased the brand and revitalized it with modern engineering and classic styling. Today, Indian offers contemporary cruisers, baggers, and performance bikes, continuing its legacy with models like the Chief, Scout, and FTR, maintaining its place as a major motorcycle brand. In 2025, Polaris sold Indian Motorcycle to private equity firm Carolwood LP, aiming for greater independence. Every iteration of Indian has brought something unique, carrying the torch George Hendee lit in 1897.


YEAR: 1999

MAKE: Indian Motorcycle Company of America

MODEL: Chief Limited Edition

VIN #: 5CDCNB511XG001020

LIMITED EDITION: 1,020 of 1,100

ENGINE: S&S Super Stock 88 cu. in. 1,442 cc. 75 HP V-twin

CARBURETOR: S&S Super E

MILEAGE: 21,675

BRAKES: Single disc brakes at both ends with polished billet four-piston calipers

TRANSMISSION: 5-speed with a belt drive to the rear wheel

EXHAUST: 2-into-1 chrome fishtail with Indian logo

FRAME: Steel with a 36-degree rake

TANK: Teardrop 4.7-gallon featuring a large analog speedometer and dual fuel-filler caps

FENDERS: Full-skirted (valanced)

WHEELS: 16 in. 60-spoke chrome wire

HANDLEBARS: Wide, pulled back (roughly 36 in. wide)

SUSPENSION: 41 mm telescopic front forks with chrome shrouds and a hidden rear monoshock mounted to a box-section swingarm

PAINT: Brown & cream with silver pinstriping

SEAT: Corbin fringed leather solo seat

FEATURES: VIN# badging, a "warbonnet" (Native American head with headdress) marker light, chrome headlight nacelle, chrome accents, teardrop headlight, passenger pegs