The introduction of the 300 SL was a hugely important moment for Mercedes-Benz and served to further cement the company’s position as the market leader in race-bred performance automobiles. Well ahead of its time, the 300 SL utilized an innovative space-frame chassis coupled with a highly advanced, fuel-injected engine, the first of its kind fitted to a production car. The 300 SL was conceived by Mercedes-Benz importer Max Hoffman, who believed that a road-legal version of Mercedes-Benz’s successful W194 racer would be profitable and that the unique style and performance of such a car would resonate with his American clients.

Looking to expand upon the success with the “Gullwing” coupe, Hoffman believed that a convertible version of the 300 SL would also sell quite well, and the convertible roadster was introduced in 1957. Of course, as the 300 SL would lose its top, engineers had to reinforce and modify the space-frame chassis to fit conventionally hinged doors. Through lowering the height of the chassis, this simultaneously allowed for greater ease of entry. Cosmetic changes were minor and included a smaller grille opening and dual chrome strips along the side sills, giving the car a more streamlined and glamorous look. At the rear, the spare tire was repositioned below the trunk floor, necessitating a smaller fuel tank but also maintaining reasonable luggage space. These revisions added some 250 lb to the total weight of the car, mostly due to the convertible top.

Looking to keep the speed and performance of the coupe, Mercedes-Benz fitted the sportier NSL engine of the coupe to all roadsters as standard equipment. This made the roadster capable of top speeds that ranged from 133 to 155 mph, depending on the final drive ratio specified. However, the stunning performance and design of the 300 SL roadster did not come cheap at a list price of $11,000 (though worth every penny). Ownership of a 300 SL implied an exquisite taste in engineering and aesthetics, and it was the ultimate automotive statement. Naturally, many found homes in the garages of celebrities, racing drivers, and other successful individuals with an appreciation for fine cars.

This 300 SL roadster was acquired new by Jim Gilmore Jr. of Kalamazoo, Michigan, on 8 March 1958 from Gezon Motor Sales in neighboring Grand Rapids. The Gilmore family had a successful department store in Michigan, and Jim Jr. developed a diverse business empire that included a broadcasting corporation and car dealerships. A well-known figure in Indy racing, Gilmore was a true racing enthusiast and sponsored successful teams from 1967 until 1990. Legendary driver A.J. Foyt joined the Gilmore team in 1973, and in 1977, after Foyt’s fourth Indianapolis 500 win, they partnered to create Gilmore Foyt Racing and enjoyed a close friendship for many years.

Jim Gilmore Jr. ordered his 300 SL roadster to stand out from the rest. Many were finished in subtle colors, but this example was ordered in striking Strawberry Red Metallic. Only approximately 30 roadsters were finished in this unusual color. With its ivory hardtop and cream interior, it surely is one of the most distinctive 300 SLs. Gilmore enjoyed the car until his passing in 2001, when his daughter, Ruth Langs, inherited the Mercedes-Benz. Ruth and her husband maintained the roadster for another six years and during this time had it regularly serviced, with many worn-out components such as rubber seals and exhaust components replaced as needed. A new coat of Strawberry Red Metallic paint was applied around this time.

In 2009 the Gilmore family sold the roadster to a lady enthusiast in California, and at this time it had traveled just 21,985 miles. Its second owner enjoyed the car for the last decade, including participating in the 2010 Mille Miglia Santa Barbara Rally. Today it has just 25,700 miles and is a fantastically original 300 SL roadster, which has clearly benefitted from careful ownership resulting in its well-preserved condition.

Always enthusiast-owned, this 300 SL has been maintained and repaired as needed over the years but has never been restored. Included are the original owner’s manuals, tool kit, jack, original Bill of Sale, original title with folio from Gezon Motor Sales, hardtop, and service documents. The Mercedes-Benz data card confirms its engine remains original as expected, considering its documented history and low mileage. With stunning original specification and exceptional ownership history, this highly original roadster stands out from its peers.