As America began to emerge from the Great Depression and tensions flared in Europe, Cadillac was hard at work producing what would become the future rubric for automotive design. In 1938, the entry-level Series 60 Special was introduced, replacing the Series 61. Designed by Harley Earl protégé Bill Mitchell and powered by a 346 cubic inch V8 that was introduced in 1937, the 135hp mill gave the Sixty Special a better power-to-weight ratio than its chief rival, the Packard Super Eight (which also cost $700 more to buy).

Mitchell's new design did away with the running boards, creating a more enveloping front end with 'catwalks' extending between the front fenders and the nose of the car—a look that would evolve into the '41 Series 62 with its fully enveloped headlights. While the exterior design remained largely unchanged from '38-'40, the '39 models had a redesigned dashboard, "Controlled-Action Ride", and rubber rear fender protectors.

The offered Sixty Special has been in the same family for 56 years. Purchased new from Dickson Motors, Ltd of Winnipeg, Canada by a couple hailing from nearby Manitoba, the Caddy was sparingly driven and stored from the beginning of WWII until the vendor's uncle acquired the car in 1955. Driven very little and carefully garaged in Toronto, the car was given to the Southern California based vendor by his uncle about ten years ago. It has been carefully maintained and remained lovingly presented and unrestored, showing only 80,000 miles on the clock. With little opportunity to drive the car, the vendor has decided to finally let it leave the family it has been with for the past half a century.