In 1938 Cadillac introduced its second-generation V-16. The new engine featured a 135-degree V design with L-cylinder heads and a nine-main-bearing crankshaft. It provided horsepower and torque comparable to the marque’s earlier V-16s, while weighing a remarkable 250 pounds less and being less costly to build. The new V-16 engine, classified by Cadillac as the Series 90, was mounted in a chassis of the same 141 1/4-innche wheelbase as the eight-cylinder Series 75, enabling the two series to share Fleetwood bodies. Twelve Series 90 body styles were catalogued for 1938 and 1939, all with beautiful styling directed by Cadillac’s Chief Designer Bill Mitchell. For 1938, Cadillac produced a total of 315 examples of their new V-16.

This 1938 Cadillac V-16 was ordered new through Cadillac Auto Company of Boston, Massachusetts, the New England distributor for Cadillac at the time. One of 10 V-16 Convertible Coupes built that year, the car was finished in Chinchilla Gray (20126) with Royal whitewall tires and an undocumented special order Fleetwood interior (SO 3049). Factory accessories included a master radio and aerial, as well as a heater/defroster. It was delivered to Sutcliffe Storage Co. of Brighton, Massachusetts, likely utilized as overflow inventory space for nearby Newton Centre Garage, Inc., the authorized Cadillac, LaSalle, and Oldsmobile dealership which operated out of a compact downtown lot.

By the 1990s the Cadillac had made its way to California, and it is believed to have been refinished to current presentation around this period. In 2005 the Cadillac joined Aaron Weiss’s respected collection, later earning a National First Prize Award at the CCCA annual meeting in 2007, after which it was rarely shown. It was subsequently acquired in March 2023 by Charles Lyford of Washington state, and then by The Groendyke Collection in October 2025, where it has proudly represented the second generation of Cadillac V-16 engine design.

By the mid-1930s, Cadillac had convincingly won the decade's “cylinder wars.” While rivals like Lincoln, Packard, Pierce-Arrow, and Rolls-Royce offered nothing higher than a V-12 during this era, Cadillac produced not only a V-12 (through 1937) but also a V-16, which remained in production through 1940. This 1938 Cadillac V-16 stands as a magnificent testament to pre-war automotive engineering and luxury, and as one of only 10 such Convertible Coupes made that year, highlights the model’s exclusivity as well. Nicely presented today, it is a CCCA Full Classic that would make a for a wonderful addition to any collection.