Manufactured by Smith and Mabley of New York City, the first Simplex hit the streets in 1904. This impressive luxury touring car was powered by a 35 hp four-cylinder engine with a double chain drive chassis. Although sales were decent, the company went bankrupt in 1907, and it was soon taken over by a wealthy customer and textile manufacturer, Herman Broessel. Once again, the company prospered, garnering a reputation for producing very fast cars modeled after the finest of Europe, per Broessel's passion for racing. But when he died in 1912, his sons took over, and sales quickly plummeted. Within a year, the brothers sold to a New York investment consortium anchored by a member of the Goodrich Tire family. Simplex was quickly merged with the newly acquired Crane Motor Car Company to yield Crane-Simplex in 1915.

Where the Simplex was fast and brawny, Henry Middleton Crane was known for his sophisticated, elegant and extremely expensive cars, built to order for the ultra-wealthy. A bare chassis sold for a whopping $8,000. Crane's reputation was bolstered by his award-winning work in the engineering of speedboats. The company's new management wanted to create a six-cylinder model to compete with Rolls Royce's Silver Ghost, and retained Crane to create it for them. Expanding on Crane's Model 4, the new Crane-Simplex Model 5 featured a gigantic 563.7 cubic inch engine cast in blocks of three cylinders, claiming about 110 bhp at 1800 rpm. The car's longitudinal leaf spring suspension was considered cutting edge for its time, and provided a relatively smooth ride, though both rear wheel and transmission brakes weren't enough to confidently provide a sure stop for its hulking 6000 pounds. When introduced, the chassis was priced at around $5,000, but went up in price about $1000 for each year of its production. In total, 121 models were produced before the company was acquired in 1916, and production of the Model 5 was suspended.

One of the most notable of the Crane-Simplexes is Jay's one-of-a-kind Model 5 Holbrook Skiff. Holbrook, who was known for his sober limousine-type carriages, drew design cues from Crane's love of speedboats. Among the car's nautical elements are mid-carriage entry, portholes in the cowl, a propeller on the spare tire carrier, and mahogany rub rails. The car's first owner, J.H. Baxter bought it off the floor of the 1916 Palace Hotel Auto Show in San Francisco for $10,000, and it later spent many years in the personal collection of casino owner William F. Harrah.