Walter Owen Bentley, known primarily as W.O., began his career as a British railway engineering apprentice with a penchant for racing motorcycles. In 1912, Bentley and his brother H.M. formed a company named Bentley and Bentley to sell French DFP cars. Unsatisfied with the car’s performance, W.O. employed aluminum, then a revolutionary material, to redesign their pistons, and soon broke several records on the race track. These lightweight pistons were to become one of the secret ingredients of Bentley’s future success, but the advent of the Great War delayed his plans. Accepting a government commission to power the Sopwith Camel, Bentley designed two aircraft engines, which were credited with Allied dominance of the air. In his later years, Bentley admitted that no other accomplishment had given him greater pride.

The roaring twenties was Bentley’s decade of glory and great adventure, and the earsplitting roar of his cars became synonymous with the devil-may-care attitude of that era. After the war, W.O. founded his own company, Bentley Motors, to live his dream of building a car that would satisfy his own demanding expectations. The first complete Bentley was hand-built and high tech, with a four-cylinder, three-liter engine; Bentley was the first to utilize four valves per cylinder and dual spark plugs. Despite rave reviews, Bentley created two more prototypes before selling his first Bentley to wealthy and influential playboy, Noel van Raalte, the first of the notorious “Bentley Boys.”

Young and unknown, Bentley turned to the racetrack to prove the car’s mettle, placing fourth at the inaugural 24-hour race at LeMans, where his cars would go on to create many records and legends. At one point, on a bet, Bentley Boy and diamond heir Woolf Barnato raced the car against a train from Cannes to Calais and won! Barnato dug Bentley out of hock in 1926, buying up most of the stock and becoming the company’s managing director. He also drove the famous Six Speed Racer to win three victories at LeMans, a record which stands to this day.

Eventually, Barnato announced that Bentley would retire from racing, as expenses were quite high, and the public was getting a one-sided impression of the car. The Wall Street Crash greatly affected business, as Bentley had just launched its eight liter (one of which Jay owns) in direct competition with its archrival Rolls-Royce. Despite attempts to save the company, Bentley and Barnato were forced to sell to an anonymous holding company in 1931. According to legend, Bentley unhappily found out that the unknown company was actually Rolls-Royce several days later when his wife overheard that tidbit at a cocktail party.