Webb Jay was born Dallas County, Iowa. He was a racing driver competing in his White Steamer nicknamed Whistling Billy, due to the unsual high pitched exhaust sound. Whistling Billy used an underslung chassis and covering a mile at 74.07 mph. The White Steam cars were produced by the White Sewing Machine Company of Cleveland, Ohio.
In 1905 there was a National Automobile Racing Championship with designated races and points. It was probably the first such championship in America. The main rivals for the title were Webb Jay and Barney Oldfield in the Peerless Green Dragon.
On the 26 June at Empire City, Yonkers, New York, Webb won the first heat but in the final came second to Louis Chevrolet. At the same event Louis Chevrolet beat Barney Oldfield in the special two-thousand dollar match race arranged as a big feature.
A week later at Morris Park, Bronx, New York, Webb Jay and Louis Chevrolet were the only starters, however at the last moment the Louis' engine broke and Jay took the race by default.
In August at Grosse Pointe, Detroit, Michigan, he won the Ten-mile Open on the 7th. The following day, Barney Oldfield had an almost miraculous escape when Dan Wurgis crashed into him during the first mile of the five-mile open event. The race had to be abandoned. In stead Jay and Burman drove another five-mile race which Jay won.
Once again a week later (14th August) they were at the Glenville Driving Track in Cleveland, Ohio for5 laps of the 1.0-mile track. Charles “Charley” Burman won in his Peerless with Herbert Lytle second in a Pope-Toledo followed by Jay in Whistling Billy.
Webb Jay's racing career came to an end in 1906 when the "White Steamer" he was driving plunged into a pond in the infield of the Buffalo NY track where he was competing, and he came close to drowning.
After months in the hospital, he decided to take up safe pursuits. At first, he became the "White Steamer" dealer in Chicago, the city where his brother Frank was selling the "Stanley Steamer."
In 1908 He and his brother, Frank Jay, deceided to built their own steam car. This was marketed in Chicago as the "Webb Jay," or just "the Jay." At $4,000, it was an expensive car, powered by a 2-cylinder 30-horsepower compound engine. It was available as a 5-passenger touring car. The "Webb Jay Motor Company" offered the car only in 1908. Thereafter, the brothers returned to dealing in autos of other manufacturers. Frank Jay became Vice President of the Stanley Motor Carriage Company. Webb Jay invented the vacuum tank concept which was purchased by Stewart Warner. This transaction, it was said at the time, "brought him sufficient of this world's goods to enable him to retire from the industry."