Started racing in 1906 on the 1 mile beach course at Ventnor, NJ. Driving a Buick 22 he finished second.
In 1907 he won the hillclimb at Giant's Despair, Wilkes Barre, PA. in a Chadwick 50 and finished third in his Chadwick 60 in the 1 mile straight drag at Wildwood, NJ.
In 1907 Lee Chadwick, working with J.T. Nicholls, developed the idea of pressurizing an engine's carburetor to increase volumetric efficiency. Initially, they used an 8-inch diameter, single-stage centrifugal compressor driven at five times engine speed by a belt from the flywheel. It worked well beyond their expectations, but like any gearhead worth their salt, they craved even more power. To this end, they decided to install a three-stage blower driven at six times engine speed. The new, improved blower utilized three impellers, each with twelve blades, all of 10-inch diameter but of different widths. This compressor provided a three-stage compression, which fed the carburetor with even more pressurized air.
In May of 1908, Chadwick entered his car in the Great Despair hill climb in Pennsylvania and won. It's believed that this was the first competitive event in which a blown car was entered, never mind the winner. Over the next two years, the car dominated lots of events, the most notable being the 200-mile road race at Fairmont Park in 1910.
Driving the supercharged Chadwick in 1908, he won again at Giant's Despair. He also won at Dead Horse Hill, Sport Hill Cleveland, and Skippack Hill PA. and finished second in his Chadwick in the 1 mile straight drag at Wildwood, NJ., then winning the touring car class in a Matheson. In November of that year he raced in the inaugural 'American Grand Prize' in a supercharged Chadwick.
In 1909 he raced in the Vanderbilt Cup but went out on the first lap when his crankshaft broke. He also took part in a 200 mile race in Philadelphia dropping out after 3 laps with valve trouble.
In 1910 he was part of the Benz Team in the American Grand Prize.
In 1913 he entered the Indy 500 in a Mason. the Mason was actually the first Duesenberg. The racing fraternity initially referred to them as the Dutch farmers from Iowa but with their 350-cubic-inch, four-cylinder engine developing a then-impressive 100 horsepower, they soon became players in the big league. Jules Goux won that year in a Peugeot with Haupt finishing a creditable 9th.
As part of the works Duesenberg team he returned to Indy in 1914 and in 1915 as well as competing in other Championship races.