Rupert Jiffkins, third eldest of eleven children of William and Clara Jiffkins was born on 20th October 1881 at East Maitland, NSW. His parents emigrated from the United Kingdom around 1876 and William found employment in the NSW prison system. Due to the nature of his employment the family moved around the state eventually settling in Annandale, an inner suburb of Sydney.
Nothing further is known of Rupert’s childhood and teenage years, however by school age the family lived in Quirindi and several years later moved to Sydney. (1)

In 1901, at age 20, Rupert married Violet Walsh at St Stephens Church, Newtown. (2)

Shortly after he moved to France where he found employment at the Serpollet factory where he claimed he was involved with their entry in the Boulogne Sur Mur road races. Later he moved to England where he claimed to have worked for both Daimler and Rolls Royce. The latter claim is dubious as Rolls and Royce did not amalgamate until 1905. (3)

By 1904 he was in the United States, now using the name Jeffkins and claimed that he participated in the early races on Ormond Beach in Florida in a Rolls Royce. An exhaustive check of Ormond Beach records shows that the first and only appearance of a Rolls Royce at that venue was in 1907 when the driving was shared between R.A.McCready and C.E. Hutton. If he was at that venue with a Rolls Royce it may have been as a crew member or perhaps a riding mechanic. He also claimed to have competed in the Milwaukee 24hour race, but again nothing has been found to confirm this. (4)

1910 finds Jeffkins living in Webster City, Iowa, where he was employed by motor dealers Hanson and Tyler as the Manager of their Service Department. Newspaper articles describe him as a ‘long term auto racing promoter’. On 4th July the first ever auto racing program was held on the Webster City Driving Park – the cities premier horse racing venue. The auto races proved popular with more than 2000 spectators lining the half mile oval. The second race on the program was a ten miler between Ray Stockslayer in a Cole 30, Bert Barrett driving a Mitchell and Jeffkins in a stripped Overland. Jeffkins won the race with a two lap lead. The feature race was a ten mile event between Jeffkins, R.Austin and Bert Barnett. Jeffkins was billed as a daredevil who exhibited cleverness and daring as he piloted the Overland. Austin was driving an Anhut Six and Barnett a stripped Overland 25. On his seventeenth lap Jeffkins had a large lead when his carburettor malfunctioned – he stopped, removed the tool kit, repaired the problem and resumed the race to finish in second place. Later in the program, Jeffkins drove a five mile exhibition which he covered in just over six minutes. This was exceedingly fast for the half mile and averaged 55mph which prompted the city newspaper to comment on his skills – comparing him to Barney Oldfield. (5)

On 5th September 1910, Jeffkins promoted a motor race program on the Marion track in Cedar Rapids. This track was described as the best horse racing venue in Iowa and featured six foot banked turns. Heavy publicity preceding the meeting attracted between four and five thousand spectators but the meeting was described as ‘tame’. Heavy rain the day before had turned the roads around Cedar Rapids into a quagmire preventing many of the competing cars from distant places being able to make the trip through the mud leaving the fields rather depleted and processional. The program consisted of twelve races for cars and two for motorcycles. Jeffkins only competed in one race – a 20 mile event – but a blown tyre at the 15 mile mark put him out of the running. (6)

One month later, on 5th October, Jeffkins appeared at the inaugural motor races at the Carroll Fairgrounds in Iowa. Rain again on the morning of the event depleted entries across the ten race program and only about 1000 spectators attended. Jeffkins in an Overland was only listed to compete in one event, but was forced to retire with mechanical problems midway through his race. (7)