[5] In 1872, Benson competed in the 3 mile race in the University sports, in which he finished in a dead heat in 15 minutes 44 seconds with Cambridge's Edward Montague Hawtrey,[6] whose brother John played for Old Etonians in the 1879 FA Cup Final.
In the final, played at Kennington Oval on 14 March 1874 against a team from the Royal Engineers, the university ran out as 2–0 winners, with goals from Charles Mackarness and Frederick Patton.
[12] In October 1874, Benson was sent to Boston to join the family mercantile business but returned to England after the sudden death of his father in January 1875.
This partnership was only short lived, and was declared bankrupt in June 1875[13] following the failure of many creditors after the financial crash of 1873, which had been masked by accounting irregularities.
Benson amassed a substantial personal fortune by identifying Chicago and the mid-west as growth areas, following the 1873 crash, selling out profitably as the economy recovered.
[6] By the early 1880s, Benson had started to build up his collection of Italian pictures, with the purchase of several paintings in 1884 from the art dealer Martin Colnaghi, including Portrait of a Collector by Mario Basaiti, Madonna and Child, attributed to Bastiano Mainardi, and A Triumphal Procession with Prisoners by Andrea Schiavone.
[1] During the First World War, the banking operations were virtually suspended, enabling Benson to write about economic policy and act as an unofficial city advisor.
As a result, in 1924 he brought his three sons into the business, and sold his collection of Chinese porcelain by auction at Christie's in order to raise funds.
[21] The couple had five children:[22] From 1902 to 1927, Benson and his family lived at Buckhurst Park, Withyham in (East) Sussex which he rented on a 25-year lease from Gilbert Sackville, Earl De La Warr.
During his time at Buckhurst, Benson made considerable changes to the house,[1] engaging architect Edwin Lutyens to add an extensive wing.