Vivian Hugh Smith was a descendent of the banking family which founded Smith's Bank at Nottingham. He worked for the merchant banking firm of Morgan Grenfell & Co. and became a director of many important companies but his career in the City was most notable for his term of no fewer than sixty years as a Director and later as Governor of the Royal Exchange Assurance. He was created a Baron in 1938. Although he had always loved horses it was only late in life with the acquisition of Tusmore Park near Bicester that he could indulge his passion, acquiring a string of successful steeplechasers. Other notable artists of the day painted his portrait including Sir Herbert James Gunn, R.A. and Sir Alfred James Munnings, P.R.A. who portrayed him on horseback in hunting pink.
This was probably one of the earliest commissions Orpen carried out after his return from the Peace Conference in Paris in 1919. It may well date to September 1919 when, according to an unpublished letter from Orpen in Paris to William Marchant of the Goupil Gallery, dated July 1919 (Tate Gallery Archive), 'I'm going back [to London] for three weeks early in September to paint two portraits. (I ain't got any money).' The plea of poverty and the need for money was understandable at this time considering that Orpen had been surviving, providing for a family, household and schooling on a Major's pay for the previous two years or so, when he was employed in the capacity of Official War Artist.