James’s career began at Kirkcaldy’s second-division Raith Rovers in 1922, but his goalscoring abilities soon attracted the attention of English league clubs and he was signed by Preston North End three seasons later. In 1928 he was a member of the ‘Wembley wizards’ Scotland team that beat England 5-1. Anxious to cash in on his fame, James more or less forced his own transfer to Arsenal, with whom he won the league four times. He was a prolific spender and made Arsenal circumvent the maximum wage rule of £8 a week by signing for additional employment as a ‘sports demonstrator’ at Selfridge’s department store. Part of the ‘Scotland’s Dream Team’ commission, this work appears based on a photograph of James in the capacity of reserve team coach at Arsenal after the Second World War.