James left Preston for Herbert Chapman's Arsenal in 1929 for £8,750, making his debut against Leeds United on 31 August 1929 two weeks before his 28th birthday. In order to circumvent the maximum wage rules, Arsenal arranged it so that his employment at the club was supplemented by a £250-a-year "sports demonstrator" job at Selfridges, the London department store. James had an unremarkable first season at Arsenal, partly due to the recovery from injuries he had accrued at Preston. However his first season brought the first of what would be six trophies in seven seasons when he played in the 1930 FA Cup Final win against Huddersfield Town, scoring the first in a 2–0 win to give Arsenal their first major trophy.