Perhaps the most humiliating FA Cup result in Chesterfield's football history was the 1-0 defeat suffered by the old Town club at little Ripley Town in 1912. Masterminding the Ripley performance that day was their Secretary/Manager, J.J. Caffrey, and it was to Caffrey that Chesterfield's directors turned when looking for a successor to the disgraced Tom Callaghan in 1919.

Joseph James McCaffrey was born in Birmingham in 1870 and the family moved to Derbyshire when Jim was in his teens. Somewhere along the line the family dropped the "Mac" and Jim Caffrey, as he was known, emerged from the mines and went into business as a seed and flour merchant in Ripley, becoming a respected local tradesman. His interest in football saw him serve as secretary to the Derbyshire Senior League as well as Ripley's senior club.

Apart from Caffrey's undoubted organisational ability, the respect held for him was as important to a Chesterfield board attempting to restore the credibility lost when the infant club was slung out of the FA Cup in 1919. He was appointed from January 1st 1920 at a salary of £300 per annum. This was still the era of municipal football and Caffrey's official title was that of "Sports Manager" to the town council, who paid one third of his salary in recognition of the fact that his duties included running the municipal swimming baths and boating lake.

Caffrey's side maintained the momentum built up after Callaghan's dismissal and became Midland League champions in May 1920. While Harry Cropper, the club's visionary chairman, promoted the formation of the Third Division (North), Caffrey made sure the team was up to the task of playing in it. This he did, in an unassuming way. The club's advancement would bring about Caffrey's departure, though.

In the run-up to the return to the Football League significant hurdles had to be overcome, and a clique of new investors in the board room sought to scapegoat Caffrey for many of these, despite the fact that the directors themselves made every decision of any great consequence. Some felt that the club needed a higher-profile manager and, in the summer of 1920, they sought to make Caffrey's position untenable by forcing his resignation from the council side of his job. Caffrey got round this by making his council job a summertime one only, but his detractors wouldn't give up, and he was finally forced to quit on April 8th 1922, when the club decided to make the manager's position a full-time, year-round one. Weighing everything up, Caffrey no doubt opted for the greater security offered as the council's Sports Manager and Hackney Carriage Inspector.