Born in Saint Helena, Bailey's father was a soldier, and the family returned to England in 1857, settling at Bargate (near West Row), Suffolk.
He was elected as the pit's checkweighman, and also became active in the South Yorkshire Miners' Association (SYMA).
[1] Bailey was a founder of the Derbyshire Miners' Association, a split from the SYMA, and represented it on the Trades Union Congress in 1883, 1887 and 1889.
In 1884, he supported a strike at Norwood Colliery, and was fired, forcing him to take work as an insurance agent.
That year, Bailey was invited to become the full-time agent and general secretary of the Nottinghamshire Miners' Association.