Living in Preston, Bailey came to prominence in the 1860s as an advocate of the establishment of a national trade union federation.
He attended the United Kingdom Alliance of Organised Trades conference in 1867, representing the Preston and Blackburn branches of the newly founded Amalgamated Society of Journeymen Tailors (ASJT).
[1] He was elected as vice-president of the ASJT and, later in 1867, was arrested along with the other leaders of the union, on a charge of conspiracy to impoverish business owners during a strike.
At the congress, he read a paper by George Potter which made a forceful case for trade unionism, and has often been quoted as if it were his own words.
[7][8] In 1883, he was one of three British delegates to the International Trades Union Congress in Paris, alongside Henry Broadhurst and John Burnett.