Union Agitation
In 1889, Fleming helped form a Melbourne lodge of the Knights of Labor in Melbourne, as well as being elected to the Eight Hours Committee.
In September, 1890 Fleming was first elected as a delegate of the Victorian Operative Bootmakers Union to the Trades Hall Council, and later served on the Executive. He supported inter-colonial strikers, female organisation, and agitation for piece work rates as opposed to a minimum wage which the employers were after. Due to declining union membership, Fleming was instrumental in the Trades Hall Council devising union re-organisation, which resulted in a number of unions being brought into existence and many old ones strengthened. Often his support of grass roots initiatives, self-help and the unemployed put him at odds with trade union bureaucrats and Labor politicians such as William Trenwith, who he accused of 'working with blood-sucking capitalists.'
Twelve months later he was elected, unopposed, President of his union for a 6-month term, and for a similar period as President of the Fitzroy branch of the Progressive Political League, the fore-runner of the ALP. Fleming was a supporter of Max Hirsch, author of Democracy versus Socialism.
At a Knights of Labor meeting in 1893, Fleming moved the motion for what was subsequently the first May Day procession in Melbourne. This was the start of a long association between Chummy Fleming and May Day in Melbourne. During the 1930s, when Fleming's anarchist politics was out of favour with the May Day Committee, then controlled by the Communist Party of Australia, Fleming started marching a block ahead with his red flag with Anarchy emblazoned in white, going so slowly the march caught up with him; or sometimes he started back In the ranks and gradually edged to the front.
In 1895, at a large meeting at the Melbourne Town Hall, Fleming and John White moved a motion successfully opposing the Melbourne Lord Mayor, Sir Arthur Snowden, from chairing the meeting because of remarks he had made supporting very low wages. A commentator in Tocsin articulated that it forced words to become deeds and resulted in the introduction of the Factories Legislation.
In 1904 Fleming was expelled from Trades Hall Council for attacks on Labor parliamentarians (disloyalty to Labor). Fleming's continual criticism of Trades Hall bureaucrats and Labor opportunists was echoed by noted Trade Unionist and socialist, Tom Mann.
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