He was briefly the party's secretary, in late 1898, and was the ISRP's first candidate for election, standing unsuccessfully in 1899 in the North ward for Dublin Corporation.
Stewart was again serving as its secretary, and Connolly objected to his management of the finances; in particular, prioritising paying bar bills ahead of rent and printing costs.
The matter was largely resolved in Connolly's favour within a fortnight, and a motion that Stewart be expelled fell by only a single vote.
Connolly attempted to persuade the others to rejoin, but not Stewart, who he believed had hoped to move the party to reformism.
[2] That year, he became the election agent for the United Irish League, and in this post, opposed the workers in the Dublin Lock-out, spreading rumours that organiser Larkin was being paid by the Orange Order.