Charles, the son of a prosperous draper in Main Street, was a gifted student at the local classical school in St. Clare’s Hall and later at St. Patrick’s College, Cavan. Following three years of study for the priesthood in Maynooth, he won a seat for the Irish Parliamentary Party in the Leitrim North by-election of 1906. However, he soon became frustrated with the slow rate of progress which the IPP was making at Westminster in its demands for Home Rule for Ireland. When the Liberal Government proposed a very watered-down type of Home Rule, the 26-year-old Dolan called on IPP members to withdraw from London and establish their own parliament in Dublin, which would manage Irish affairs and promote native industries. John Redmond, the leader of the party, failed to respond to this appeal. So Charles resigned from the IPP to recontest the election for the fledgling Sinn Féin organisation, which was advocating similar policies to his own. To promote his campaign, Dolan founded and published the Leitrim Guardian newspaper in Manorhamilton. He lost the election, but then set up the Breffni Boot Company with capital of £5,000 in an attempt to establish a shoe factory in his home town. However, despite his spending more than a year studying the shoe industry in St. Louis, Missouri, USA, the venture never got off the ground. In 1912, Dolan returned to St. Louis where he married Katherine Kenney. They had one daughter, Alice. Charles began to study law soon afterwards. Upon qualifying as a lawyer, he worked mainly as a member of the St. Louis Law Department staff. When he retired as Associate City Counselor in 1960, he was made a freeman of the city.
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