In 1917, Michael Collins was elected to the Sinn Fein executive. During 1917 and 1918, his activities included: creating an intelligence network, organising a national loan to fund a rebellion, creating an assassination squad ("The Twelve Apostles") and an arms-smuggling operation. By 1920, Michael Collins was wanted by the British and had a price of £10,000 stg. on his head.

In 1919, Michael Collins personally, with the help of his friend Harry Boland, another IRB man, went to Lincoln gaol in England to help Eamon de Valera escape. And, during the time de Valera was in America trying to raise money for Sinn Fein, Michael risked his life to visit de Valera's wife Sinead and their children every week with money to keep the family. Michael had a life-long love for older people and for children.