Complex sentence: He led two rebellions against the Canadian government and its first post-Confederation Prime Minister, Sir John A. Macdonald; the Red River Rebellion of 1869--1870 and the North-West Rebellion of 1885 which ended in his trial.
Split into simpler sentences: He led two resistance movements against the Canadian government and its first post-Confederation Prime Minister, Sir John A. Macdonald. The first resistance was the Red River Rebellion of 1869--1870 and the second was the North-West Rebellion of 1885 which ended in his trial.