Andrew Oliver built a successful Boston trading business with his brother Peter, dealing in wine, textiles and Atlantic commerce. He entered town government as auditor in 1737, won election to the provincial assembly in 1742 and became Massachusetts's secretary in 1755. Family and political ties connected him closely with Thomas Hutchinson, among a powerful group of royal officials.

Appointed stamp distributor in 1765, Oliver became the immediate target of resistance to the Stamp Act. Protesters hung him in effigy from the Liberty Tree in August and attacked his property. He announced that he would not perform the office, but renewed suspicion brought another public confrontation in December. Under crowd pressure he swore that he would never act as distributor. His own account of the episode describes anonymous demands, newspaper notices and the forced appearance, documenting how resistance could make an imperial appointment unenforceable.

Oliver remained provincial secretary and became lieutenant governor when Hutchinson took the governorship in 1771. The publication in 1773 of private letters written by the two men during the earlier imperial disputes revived hostility. Opponents read their discussion of stronger authority as a threat to colonial liberties. The controversy damaged both officials and further discredited the government. Oliver died in Boston in March 1774, before open war began. His final years exposed the gap between royal office and public acceptance.