Oliver Wolcott Jr. was born in Litchfield, Connecticut, on January 11, 1760, earning degrees from Yale University and Litchfield Law School.

Wolcott gained his first professional experience in the Continental Army during the Revolutionary War, performing duties as his father's aide-de-camp and then as quartermaster (1779-1881).Initially leaving the Army to practice law (1781), Wolcott quickly moved on to the financial sector, working in his home state of Connecticut as a member of the Committee of the Pay-table (1782-1788). That committee became the Office of the Comptroller of Public Accounts in 1788, and Wolcott remained in its employ, serving until 1789 as its first comptroller. Wolcott then went to work on the national level, becoming the first auditor of the federal treasury in 1789. Two years later, he rose to the position of comptroller of the Treasury Department, and in 1795, he began his service as secretary of the treasury in the administration of President George Washington (1795-1800). Wolcott left the cabinet following accusations of improprieties by political enemies and served briefly as judge for the Second Circuit Court (1801-1802). In 1802, he established Oliver Wolcott & Company, an import-export firm, and remained in that business until 1810 despite his firm's dissolution in 1805. Continuing in finance as a member of the board of directors of the Bank of the United States (1810-1811), Wolcott established the Bank of America in 1811, working there until 1814.

He re-entered public service in 1817 upon winning the election for governor of Connecticut, serving for ten consecutive one-year terms through 1826. He was also a delegate to the Connecticut state constitutional convention in 1818. Oliver Wolcott died in New York City on June 1, 1833.