After leaving college he returned to
South Carolina, and remained there for some years. He returned to
New Haven, Connecticut and studied law with S.P. Staples, Esq., and began to engage in the practice of law. He took an active part in the political movements opposed to the
Federalist Party in
Connecticut, both as a public speaker and as an editor of the
Connecticut Herald, which he had purchased. He was Clerk of the New Haven County Court. About 1824, he returned to South Carolina, where he practiced law until 1833. Flagg's attachment to his native State was strong, but his devotion to the
Union was stronger, and like his friend,
James L. Petigru, with whom, side by side, he withstood the
nullifiers in 1832, he was true to the last. Designing to educate his children at the North, he then again took up his residence in New Haven, where his home continued till his death. He practiced law until 1842 when he retired. From 1834 to 1839 he was
Mayor of New Haven. ==Personal life==