Thomas Jackson Oakley (November 10, 1783 – May 11, 1857) was a New York attorney, politician, and judge.

[2] He graduated from Yale College in 1801, studied law with attorney Philo Ruggles in Poughkeepsie, and was admitted to the bar in 1804.

[2] Among his notable cases, Oakley and Thomas Addis Emmet represented Aaron Ogden in the landmark case Gibbons v. Ogden, which the United States Supreme Court ultimately resolved in favor of Gibbons, who was represented by Daniel Webster and William Wirt.

[6] They were the parents of a son:,[7] Robert Williams Oakley, a Union College graduate, attorney, and militia officer who died unmarried in 1832.

[6] After the death of his first wife Oakley married Matilda Cruger (1809–1891);[8] the daughter of Henry Cruger, who had the unique distinction of serving as both a member of Parliament (1774–1780; 1784–1790) and as a New York State Senator (1792–1796)[5] Thomas and Matilda were the parents of five children, three daughters and two sons.