At the age of seven he passed his entrance examinations at Yale University, but did not enter until 1763; he graduated in 1767, studied law there, and in 1771–1773 was a tutor (taking part in teaching and supervising the undergraduates).
[1] While studying at Yale, he contributed to ten essays in 1769 and 1770, titled "The Meddler", imitating The Spectator, to the Boston Chronicle, and in 1770 similar essays, signed " The Correspondent" to The Connecticut Journal and New Haven Post Boy.
[1] While a tutor he wrote his first satire in verse, The Progress of Dulness (1772–1773), an attack in three poems on educational methods of his time.
[3] After the Revolutionary War, Trumbull was a staunch Federalist, and with the "Hartford Wits" David Humphreys, Joel Barlow and Lemuel Hopkins, wrote "The Anarchiad", a poem directed against the enemies of a firm central government.
[5] Prior to moving, he was one of the 31 founding charter members of the Connecticut Historical Society and was elected its first President.