One day James Tilghman, Secretary of the Land Office under the Proprietaries, called at the Trimble store and made some purchases. Young Trimble, who waited upon him, also made out his bill, and the great gentleman was so much pleased with his writing and business style that he at once took measures to secure his services in his department. Thus James Trimble at the age of fifteen years became an apprenticed clerk in the Land Office. The endorsement upon the archives of the Board of War and the Council of Safety indicates that James Trimble was subordinate clerk in the State Council as early as 1775, and when Colonel Timothy Matlack became the first Secretary of the Commonwealth, March 6, 1777, James Trimble became Deputy Secretary, and so continued down to Thursday, January 14, 1837. Pending some difficulties with the Supreme Executive Council in regard to his accounts of his money trust, Colonel Matlack resigned his position as Secretary, and March 25, 1783, General John Armstrong, Jr., was commissioned in his stead. General Armstrong was elected a member of Congress in 1787, and November 7 of that year Charles Biddle became Secretary. He served in that office until January 19, 1791, when Alexander James Dallas, Esq., was commissioned by Governor Thomas Mifflin the first secretary of the Commonwealth, under the Constitution of 1790. On March 12, 1791, the very day the Governor approved the Act of Assembly providing for a Deputy Secretary, Mr. Dallas appointed James Trimble, who had served continuously under his several predecessors, to be Deputy Secretary, and the appointment was approved by the Governor. Secretary Dallas resigned his commission December 2, 1801, when Thomas McKean Thompson succeeded him. Nathaniel B. Boileau became Secretary of the Commonwealth, December 20, 1808, and remained through the three terms of Governor Simon Snyder, when he was succeeded by Thomas Sergeant, December 16, 1817; he resigned July 6, 1819, when Samuel B. Ingham was commissioned; Andrew Gregg took up the reins of office December 19, 1820, serving three years, when Molton C. Rogers became Secretary; he resigned January 2, 1826, to be succeeded by Isaac G. Barnhard, who served less than two years, when Calvin Blythe was commissioned November 28, 1827; Samuel McKean was commissioned December 16, 1829, and was succeeded by James Findley who served until December 15, 1835, when Thomas H. Burrowes became Secretary of the Commonwealth, and in all this time, and with these fifteen changes in the office of Secretary, a commission and dedimus issued regularly every three years to James Trimble as Deputy Secretary of the Commonwealth. His records are models of neatness, his papers elaborately endorsed, and filed with great care, so that in those days of tallow candles, when he was wont to enter his office at night, he could, without striking a light, lay his hands on any paper he wished.