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Livingston's marriage to Governor Fitz-John Winthrop's daughter was no doubt instrumental in his taking up residence in New London and subsequently receiving a commission in the Connecticut militia. He had served previously in the New York militia. When not occupied by military affairs, Livingston was a merchant. In 1701 he owned the sloop Mary, in partnership with his brother-in-law, Samuel Vetch. They became involved in the illegal but profitable trade with Canada, a trade which soon came to the attention of colonial authorities. As late as 1706 it was rumoured that Livingston was still involved in such nefarious activities. During 1706-7 Livingston represented New London as a deputy to the general assembly. He also speculated in Indian lands during this period.
Livingston's restless nature suited him well for the life of a soldier. Known as "the Mohauk," he acquired great influence among the New England Indians, especially the Five Nations. His ability to control the Indians marked him as a valuable asset to colonial commanders. In August 1704 after the outbreak of Queen Anne's War, he commanded a company of "Volunteers English & Indians to reinforce the Frontiers." A month later Livingston had his "first adventure" in "a publick capassety" when his father-in-law appointed him "to visit the 5 Nations" with commissioners appointed by Governor Dudley of Massachusetts. Though the commissioners gained assurances that the Five Nations would "take up the Hatchet," this support was not utilized at the time.

Livingston was serving as a Connecticut officer on the Massachusetts frontier early in 1705 when he learned that Dudley was sending a delegation to Quebec to negotiate an exchange of prisoners. Livingston volunteered and was sent overland from Albany to begin negotiations. Although "the Expense and Industry of our Commissioners in this Affair was very great," release was obtained for only a few of the 117 captives, most notably the Reverend John Williams. Livingston, termed a "very honourable man" by Governor RIGAUD de Vaudreuil, returned to New England in June 1705 with Captain Augustin le Gardeur de Courtemanche, the French governor's agent for the exchange of prisoners, who continued the negotiations with Dudley.

In 1709 Livingston, now a major, prepared to take part in the still-born Vetch expedition against Quebec. A year later he was again with Vetch, this time as commander of a party of Indians which flanked the main body of troops in the successful expedition led by Francis Nicholson against Port-Royal (Annapolis Royal, N.S.) With Auger de Subercase's surrender in October 1710, a council of war resolved that Livingston, accompanied by the Baron de Saint-Castin Ernard-Anselme d'Abbadie, "should go to the Governour of Canada, about the exchange of Captives, and inform him how Matters were" at Annapolis Royal. Livingston was, as Vetch put it, "perhaps the only Brittish subject of any figure or character capable of such extraordinary undertakings." The "Journall" that he kept attests to the arduous nature of this mission, which would have come to an early end had not Saint-Castin intervened to save Livingston from death "in a barbarous manner" at the hands of a distraught Indian. After almost two months' hard travel, Livingston arrived in December 1710 at Quebec where he was received "with all imaginable marks of civillity." His time in Quebec was well spent. While awaiting the arrival from Montreal of Hertel de Rouville and Simon Dupuy, agents whom Vaudreuil was sending to New England to continue the negotiations and "to obtain information through them of the movements of our enemies," Livingston prepared notes for "A View of Canada," an account of the fortifications and troops at Quebec. This was probably the chief purpose of the mission, for a successful expedition against Quebec had long been in Vetch's mind.

Livingston returned to New England late in February 1710/11 and at Vetch's urging prepared to leave for England. It was hoped that his knowledge of Canada could be used to persuade the court to renew plans for a general assault on New France. Stormy weather postponed his trip and word from England that another expedition was under way made it unnecessary. As preparations for the Walker expedition began, Livingston's knowledge of Quebec was utilized by both Admiral Walker and General John Hill. Livingston was questioned by the general "about the situation and works of Quebec, and was thought to give a very good account of it." The failure of Walker to navigate the St Lawrence successfully meant that Livingston's knowledge of Quebec could not be put to use.
Having "a verry great sway amongst them," Livingston, now a colonel, spent the better part of the next year and a half recruiting Iroquois for scouting work around Annapolis Royal and as a result was "considerably out of pockett." The fort was deprived of the officer best able to control the Indians when Livingston left at the end of 1712. He returned to New London where he was granted the right to erect a saw-mill in 1713. He liquidated his holdings there in 1718 and sailed for England where he hoped to recoup the money he had lost in supplying the garrison at Annapolis Royal. His early death denied him the honour of succeeding his father as the second lord of the Livingston manor in New York.

Although he was tied by blood or marriage to some of the most important families in New England, Livingston remains an obscure figure who moved only at the edges of the important events of his time; a figure who appeared to be more at home with the Indians than with his fellow colonials.⁵