Born in Scotland, he first joined the 42nd Regiment of Foot, also known as the "Black Watch," and was present at the British capture of Montreal in 1760, as well as the invasion of Martinique in 1762.
[1] In the summer of 1763, Robertson went with his regiment to relieve Fort Pitt in present-day Pennsylvania, which was under siege by Native American forces during Pontiac's War.
"[1] However, he eventually became entangled in local politics around merchant disputes with the military, and was also accused of leading a campaign against his fellow justice Pierre du Calvet.
[1] In 1779, Robertson was appointed commandant at Fort Osgewatchie, a small British post near present-day Ogdensburg, New York.
[1] On 13 August 1782, General Frederick Haldimand sent Captain Daniel Robertson to the British post at Michilimackinac in the newly expanded Province of Quebec.
[1] Sinclair had started construction of a new fort on Mackinac Island and was accused of extravagance in distributing supplies to maintain British relations with the local Ojibwe and other Native American tribes.
Like his predecessor, however, he quickly found that maintaining relations with Native American allies in the region was expensive and difficult to control.
[5] They had grown accustomed to a certain level of British hospitality, and Robertson felt compelled to distribute gifts to them rather than anger such a large group.
[1] In 1784, Matchekewis returned to the fort on Mackinac Island to collect his annual distribution of supplies and was angered when Robertson refused, denouncing the deceitfulness of the British.
Robertson recommended a location near present-day Thessalon, Ontario to Governor Haldimand and also suggested engaging his son-in-law, Montreal merchant Daniel Sutherland, to supply building materials for a new fort.
[1] He applied unsuccessfully for the position of Indian agent for Michilimackinac, but remained at Mackinac Island until the summer of 1787, when he returned to Montreal.
[1] According to local legend, Captain Daniel Robertson built a small summer house on an overhanging cliff at the southeast corner of Mackinac Island, now called Mission Point.
Robertson was said to have entertained his fellow officers at his summer house, where they enjoyed smoking pipes and cigars, and drinking wine.
[9] However, after a few years, part of the cliff including the summer house collapsed to the base of the rocks, leaving a mass of debris on the beach.
[12] After arriving at Mackinac, Captain Robertson retained them as slaves and wrote that he refused to return them to "a set of Spanish rascals.
[1] On 16 November 1787, Captain Robertson also emancipated his slave Hilaire Lamour as a reward for his "25 years of true and faithful service.
[13] Lamour most likely borrowed money to raise the sum, which meant that Catherine technically became her husband's slave and subject to seizure by his creditors in payment of his debt.