John Winslow was the great grand-son of Edward Winslow, who had come over on the Mayflower and was to become the governor of the Plymouth Colony.1 John's family (his father was Isaac Winslow) lived at Marshfield, Massachusetts. As a young man, John cast about and held a "few minor positions" presumably of the governmental variety; but John, however, was to find his niche in the provincial army. With the outbreak of the War of the Austrian Succession, 1740-1748, he was a "Captain of the provincials" in the expedition against Cuba. How this ended up and where Winslow was to find himself next: I do not know.2
After the war ended in 1748, Winslow was back at Boston. The Winslow family connections were to lead Governor Shirley to recommend Winslow for an appointment as a commissioned officer in the regular British army; quite a step up for a "colonial." From the DCB we see that Winslow was, thereafter, to spend time at Annapolis Royal as a member of the "Fighting Fortieth"; this was prior to 1751. In 1751, he went off active duty, and, taking half pay, returned to Massachusetts to assist Governor Shirley in the administration of the governor's properties. It was during this time, too, that Winslow represented Marshfield in the Massachusetts legislature (General Court) from 1752-53.
In 1754, to again quote the DCB, Winslow "was promoted major-general of militia [sic] by Shirley and chosen to command a force of 800 men which was sent to the Kennebec ..." Thus it was, at Kennebec (a river in present day State of Maine), in response to the rumour that the French were about to seize the carrying place between the Chaudiere and the Kennebec3, that Winslow saw to the building of two forts at places which we know today as Augusta and Winslow, Maine.
The success of the Kennebec Expedition was to add considerably to Winslow's reputation; and, soon thereafter, Governor Shirley was to confide in him that he was pushing his fellow colonial governors to be more active in dealing with the French who were insisting they owed lands in the Ohio Valley and at the Isthmus of Chignecto. "These French need to be pushed back with some military might." Shirley was looking forward to a meeting with his fellow governors and thought he might be in a better position to convince them of an attack plan, if, he, with Winslow's help, could put a Massachusetts' army together before he went off to meet with them. The governors were to meet early in the spring of 1755, so, through the winter, Winslow was charged by Shirley to form an army of New Englanders, to get them outfitted and drilled, and ready for service. During the early part of 1755, Winslow was to muster some 2,000 men at Boston; a feat, incidently, which paid tribute to Winslow's popularity with the ordinary man. They were standing by, when, on April 14th, Shirley met with his fellow governors (Dinwiddle of Virginia; Dobbs, North Carolina; Morris, Pennsylvania; Sharpe, Maryland; and Delancy, New York) at Alexandria on the Potomac (known in history as the Council of Alexandria). In the result there was a resolution to attack the French -- notwithstanding that the two countries were at peace -- at four points, all at once: the English general, Braddock and his regulars, who were then in America, were to attack Fort Duquesne (Pittsburgh); Governor Shirley, Fort Niagara; Colonel William Johnson, Crown Point; and Colonel Robert Monckton, Acadia.
To answer the question as to why the 29 year old Monckton was picked over the 52 year old Winslow to lead up the expedition to Acadia would require a study, a study into the relationship that England had with her colonies, and, in particular, the feelings of the upper class in old England -- of which the upper end of the English army mainly consisted -- towards the democratically inspired leaders of New England. Monckton, however, was not unfamiliar with Nova Scotia; and, indeed, was stationed at Nova Scotia since 1752, and in particular, was, for approximately a year (1752/1753), the commander of the English fort, Fort Lawrence, just opposite the objective, Fort Beausejour. Monckton, too, after all, though but 29, was an experienced regular army officer who had seen action in Europe at both Dettington (1743) and Fontenoy (1745). The appointment of Monckton to lead the New England force not only served the army mores of the time; but, also, the political ones, as Monckton, before coming out to Halifax in 1752, as a newly minted lieutenant-colonel, had occupied his "family seat" in parliament. So, it was, that Colonel Monckton was chosen to go to Acadia to lead a "provincial" force to attack Fort Beausejour. He was assisted in this endeavour by two officers, each in charge of a division of 1,000 men: Colonel George Scott, another regular army officer; and, of course, Colonel John Winslow.
I deal with the taking of Fort Beausejour in our larger story and touch upon, at certain points, the interaction of Winslow and Monckton. While it would appear that Monckton and Winslow had no liking for one another, they did, however (more to the credit of Winslow then to Monckton) get on with one another. Winslow was conscious of his duties to his king, in the person of Governor Shirley, and he helpfully and obediently followed his superior officer.4
With the early fall of Fort Beausejour in June of 1755 (the taking of Fort Beausejour was the only English military objective, of the four, met that year) there was, thereafter, to be an excess of English troops at the isthmus. These troops were bought and paid for, so to speak; and Governor Lawrence determined he now had the wherewithal to follow through on a plan that had long been brewing. In August of 1755, Winslow, with most of his division, at the special request of Governor Lawrence at Halifax, was to travel down from the Isthmus to Minas. There, as the officer in charge, Winslow then proceeded to oversee the deportation of the Acadians at Grand Pre; or, more generally, the Minas area of Acadia.5 For him, as he writes in his journal, this business was a "very disagreeable to my natural make and temper." Winslow's involvement in the Acadian deportation is woven into our larger story.
After carrying out his orders to round up and put the Acadians onto the transports, and after seeing the transports off with their human cargoes; Winslow made his way to Halifax; and, thereafter, sailed with his troops back to Boston. In 1757, with the The Seven Years War now formally started, Winslow was once again involved in a job, one he was particularly good at, of getting a provincial army together. Winslow was with those who attacked the French near Crown Point (upstate New York). That expedition, as were most all the English ones in 1757, due to the ineptitude the English general in charge of American operations, Lord Loudoun, accomplished little.6
It appears that after his military activities in 1757, Winslow, at the age of 53, determined to quit the army (the experiences with both Monckton and Loudoun had to be bitter ones for him) and involve himself in Massachusetts politics full time. Winslow was to serve in the Massachusetts legislature (as he had in 1752-53) as the representative for Marshfield during 1757-1758, and, then again, during 1761-1765. In 1762, Winslow was made Chief Justice of the Court of Common Pleas in Plymouth County.7 Having moved in his later years to Hingham, he died there in 1774.
 See Winsor's Memorial History of Boston (1882), vol 2., p. 551.
 I do not believe John was involved in the First Siege of Louisbourg, though there were two Winslows at Louisbourg: Samuel and William. Samuel was to die there of an undetermined sickness on Sept 7th, 1745. [Louisbourg Journals (New York: Soc. of Colonial Wars, 1932) pp. 140-1.]
 Winslow himself outlined his involvement in a letter to Lord Halifax dated June 27th, 1755; and, as set out in Winslow's Journal, NSHS#4, pp. 178-80. Parkman, in Montcalm and Wolfe (vol. 1) at p. 175, outlines the Kennebec Expedition of 1754.
 Hart described John Winslow as a person remarkable "for his urbanity of manner, kind heartiness and genial qualities ..." (Fall of New France: 1755-1760, at p.159.)
 The Minas area of Acadia included Grand Pre and areas north-west of Grand Pre, an area covering off the farm lands as continue to exist, up through the communities of present day Port Williams, Canning and Blomindon. (See map) Other military officers were to deal with the other areas of Acadia, in 1755: Murray at Piziquid, Handfield at Annapolis Royal and Monckton at Chignecto.
 Lord Loudoun, over the vigorous objections of both Governor Shirley and Colonel Winslow, wanted to mix the militia, or the "provincials," in with the regulars; and, of course, the works under regular army officers. The argument was that the colonial army would operate much better as separate units with its own officers. Loudoun would have none of it. Lord Loudoun, incidently, has been described as "a disgustingly avaricious character." [See von Ruville in his biography on Pitt (London: Heinemann, 1907), vol. 2, p. 168.]
 The Life of Thomas Pichon, "The Spy of Beausejour" by Webster (Halifax: PANS, Spec. pub., 1937), p. 158.