The Rise and Fall of Sheriff Winslow

Paper Presented to the Carleton Historical Society

28 April, 1995.

In memory of Charlotte Winslow


A few years ago Sandy Briggs, a childhood friend, asked if I had ever seen the Queen. Without thinking I replied that though I had never laid eyes on Her Majesty, I had once had supper with Charlotte Winslow.

Like the queen, Miss Winslow really was special. Though she had many Victorian virtues – thrift, industry, hospitality, and what Mrs. Homer always refers to as “pluck” – in other respects Charlotte was an original. In my own circle of acquaintence, there is no one at all similar to Charlotte Winslow, and I suspect that would be true for most of us.

Anyone who lives a long life will be known to different people in different ways. The Charlotte I became acquainted with, in the last twenty years of her life, was the historian. Many people will suppose Miss Winslow's approach to history began and ended with her father's family. I never found this to be so, but she did have an ample measure of what one New Brunswick historian called “well-regulated family pride.” What most impressed me about Charlotte's view of local history was that it rose above the merely sentimental. Too often practitioners of local history think that it is about nostalgia; but Charlotte was interested in the hard facts, the more the better. Look, for example, at her superbly researched paper for this society in 1980 on Douglas Winslow on the Russian Front at the end of World War I.

My last correspondence with Miss Winslow, which continued nearly to the time of her death, was on the early career of the man whom we always call Sheriff Winslow, the first (and third) High Sheriff of Carleton County, and I know she would approve of a remembrance of her which took the form of a paper on her great-grandfather.

• • • • •

Sheriff Winslow was born in 1793 and died in 1859. That is, he lived only 66 years; but in political terms Sheriff Winslow lived too long for his own peace of mind. We get a hint of this in Winslow's gravestone in Christ Church cemetery, the inscription on which surely one of the most remarkable in Carleton County — tells us that he was “respected even by his enemies.” We get much more of the same in a 1200-word obituary which his son inserted in the Winslow newspaper — the Woodstock Journal — in 1859. Here the late sheriff's conduct and character were defended at length, in terms such as the following:

"Undaunted in danger, impulsive of spirit, ever ready at the call of duty, fearless of consequences, immovable by either threat or bribe, frank, simple-minded and upright, a staunch friend, a generous enemy, he reminded one less of the men of the present day than of the gallant and highminded gentlemen of a departed age… Probably many of his opponents, many of those whose acts embittered his latter years, as little understood him as he understood them, and where there is lack of sympathy there is little respect and no love."

So far as I can tell, the obituarist's extravagantly defensive — indeed, extravagantly political — depiction of Sheriff Winslow was pretty accurate. My paper tonight attempts to explain why Sheriff Winslow's declining years were soured by the bitterness proclaimed in those unfading words on his gravestone. I do so not so much by talking about what he did during his quarter century as sheriff but by describing how his career as sheriff opened and how it closed.

Consider first the name: John Francis Wentworth Winslow. Sherrif Winslow was named after the Loyalist John Wentworth, sometime governor of New Hampshire and latterly governor of Nova Scotia; he was likewise named after Wentworth's wife Frances, sometime mistress of Queen Victoria's father the Duke of Kent, when he was stationed at Halifax during the Napoleonic Wars. Consider also his parentage: Went Winslow was born on the Kingsclear estate of his father Edward Winslow, one of the most brilliant of New Brunswick's founders, but also one of the governing elite's poorest members in financial terms; he had 10 children. Consider the year of his birth: 1793. Went Winslow grew up at a time when the New Brunswick economy was utterly stagnant, when the only good jobs were government appointments, and all of these were filled by long-lived Loyalists of his father's generation. What was the son of an impoverished gentleman, coming to maturity in the first decade of the 19th century to do? The dilemma confronting Went Winslow, as with so many other sons of the Loyalist elite, was that they risked becoming lesser men than their fathers. Their fathers had come to maturity in a world turned upside down by the American Revolution, but in that general calamity there were many opportunities. Fate had given their fathers a dashing military career in the Revolution, taken them to London, put them on familiar terms with lords and generals, and then given them a new province to govern. The creation of New Brunswick in 1784 was a make-work project for the Loyalist elite. But what were their sons to do? The fathers — like Edward Winslow — had attended Harvard, but the shipwreck of the Revolution meant that there was no money to send the sons such as Wentworth Winslow. The fathers had, relatively early in life, been appointed to govern a province, but by Went Winslow's days, all appointments were taken. The son of an elite gentlemen, born as was Winslow in 1793, faced the cruel knowledge, that he would probably never attain the status in the world of his own impoverished father. The second Loyalist generation was a generation in concious decline.

Went Winslow and his family felt this dilemma acutely. Their letters on this subject are numerous and almost pathetic. What was to be done with young Went? The obvious option for the son of a soldier, born at the beginning of the long Napoleonic Wars, was to join the army. This Winslow did at the age of 16. He was soon serving in Upper Canada, as a lieutenant in the 41st regiment. Here, perhaps characteristically, he got into some sort of terrible quarrel with another officer. I wouldn't be surprised if what turned it into a scandal was a duel.1. One of the most striking features of the Maritimes from the coming of the Loyalists to the 1820s was the prevelance of duelling. I suspect that young Maritime men were so sensitive in matters of honour for the very reason that they were so insecure. If like young Winslow, you knew in your heart that, while your father was a gentleman, your own status in the eyes of the world was doubtful, then you were more apt to imagine slights to your honour. In any event, as a result of this messy quarrel with another officer, both were forced to resign their commissions.

Now Winslow was really in trouble. No doubt it had taken all of his old father's influence, and perhaps money, to get his son a commission; and the son had thrown it away. Yet it gives an insight into young Winslow's character that, instead of accepting disgrace bitterly, he attached himself to another regiment, the 104th, that mostly NB-recruited regiment which played such an important role in Upper Canada during the War of 1812. But Winslow's status in the 104th was merely that of a Volunteer. A Volunteer was a soldier with the rank of a private but one who, because a gentleman, was allowed to mess with the officers. In this ambiguous role Winslow acquitted himself so well that in 1819, some years after he left the service, he was allowed retrospectively the rank of lieutnenant and put on half pay.

So here was young Winslow, aged 26, out of work, his father now dead, and utterly without prospects. He soon compounded his problem through involvement in a famous scrape that got him charged with being an accessory to murder. When George Street fatally shot George Wetmore in a duel in 1821, it was Wentworth Winslow who was acting as the dead man's second. The three survivors at once took what was almost the standard for duellists by fleeing to Robbinston (Maine), just across the St. Croix river from St. Andrews, but not before a proclamation of Hue and Cry was issued authorizing all citizens to hunt them down and arrest them on sight. The trio remained in Maine for quite a time until finally agreeing to return and stand trial for murder. However I cannot see that Winslow himself was actually tried. Street was tried, of course, and acquitted, after Judge Saunders virtually told the jury to do so.

By this time Winslow — young no longer — was an undereducated, unemployed man without solid prospects. To Montreal he went for a position in the Northwest Company, but he was too late. Then he tried working a land grant in the vicinity of Perth (Upper Canada), but as one of his sisters noted, he was suited to anything better than farming. By 1828 times were so hard for him that he sold out his half pay for a lump sum. Not until 1832, when he was nearly 40, did Winslow land a proper job. The influence of his friends was still strong enough to secure his appointment as sheriff in the newly created County of Carleton. Under the rules by which the patronage game was played prior to the rise of political parties, such appointments were always arranged for hangers-on of the governing elite. Appointment was not brought about by merit. Everything was influence and connexion.

The new county came into being officially on 1 January 1833 — not 1832 as we always think — and Sheriff Winslow was soon established in a house at Court House Corner, as it was called, in Upper Woodstock. In 1839 he described his residence as “beautifully situated, and possessing most of the conveniences which a country gentleman could desire.” It was here in Upper Woodstock that Winslow performed, for a quarter century, the multifarious responsibilities of sheriff in a county which, for most of his tenure, stretched from Eel River to the Quebec border. What did a sheriff do? Few positions are now so little understood in comparison to their importance. The sheriff's principal duty was to supervise deputies and constables in serving the writs that began a lawsuit. This sounds not especially burdensome, but in a time when anyone sued who failed to give sureties for appearance at trial would be held in gaol, this was a troublesome business. Then, once the lawsuit was over and the plaintiff had a judgment, it was up to the sheriff to seize and sell enough of the property to satisfy the judgment and, of course, the sheriff's own fees. This fee part was important. Like most government appointees prior to quite recent times, the office carried no salary. The income of sheriff, deputies and constables, like that of the justice of the peace, was derived entirely from fees. What else did sheriffs do? They ran elections; prisoners in the gaol were theoretically their responsibility; they summoned jurors, and normally it was they who called and chaired meetings on political questions. The sheriff's duties were certainly hazardous both legally and physically. He and his constables were always being sued for seizing the wrong cow or the wrong logs, and were frequently assaulted by debtors who did not want to be served with their writs. Finally, the sheriff was charged with apprehending criminals, though this came into play only in the more unusual cases. For Sheriff Winslow the most famous criminal proceeding of his career was apprehension of the 139 indicted Catholic rioters after the Battle of Woodstock in 1847. It was the sheriff's duty to round them up and hold them pending trial or pre-trial release.This would have been no easy thing at any time, but the situation was compounded by the fact that the Carleton County gaol had burnt just before the riot. As it is not the purpose to discuss the details of Winslow's private career, I leave for another time a more substantial discussion of Winslow and the riot aftermath — particularly his controversial decision to exclude all Catholics from the rioters trial jury on the grounds that only Protestants would be unbiased. I will quote briefly, however, from his description of the pains he took to apprehend one of the riot ringleaders:

To Sheriff Winslow, the most important event in his career was probably his ouster from office. According to his son, it was this that triggered his early death; and it is this event which accounts for the defiant mention of enemies on his tombstone. I don't know whether Charlotte Winslow knew the details of her great-grandfather's downfall but, had one asked her who was the great enemy of all Winslows in the 19th century, she would certainly have known the answer. Sheriff Winslow's career was sacrificed to the political dictates of Charles Connell.

The intense emnity between the Winslows and the Connells, and the rival Woodstock newspapers which they controlled, probably began the day Carleton County was created. Before 1852, when the county council form of local government came into operation, a county's internal affairs were ordered by a body known as the General Sessions of the Peace. The General sessions consisted of all of the JPs in the county meeting together twice yearly to appoint parish officers, set the poor rates, audit accounts, pay scholl masters, and so on. These JPs were themselves appointed by the Executive Council in Fredericton. In other words, before county councils, there was no elected local government in New Brunswick outside of Saint John; all local affairs were in the hands of the appointed JPs. In the early days of Carleton County, especially, this group consisted mainly of Dibblees, Bedells and Ketchums, who advised the perennial clerk of the peace, Smedes Wetmore. With this group of Tory appointees, Sheriff Winslow was very close. The Connells, on the other hand, were shopkeepers by trade, reformers in politics, and Methodists in religion. In their struggle for political power, they made little headway in the Tory-dominated General Sessions of the Peace, but they had remarkable success in attracting enough votes from the upriver parishes to win election to the House of Assembly in Fredericton. The first of the Connells was Jeremiah, Charles' elder half-brother. In February 1838 Jeremiah rose in his place in the Legislature to complain that Sheriff Winslow had refused to give a proper accounting of money passing through his hands. Significantly, the Tory dominated Carleton County General Sessions had refused to demand this accounting from Winslow, so Connell was demanding it in the legislature. I interpret this attack on the sheriff as having little to do with accounting for money; rather it was part of a political struggle between the elected representative of the people and the JPs who controlled the Sessions. It was the Connells versus the Lower Woodstock gentlemen, and Winslow just happened to be in the way. However, this attack on Winslow by Jeremiah Connell in 1838 is useful background to a more successful Connell attack on the sheriff 20 years later.

In those twenty years the entire face of New Brunswick politics changed. In 1841 the British government conceded responsible government to the province — that is, a system in which the provincial executive was answerable to the elected representatives of the people — the system of government we have today. The so-called struggle for responsible government produced two political alignments in the province — Conservatives, who resisted RG on the grounds that they themselves might lose power, and reformers (Liberals), who thought that the government should be run by the people who won elections. The appointed JPs who dominated Carleton County's local government and, of course, Sheriff Winslow, were of the Tory group; the Connell brothers, and their supporters in the Baptist-dominated parishes of central Carleton County, were among the most extreme of the Liberals. The moment of destiny for New Brunswick came in 1854, when the Liberals won the provincial general election and formed the first one-party government in the province's history. Nicknamed Smashers, because they set about destroying the vestiges of Toryism, Charles Fisher's Liberals abolished the remaining priveleges of the Church of England, secularized King's College into the University of New Brunswick, created general public schooling, brought in the secret ballot, and dismissed long-tenured office holders. Among the chief of Premier Fisher's supporters was his brother-in-law, Charles Connell.

That removing Sheriff Winslow from office was one of the principal goals of Charles Connell's life was clear even before the great change of government. In the spring of 1854, while the Liberals were still a minority in the Legislature, Connell had introduced a sensational bill to make the position of sheriff of Carleton County elective. It came as no great surprise, therefore, when, in 1856, the new Liberal government dismissed Winslow as Sheriff and replaced him with Samuel Dickinson. When Winslow's sympathizers introduced a resolution into the legislature condemning the government's action, Charles Connell and the county's other Liberal stood in their place to accuse Winslow of derelection of duty and exacting illegal fees, charges which — Winslow was keen to point out — they would never repeat outside the legislature. This, for Winslow was the very worst: not merely to be dismissed, but to be accused of dishonesty in circumstances where the accusers were not accountable.

So public life seemed over for the first high sheriff of Carleton County, but fate gave one more turn of the wheel. One of the new Liberal governments reform measures was legislated prohibition of liquor. This measure proved so unpopular that the Lietenant-Governor was able to turn them out of office and install a Conservative party government. In 1857 this Tory cabinet excused Sheriff Dickinson from further performance of duties and appointed in his place John Frances Wentworth Winslow. Thereby the first high sheriff of Carleton County became the third high sheriff of Carleton County. The next year, however, the Fisher-Connell faction came back to power and was again superseded, this time by the more acceptable Jenkins Dibblee. Winslow's loss of office was recognized as one of the most important political events of the day. He was a sort of test case on the meaning of Responsible Government, and his fate proved that all public positions were now to be regarded as political, to be held by the friends of the government of the day. In vain did Winslow send off his petition to Queen Victoria. Within a year of his second dismissal, he was dead.

“Sheriff Winslow”, read part of his obituary, “belonged to a class of men who seem to be fast disappearing in this province. He was the son of (a Loyalist and) to this class belonged Mr. Winslow in spirit. He was possessed of all their reverance for the throne, of all their respect for the ancient institutions of their country, and of the generosity of spirit and high sense of honour which were among the worthiest of their characteristics.”

In writing these words, the sheriff's son came close to admitting the proposition with which this talk began: that by his death in 1859 Winslow had already lived too long, politically speaking. His career had begun as a classic instance of the old, pre-Responsible-Government-style connextional politics. He was named sheriff of Carleton County in 1832 primarily because he was his father's son. But the courtly, high minded sheriff also exemplified all the virtues of the old regime: a man who might think himself neutral between Orangemen and Catholics because he disdained both groups. But if Winslow's career was the creation of one sort of politics — the politics of dynastic influence — then his downfall a quarter-century later was the product of a new politics — the politics of political partizanship. The sheriff may have been, as his gravestone proclaims, respected even by his enemies, but his enemies had triumphed.


1.  The reason Winslow was asked to resign his commission is the day after arriving at Ft. George, on March 29, 1812, from Fort Erie, he was in the officers mess drinking some wine with other fellow officers and it had reached a point of "being over-served". The senior officer present was Lt. Edmund Cartwright, also of the 41st Regiment, and he had served in the Nova Scotia Fencibles with young (18 years old) Mr. Winslow.

Some harsh words were spoken and Mr. Winslow got up and slugged Cartwright while he was still sitting in his chair! This caused a brawl among the other officers.

When General Brock heard of the incident, he asked for both officer's resignation and received them. Cartwright's father, also Edmund, used some political clout to get his son reinstated in late July but the correspondence I have come across clearly show that other officers blamed Cartwright and they were upset that Winslow was the one that had to pay for it.

Within 3 - 4 months, Cartwright exchanged into the Canadian Voltiguers, more than likely to escape animosity among his fellow officers. Cartwright died in Rheims, France in September 1819.

— Tod Molesworth, Marana, AZ