Sheriff Stephen Greenleaf
- westmohney

- Jan 31, 2023
- 12 min read
Updated: Feb 21, 2023
...the Sheriff came to inform me that there was a most violent and virulent paper stuck up upon Liberty Tree... ~ Massachusett Governor Francis Bernard

the office of sheriff
The first keepers of the peace in colonial times were the constables. It seems that most able-bodied men in colonial towns took a turn as constable and many of our relatives held that title. Constables apprehended the law-breakers and enforced local ordinances. As the colonies became more established and populated, the governor in each colony began appointing sheriffs with broadened duties to enforce laws, collect taxes, supervise elections, run the jails, select juries, and manage prisoners.
The man with the most difficult job of keeping the peace in the years prior to the Revolution would have been the Sheriff of Suffolk County. Boston, where most of the action was happening, lay in the County of Suffolk. The man who held that position in those years was our cousin Sheriff Stephen Greenleaf (4C7X). As sheriff in such tumultous times, Stephen had his hands full trying to control increasingly hot-headed throngs of Patriots.
Cousin Stephen Greenleaf
Stephen Greenleaf was born in 1704 to Daniel (3C8X) and Elizabeth Gookin Greenleaf. His parents owned an apothacary shop in Boston and Stephen's mother became known as the first female apothacary in America. We wrote about his parents in our last post, "The Greenleafs." Stephen graduated from Harvard in 1723 and received an honorary degree from Yale 1750. He started his working career as a clerk in a Boston store, then tried his hand as an insurance underwriter. Those jobs were small potatoes. Cousin Stephen's main claim to fame turned out to be his stint as sheriff of Boston from 1757 to 1775.
Below is a portrait of Cousin Stephen painted by John Wollaston the Younger ca. 1750, a few years before he became sheriff. Stephen would have been about forty-six years old at the time.

Stephen and his wife had seven children but two of them died very young. When he was appointed sheriff in 1757, he had five daughters, the youngest thirteen. With a growing family, Stephen probably appreciated those first few, relatively peaceful years on the job. He did, however, have an early run-in with Samuel Adams who, along with John Hancock, would become the face of the impending Revolution.
Samuel Adams had wracked up debt from early investments in the then defunct Land Bank. It was poor Cousin Stephen's job to foreclose on Adams' property and sell it at auction but he soon found that he had come up against a formidable opponent. From the book Patriots by A.J. Langguth:
At one point, he [Adams] had to take out advertisments warning Boston's new sheriff, Stephen Greenleaf, not to try and sell his house at public auction. A narrow escape on that occasion taught Adams a tactical lesson; he had made Sheriff Greenleaf back down by threatening to sue and by intimidating potential buyers.
Adams later described his technique: "...put your adversary in the wrong. And keep him there."
a final straw for the colonies
England and her colonies in America had survived a few minor tussels in their 135 year relationship but, for the most part, the partnership had been mutually beneficial. The final French and Indian War, which ended in 1763, proved to be the straw that broke the camel's back.
In 1765, only two years after the war's end, both England and her American colonies were reeling with debt. The income Britain extracted from the colonies through duties on imports and exports no longer seemed sufficient. For the British Parliament, the answer to England's economic woes appeared to be simple. Since all those wars with the French had helped the American colonists as much as it had British subjects in England, it was time for the colonies to do their part in covering the cost.
While it's true that the split between England and her colonies might have been inevitable, had Britain known the powder keg she was igniting, she may have chosen another path.
the Stamp Act
In order to solve England's finacial woes, Parliament came up with what they thought was a brilliant idea. Tax every blooming piece of paper that the colonists put their hands on. The Stamp Act, passed in 1765, required a tax stamp for the use of all legal documents and printed materials. The law applied to wills, deeds, newspapers, and pamphlets with playing cards and dice thrown in for good measure.
The colonists had always put up with the endless import/export duties they had to pay, but the Stamp Act was the first direct tax levied on them. To add insult to injury, part of the revenue would be used to house regiments of British soldiers in America to "maintain peace between Natives Americans and the colonists." Worse still, violators of the Stamp Act could be tried and convicted by juries of their peers. Needless to say, the colonists did not take kindly to the Act.
With a rallying cries of "No taxation without representation," mobs gathered to try and intimidate stamp collectors into resigning. In our last post, we wrote about the Sons of Liberty who marched through Boston with an effigy of the stamp distributor, Andrew Oliver. Oliver's effigy was hung from the Liberty Tree and beheaded. Then his home was ransacked. Oliver finally resigned.
Other colonial towns followed suit as mobs in seaport towns turned away ships carrying the dreaded stamp papers. The scare tactics finally worked. By early 1766, most of the stamp distributors had resigned and the British government found it impossible to enforce the Act.
In March, the Stamp Act was repealed.
Score one for the colonists. But the Stamp Act had lit a fuse that would begin exploding in five short years and wold create some havoc for Cousin Stephen.

troubled times begin
The Stamp Act ignited the first of many troubled years to come in the struggle between Britain and her colonies in America. Things were so turbulent, according to Annie Haven Thwing in her Crooked and Narrow Streets of Boston, that "Sheriff Stephen Greenleaf had erected a new set of gallows on the Neck. . .on a little rising spot of ground. . ."
Major trouble started on August 14, 1765, when Andrew Oliver, who was the distributor of the stamps for Massachusetts, was hung in effigy from an elm tree.
Note: That same tree later became known as the Liberty Tree, increasingly used by the Patriots as a meeting place and also as a symbol of their struggle.
Thomas Hutchinson, the British Lt. Governor of Massachusetts, told Sheriff Greenleaf “that it was his duty to take some of his officers & go & cut it (the effigy) down & bring it away.” But the crowd surrounding the tree was large, fierce and very angry. The the sheriff's entreaties only made them angrier. Governor Francis Bernard later wrote about the incident: "...the Sheriff reported, that his Officers had endeavoured to take down the Effigy; but could not do it without imminent danger of their Lives."

When the angry mob then decided to go to Oliver's house to confront him, Lt. Governor Hutchinson decided to take action himself, dragging poor Cousin Stephen along with him. From a manuscript held by the Massachusetts Historical Society we learn that:
Some of the Mob went to the Secretarys [i.e., Oliver’s] House. The Lieut Governor who it is said followed them there with the High Sheriff drew their Swords and threatened them further that they got one or Two of them into a Room and shut the Doors in order to secure them, upon which the Mob was enragd and upon an Alarm given Crowds poured down from Fort Hill entered the House and the two great officers of State fled.
Evidently a "volley of stones" had been thrown at the two men before they hightailed it out of there. Luckily, Oliver had gotten himself and his family out of the house before the mob arrived.
An excellent description of the events of that day is found in a letter written on August 15 by our cousin Cyrus Baldwin (3C7X) to his brother Loammi (3C7X). Cyrus began his letter by telling Loammi that he would not be able to visit him in Woburn because he had devoped a boil on his face. Then Cyrus got right into the juicy details of the day before. I've corrected some of his grammar to make it easier to read.
Yesterday we had something so rare as to draw the attention of almost the whole town. It was no less than the effigie of the honorable Stamp Master of this province hanging on one of the great trees at the south end. . .behind him was a boot hung up with the Devil Crawling out, with a pitchfork in his hand. on the Effigies right arm was writ and sew’d on the letter A (for Andrew Oliver). On his left arm was wrote these words (It’s a glorious sight to See a Stamp man hanging on a Tree) on his breast was a large paper framed and the line much like what follows: Fair freedoms Cause I’ve meanly Quited, For the sake of a little (unreadable), The Devil has been outwitted, And now I have hung myself. He that takes this down is an enemy to his country.
This effigie hung in this manner all day, though the Sheriff with another officer or two went and ask’d liberty to take it down but to no purpose, after sun set. . .the mob Increased every moment and they took the Image down. . .it was brought by the mob through the main street to the townhouse. . .proceeded to the suppose’d stamp (office) near Oliver Dock and in less than half an hour laid it even with the ground then took the timbers of the house and cary’d ‘em up on Fort Hill where they stamp'd the Image & timber & made a great bonfire. At length, the fuel fail’d they immediately fell upon the stamp Masters garden fence took it up stamp’d and burned it. . .Not contented with this they proceeded to his Coach house took off the doors stamp’d ‘em and burn’d ‘em. while they was doing this the Sheriff began to read the the proclamation for the mob to withdraw (the Riot Act). Which Insens’d the mob so much that they fell upon the Stamp Masters dealing house broke glass casements and all, also broke down the doors, entered the house and despoil’d good part of the house & furniture, braking the looking glasses which some said was a pitty, the answer was that if they would not bare (bear) stamping they was good for nothing. The Coach & booby-hutt (sled) were drag’d up the Hill and would have been stamp’d & burnt had not some gentlemen opposed it & with much difficulty, that prevented it. They contnu’d their fire till about 11 o'Clock then retired. I believe people never was more Univassally (Universally) pleas’d, not so much as one could I hear say he was sorry, but a smile sat on almost every ones countenance. It is reported that Mr. Oliver, the said Stamp Master wrote to the Governor and Counsel that it was not worth while for him or any body else to accept the office of stamp master in this place. . .Tis hop’d what mr. Oliver has suffer’d will be a sufficient warning to others not to take offices that Encroach upon American liberty. Thus I have endeavored to let you a little into the Transactions of the two last days. It is now time to Conclude this long Epistle which I do by Subscribing my self your ever Loveing Brother. C. Baldwin
P.S. My face is much better. I had a comfortable night, but shall not come up till next week.
Stamp Master Oliver did, indeed, resign his positon. But Cousin Stephen's travails were not over by a long shot. When Lt. Governor Hutchinson's house was also ransacked by an unruly mob, the sheriff was sent out to arrest the ringleader, Ebinezer Mackintosh. In his book Patriots, A.J. Languth describes what happened:
When he spotted Mackintosh...the sheriff summoned up his nerve and took him to jail. Very soon, a group of gentlemen sought out Greenleaf and delivered a potent threat. Although the Town Meeting had voted to send out patrols to prevent any further rioting, no man would agree to go that night unless Ebenezer Mackintosh was set free. Greeleaf returned to the Counsil to report that unlimatum.
Hutchinson listened to the sheriff's story. "And did you discharge him (let him go)?"
"Yes," said Greenleaf.
"Then you have not done your duty."
Poor Cousin Stephen, getting it from all sides, just couldn't win. To everyone's relief, the stamp Act was repealed seven months later in March 1766.
the Beacon Pole escapade
Still, the fuse had been lit. And it appears that Britain had learned nothing from the furor caused by the Stamp Act. A year later, they tried another tact. In 1767, they passed the Townshend Acts which levied taxes on goods instead of paper. The Americans were having none of it. The hue and cry was so severe that, in 1768, Britain decided that sending troops from Halifax, Canada over to Boston would be a good way to restore some semblance of order.
The Patriots response to the news that the British were coming was to put in place an alarm system. The highest point in Boston was known Beacon Hill. A pole had been placed at the highest spot to be used as a beacon in case of emergency. For the Patriots, the arrival of the British surely constituted an emergency situation and they planned to use the Beacon Pole to their advantage. In his History of Massachusetts, Lt. Gov. Thomas Hutchinson wrote about the incident which again required the services of of good Sheriff Greenleaf.
An empty barrel was procured, and, being filled with turpentine, was privately, by night, hoisted up into this skillet. This. . .was to be fired when the fleet from Halifax should appear in sight. There could not be a plainer insult upon the governor's military authority. . .The council, thereupon advised the governor to direct the sheriff to cause the barrel to be forthwith removed. The sheriff, in the most private manner he could, executed his order taking six or seven men with him just at dinner time, and in about ten minutes, luckily as he thought, effected his purpose.
Note: Thomas Hutchinson, Lt. Governor of Massachusetts at the time of the Beacon Pole incident would go on to become governor. The third volume of his History of the Province of Massachusetts covered the years 1750 through June 1774. It was published posthumously in 1780.
Below is a 1768 drawing of Boston Commons with John Hancock's magnificent house in the upper right corner. Just right of Hancock's house is Beacon Hill with the pole atop.

the Liberty riots
The ever recalcitrant Americans attempted to counter the Townsend Acts in two main ways. First Boston merchants were encouraged to boycott all British imports. Second, many importers began smuggling their taxable goods into port. One such smuggler was Daniel Malcolm who would play a part in the Liberty riots. In September of 1766, Daniel was suspected of smuggling in sixty casks of wine to avoid the tax. Action needed to be taken. On September 24, Sheriff Greenleaf was dispatched to search Malcolm's house. Paul Revere, a witness to the happenings, gave testimony:
. . .they told me they understood the Custom House Officers were agoing to break open Capt. Malcom’s house to search for some casks of Wine that had been run...a number of Gentlemen gathered round him, soon after Mr. Tudor came and then Mr. Sheriff Greanleaf, I saw a number of People gather round him but I did not hear any of their discourse only Mr. Greanleaf asked them if they would assist him in the discharge of his Office...I think I heard Mr. Benjn. Goodin say he would assist him out of doors but would not go into Capt. Malcom’s house.
Sheriff Greenleaf and the Customs officers left the scene to acquire a search warrant. When they returned, Daniel Malcolm had managed to round up a few hundred men and boys to block anyone trying to enter his house. The intimidated officials backed down. Daniel Malcom's house was never searched and the charges against him were dropped.
Note: Ironically, Daniel Malcolm's own brother, John, was a Custom's officer who was tarred and feathered in 1774.
The Malcolm incident, however, only served to heighten goverment suspicions about smuggling. John Hancock was a known smuggler who had amassed quite a fortune doing just that. On June 10, 1768, two years after Cousin Stephen's attempt to search his house, Malcolm just happened to be in his store on John Hancock's wharf when Custom's officials arrived with orders to seize Hancock's sloop, Liberty. Outraged, Malcolm sounded a hue and cry to the general public. What ensued was another one of the Patriot's infamous riots.
About 3,000 men and boys congregated at the wharf. The Custom house was attacked and the chief collector of customs and his son were assaulted. Customs officials and British sailors on shore fled to the British warship Romney and finally to the fortress Castle Williams on Castle Island in Massachusetts Bay.

On June 13th the following notice was posted on the Liberty Tree:
The Sons of Liberty. Request all those, who in this time of oppression & distraction, wish well to, & would promote the peace, good order & security of the Town & Province, to assemble at Liberty Hall, under Liberty Tree, on Tuesday the 14th. instant, at Ten O’Clock forenoon precisely.
Upon seeing the notice, Sheriff Greenleaf dutifully informed Governor Bernard who later wrote of the affair, with evidently some embellishment:
Before I went to Council, the Sheriff came to inform me that there was a most violent and virulent paper stuck up upon Liberty Tree, containing an Invitation to the Sons of Liberty to rise that Night to clear the Country of the Commissioners & their Officers, to avenge themselves of the Officers of the Custom-house, one of which was by name devoted to death: There were also some indecent Threats against the Governor, if he did not procure the release of the Sloop which was seized.
All charges against Hancock were eventually dropped, but his sloop was never returned to him. The Liberty, while in British hands, spent some months patrolling the Rhode Island coast for smugglers. It was finally torched in July of 1769 by angry colonists after its crew seized two American ships.
The Liberty Riots taught the British Parliament nothing. Their answer was to pass even more restrictive laws on the colonists. Governor Bernard demanded that the Massachusetts House of Representative nullify a circular calling for unity against the Townshend Acts. All ninety-two representatives of that House refused to comply. The names of the ninety-two delegates were commemmorated on a silver bowl crafted by Paul Revere. The Liberty Bowl is now housed in the Museum of Fine arts in Boston

Next up: Poor Cousin Stephen Greenleaf's woes continue as British troops from England arrive to restore order in Boston.
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