How Boston’s Street Gangs Sparked the American Revolution

The sentencing hearing for notorious Boston crime boss Whitey Bulger begins today. Bulger is a prominent figure in Boston journalist George Hassett’s Gangsters of Boston, which was published earlier this year. The book is well worth a read to learn about the long history of the city’s crime scene. Published below is an excerpt which emphasizes that Bulger’s chapter in Boston crime lore is just that — a chapter. Boston gang activity, Hassett shows, not only predates the American Revolution; in many ways, it set it off.


THE PATRIOTS HAD waited long enough. After months of planning, they would strike as the sun came up.

To prepare, they worked frantically — buzzing around a grand old elm tree on a darkened Boston street corner. As the crowd swelled to thousands, one man was looked upon as the undisputed leader.

It wasn’t a future founding father; instead, a red-faced gang chief was calling the shots. At various times imprisoned and deemed a drunkard, today Ebenezer Mackintosh finally had the chance to prove his dedication to liberty.

To attack the British crown, he summoned the laborers, fishermen and seamen from the rough and tumble ranks of the town’s waterfront community. Also, members of the town’s perpetually warring street gangs were there. Each of them, however, respected Mackintosh and followed his command as the night wore on. Mackintosh even accepted the extravagant title “First Captain General of the Liberty Tree” in recognition of the tree they toiled under.

As dawn broke, the shocking scene was finally revealed: hanging from the tree was an effigy of a man. The effigy was labeled “AO” for Andrew Oliver, the British official appointed to oversee the hated new tax plan in the colonies. Attached was a verse: “A godlier sight who e’er did see/ A Stamp-Man hanging on a tree!”

The tax, referred to as the Stamp Act, was considered an economic attack on Boston’s port. Now, Boston’s rowdy waterfront laborers were fighting back. Mackintosh directed the crowd to Kilby Street to demolish Andrew Oliver’s nearly completed office building. They ransacked and plundered the building, savaging only wooden planks to build a massive bonfire.

Next, they attacked the home of a customs official and “liberated” cases of wine from his basement. By dinnertime the mob was at Governor Thomas Hutchinson’s mansion, beating on the doors with bars and axes, demanding to be heard.

Mackintosh, already very drunk, raised his voice again as the undisputed leader: the family must leave. Though Governor Hutchinson initially stood his ground, his daughter finally persuaded him to flee with the rest of the family. The “Mob was so general and so supported that all Power ceased in an instant,” Hutchinson later wrote back to England.

Acting with a disciplined frenzy, rioters labored until three o’clock in the morning to reduce one of New England’s grandest houses to a naked shell, missing its walls, floors, and certainly its most valuable contents.

In A People’s History of the United States: 1492 to Present, historian Howard Zinn identified the Stamp Act riots as the moment Boston’s elite began to wonder if class hatred could be focused against the British. The people now, at this intoxicating moment, seemed really to be considering the prospect of anarchy.

In the following days, loyalists to Britain set their first priority: move against the chief of the mobs, Mackintosh. Sheriff Greenleaf was ordered to arrest Mackintosh, who he soon spotted on the corner of Green Street. Mackintosh gave himself up without a struggle, confident his stay behind bars would be brief. He was right: at day’s end, a number of men arrived at the jail and instructed Greenleaf to hand over his keys so they could free the prisoner.

The sheriff, caught in between powers beyond his comprehension, could only agree with those who seemed to be in charge at the moment. Power had been shifted to the citizens and in their moment of authority they chose to rescue their hero Mackintosh.

In the streets, Mackintosh was seen as the boss, thanks to a reputation built not on words but bold action. When he was freed by Sheriff Greenleaf, it became clear that the American people themselves would produce and choose their own leaders. Before he was betrayed he would give the cause of liberty all he had.

The history of Boston gangsters starts at the water’s edge where a busy port hardened the town’s character forever. In the seventeenth century, Boston had been the quaint refuge of Puritans but a generation after the Mayflower landed, the struggling town was forced to turn to the ocean for economic survival. Fishermen, seamen and waterfront laborers would break Boston out of the tight framework of Puritan governance and forever lend the city its rugged character.

From the moment commercial ships began sailing in and out of Boston’s port, smugglers made sure there were unrecorded items on board. On the other end of the social spectrum than the rowdy waterfront laborers, Boston’s smugglers included some of the most successful merchants and radical political figures in town.

William Molineux may have been the port’s most successful smuggler. His anger at the customs regulations he openly ignored later led to his role as the key organizer of the Boston Tea Party. Among the other sly merchants in those pre-Revolutionary years was the smuggler Thomas Hancock. Hancock rose from impoverished beginnings to build the greatest fortune in Boston. [His nephew John Hancock continued the smuggling tradition and was referred to as “The Idol of the Mob.”]

Vice flourished too; prostitution was a constant presence in colonial Boston. In a 1650 journal entry, visiting Englishman Walter Muil Whitehill noted, “there’s perhaps no town of its size cou’d turn out more whores than this could.” By the mid-1700s, the western side of Beacon Hill was designated on several maps as “Mount Whoredom” for its plethora of prostitutes. Men of this generation might have visited the house of one of the town’s bawdiest women, Alice Thomas, a tavern owner know as the “Massachusetts Bay Madam.”

The elite class was just as likely to indulge in vice. John Hancock continued a long relationship with a woman, said to be “a common prostitute,” whom he kept as his mistress prior to marrying Dorothy Quincy.

Piracy also flourished in Boston’s maritime culture in the early and mid-eighteenth century. Widely accepted among the waterfront mobs, no seaman or fisherman dismissed the possibility of the pirate’s life. A short tour of duty under the skill and crossbones might help get his family through a period of unemployment.

A big heist could buy a spot among the town’s most prestigious social and political circles, as was the case with the Quincy family. Their ship, the Bethel, carried twenty-four guns and 110 men; a “letter of marquee” authorized her captain to seize perceived enemies as prizes and and to divide the spoils among officers and men. In 1748, Bethel came upon a Spanish treasure ship bound for home in Cadiz. After a bloody contest, the Americans triumphed, bringing back to Boston a reputed hundred thousand pounds of gold. It was enough to buy the Quincy family admission to Boston’s most elite class. Boston’s underworld was beginning its unlikely alliance with the city’s wealthy elite.

Boston’s Mobbish Spirit is Born

With the influx of irreverent seafaring types, Boston was losing its reputation as a quaint, pious town. Instead of Puritans, waterfront laborers were shaping the events of the day. In 1690, a violent mob chased Governor Edmund Andros after he cracked down on smugglers. Between that time and 1765, Boston’s maritime crowds provoked and participated in 28 riots and illegal actions compared to just four and six in the comparable ports of New York and Philadelphia. The city was singled out in the press for its “mobbish spirit.”

However, the port continued to stand as the colonies’ busiest: more than 500 vessels sailed out of its harbor to distant lands each year. As business boomed, a unique streetwise mentality continued to develop at all levels of the community, particularly in regards to tipsters and informants.

The lowest category of vermin on the waterfront was the tipsters, local seamen who for various reasons (usually money) informed on their smuggling skippers. In 1701, a tip from a sailor alerted customs officials to an illegal cargo on the ship Bean and Cole/ The owners were convicted and fined but after the trial, the presiding judge caught up with the tipster in the street and berated him for being a snitch.

Far more humiliating for accused informants was the practice of tarring and feathering. To put a “Yankee jacket” on a snitch was a cruel and inhumane practice but it serves its brutal purpose. Historian Ben Irvin describes how it worked:

Having captured an official or informant, the crowd would first apply the tar… Some victims were fortunate enough to be tarred over their clothes or protected by a frock or sheet. Others were stripped, and the tar was brushed, poured, or “bedawbed” over their skin…After the tar came the feathers.

Then came the traditional process of throwing the victim up on a “one-horse cart” and parading him through the streets while crowds of people cheered, sang, and made rough music with pots and pans.

In October 1769, a tipster for the British named George Gailer informed the authorities of John Hancock’s smuggling activities. Gailer received a brutal tarring and feathering from a relentless crowd of hundreds. He later tried to get back at his attackers by filing suit against two merchants and five seamen. His suit was denied: the punishment had been sanctioned and approved by the public.

The cutthroat culture of the waterfront was not just changing Boston: in the 1760s mob actions led by Boston gang leaders would plant the seeds for riots and a revolution.

The Ballad of Ebenezer Mackintosh: Gang Leader to Founding Father

At the top of Boston’s wild mobs stood — well, sometimes stood, sometimes slumped and sometimes fell drunkenly — Ebenezer Mackintosh.

Tracing his heritage to a ship of Scottish prisoners captured in battle then shipped to the New World and bonded servants, Mackintosh was born to a family living at the lowest levels of colonial society. His father, Moses, was kicked out of Boston in 1753 as a nonself-supporting individual, having failed to find a living for himself and his son (his wife died two years earlier). When Moses left town as an outcast, his ambitious son stayed behind.

Ebenezer, described as “slight of build, of sandy complexion and a nervous temperament,” first came to the town’s attention in March 1760 during a terrifying fire. Raging through the wooden structures of the waterfront, the blaze destroyed hundreds of homes, warehouses and taverns.

Mackintosh, in particular, earned praise from the authorities for his energetic work. Even Sheriff Stephen Greenleaf, who would later throw him into jail, recognized Mackintosh’s bravery and tapped him to lead a volunteer fire department.

Mackintosh was a natural leader with a knack for survival, qualities he hones in a punishing tour of duty in the French and Indian War. But he would be tested by Boston’s underworld of gangs and mobs where deep divisions separated warring neighborhoods.

There had always been a split between the North End and the South End inhabitants — the latter resenting the more established neighborhood for its superior attitude. To strengthen out the divisions, neighborhood gangs clashed in mob violence and large-scale gang fighting. Mill Creek, the border line between the two districts, became the usual spot for moonlight battles of Boston’s angry and disconnected seamen and landsmen.

The two gangs, known as South End Forever and North End Forever, met formally for battles each November 5 as part of so-called Pope’s Day. The celebration honored the plot against Parliament staged by Guy Fawkes and others, which was foiled on that date in 1605.

Typically, the violent celebrations began with two competitive parades marching at each other from the rival ends of Boston, and reached a climax with a massive bonfire and brawl at the town’s center. There, the North End and the South End gangs each sought to topple and make away with the effigy of the Pope that the other had prepared.

Pope’s Day in 1764 loomed as particularly menacing with the town more divided than ever. For Ebenezer Mackintosh, however, the day promised to be grand: an opportunity to lead his South End gang to long-sought victory and for him to demonstrate his hard-won leadership.

The celebration spun out of control early in the North End when that gang’s cart ran over the head of the five-year old boy, killing the lad instantly. Sheriffs, ordered to close things down, began destroying the effigies of the Pope from both the North End and the South End.

Although the officials succeeded in grabbing the North End effigy and pulling it to pieces, the South Enders, led by Mackintosh, fought back ferociously and kept their effigy intact. Winning that ability and demonstrating that authority no longer belonged to the sheriffs but to the people, Mackintosh led his crew northward and encountered their rival at Mill Bridge. There the battle became bloody; one account reported “many were hurt and bruised.”

Mackintosh led his gang to victory by but the glory was short lived as he was later arrested. With the powerful weight of the gangs pressing on the authorities, he was quickly released. His men seized what was left of North End Forever’s dummy and burned it in a bonfire. The crowd of several thousand cheered and hailed Mackintosh and his men. Mackintosh, in the town of his birth and his father’s disgrace, was savoring the salutes and feeling a special triumph as he looked over the adoring crowds.

Nine months later, when Mackintosh led the Stamp Act riots, his rise from gang leader to radical political figure was near complete. After the riots, he was appointed a “sealer of leather” — inspecting and approving the quality of material on behalf of the town — a move that signaled approval from the town’s political elite. Although he had come a long way, Mackintosh still had his most shocking move against the British in store.

The Triumph of Ebenezer Mackintosh and the Birth of the United States of America

With the anarchy and destruction of the summer’s Stamp Act riots still fresh in the minds of authorities and the gangs, the town prepared for a bloody Pope’s Day in fall 1765. The hated Stamp Act was scheduled to go into effect just four days before the annual violent celebration and the fear reached all levels of the town.

Then on the morning of November 5, effigies appeared hanging once again on the Liberty Tree. A crowd rapidly assembled and, not long after noon, the people could hear the sounds of trumpets and drums. But then, to their surprise, down the streets leading to town center came into view two beautifully disciplined teams, led by Mackintosh and his old rival, the North End’s Henry Smith. Loyalist Peter Oliver was among those to express his amazement that these two men were not leading armed men against one another. He described how Mackintosh “Paraded the town with a mob of armed Men in Two Files, and passed by the State House when the General Assembly were sitting to display his power…when he had fully displayed his Authority, he marched his Men to the first Rendezvous & ordered them to retire peacefully to their several Homes and was punctually obeyed.”

“What happened here?” Oliver and other British officials must have asked themselves. How did these two gangs who had gone at each other’s throats (with sticks and knives) each year for as long as anyone could remember, come together peacefully without conflict?

Unknown to them, the answer lay in the “Union Feast” that many of the gang members had shared the night before. Arranged by Samuel Adams and John Hancock, the feast had succeeded in uniting the divided town. This rolling event, a series of dinners at Boston’s most popular taverns, allowed all classes of men to come together with, “Heart and and in flowing Bowls and bumping Glasses.”

So when the two files of marchers came together on this Pope’s Day, Ebenezer Mackintosh and Henry Swift bowed to each other with great formality under the Liberty Tree, and the violent mobs easily avoided any conflict.

But was Mackintosh selling out? The staged event could be viewed as mob bosses Mackintosh and Swift, betraying the real intentions of mobs and giving them over as dupes to the more powerful Hancock and Adams.

However, Mackintosh was no fool. He had brought the people into the American political picture and never again could they be totally excluded. In the political debates to come in the American Revolution, his symbolic voice — and the roar of the mob behind him — had to be heard. As Andrew Oliver ruefully put it, “The People, even to the lowest Ranks, have become more attentive to their liberties.”

In fact, the last dramatic scene in the Stamp Act belonged to Mackintosh, with Andrew Oliver playing a degrading role. Oliver, the man who seemed to epitomize the hated tax, promised to resign after the Stamp Act riots in August but by winter he had yet to step aside.

On December 17, during a bone chilling rainstorm, Oliver was forcibly led to the Liberty Tree by none other than Ebenezer Mackintosh. Before a throng of more than 2,000 soaked but jubilant spectators, Oliver swore to take no steps “for enforcing the Stamp Act in America.”

This performance at the end of 1765 was a thoroughly humiliating personal experience for not only Oliver but also his entire species. To bend to the will of the crowd, a crowd led by a lowly, red faced shoemaker such as Mackintosh, was an unprecedented development in an age of deference to the higher born.

In the summer of 1774, Mackintosh crossed the Neck and left Boston behind, a widower trudging inland with his two young children. As they walked to New Hampshire, they marched in company with others — Boston was no longer a safe place for poor, unemployed families — particularly when the father was a known rioter, possibly with a price on his head.

In one sense Mackintosh was a retreating hero: a lower class leader of rebellion who served a useful purpose only during certain crisis, after which he was regarded by upper class Bostonians as an untrustworthy, riotous blabbermouth. His influence, however, would be felt in Boston as Patriots declared their liberty. The rage of Boston’s toughest crowds — the angry gang members, seamen and fishermen — had been transformed into a push for change in the order of human affairs, a them for the American Revolution that would soon follow.

Pope’s Day image from Wikimedia Commons

  • hilary lee

    I am a descendent of Ebenezer Mackintosh. Interesting to learn his story and his involvement in the American Revolution.