When you think about the top ten most ruthless figures ever to grace the silver screen, gangster movies instantly spring to mind. These outlaw icons have captured audiences worldwide, letting us vicariously relish the thrill of law‑breaking, bloodshed, and swagger. While the world at large clocks in at nine‑to‑five jobs, these cinematic bad‑boys choose a life of robbery, murder, and mayhem—often with a style that makes us both gasp and grin.

Top Ten Most Ruthless: What Makes These Characters Stand Out

10 Vincenzo Coccotti: True Romance

Vincenzo Coccotti serves as consigliere to Detroit’s own “Blue” Lou Boyle, and up until a fateful night he’d managed to keep his hands clean since 1984. That changes dramatically when Clarence Worley and his new bride, Alabama, pilfer Boyle’s stash of cocaine from Alabama’s former pimp, Drexl. Christopher Walken embodies Coccotti with a chilling, palpable menace, looming over a bound‑up Dennis Hopper—who plays Clarence’s father—as he interrogates him with ruthless ferocity for his son’s whereabouts.

Clarence’s dad, refusing to be cowed, hurls a barrage of insults at Coccotti’s Sicilian roots, finally provoking the mobster to snap and shatter his decade‑plus no‑kill streak. The scene has become one of Quentin Tarantino’s most unforgettable moments, and Walken delivers a masterclass in unhinged fury when his pride is bruised.

9 Tony Montana: Scarface

One of cinema’s most quoted lines belongs to Scarface, chronicling the meteoric rise (and violent fall) of Tony Montana. Early on, a terrifying encounter with chainsaw‑wielding thugs leaves an indelible mark. Instead of turning away, Montana decides to mirror their brutality, propelling himself deeper into Miami’s drug underworld.

His descent accelerates as he betrays those closest to him and even abuses the cardinal rule of drug lords—getting high on his own product. By the climax, Montana unleashes an arsenal he dubs his “Little Friend,” mowing down an army of assassins in a blood‑soaked, iconic showdown that still reverberates through gangster cinema.

8 Mr. Blonde: Reservoir Dogs

Quentin Tarantino’s debut, Reservoir Dogs, has earned cult status, and Mr. Blonde stands out as a terrifying embodiment of senseless violence. Though the heist itself is never shown, the film’s non‑linear storytelling reveals Mr. Blonde’s penchant for arbitrary cruelty. After the robbery goes sideways, he pauses for a burger and a soda, then kidnaps a police officer on his way to the rendezvous.

In a chilling display of disregard for life, he slices the cop’s ear off while a 1970s soft‑rock track plays, dancing through the carnage with a twisted glee. Not the mastermind, he epitomizes the gangster who can’t be trusted—neither friend nor foe is safe from his unpredictable brutality.

7 Carlito Brigante: Carlito’s Way

Carlito Brigante isn’t your run‑of‑the‑mill mobster; at the film’s start he’s freshly released from prison, yearning for a straight‑and‑narrow life. Yet his past is a tapestry of ruthless deeds, and his reputation haunts the streets long after his incarceration. Al Pacino delivers a nuanced performance, whispering, “The streets are watching,” a nod to his infamous legacy.

Determined to retire in the Bahamas with his love, Gail, Carlito’s attempts at legitimacy are thwarted when his young cousin unwittingly drags him into a botched drug deal. The tension spikes as Carlito is forced to open fire, eliminating the dealers to secure his escape.

Although he craves peace, his seasoned instincts and cold‑blooded efficiency cement his status as one of cinema’s most formidable and ruthless gangsters.

6 Keyser Söze: The Usual Suspects

According to the slick‑talking con‑artist Roger “Verbal” Kint (Kevin Spacey), Keyser Söze is a phantom crime lord whose legend looms larger than life. The film’s twists blur truth and myth, ultimately revealing that Kint and Söze may be one and the same. Inspired by real‑life murderer John List and the espionage thriller No Way Out, Söze’s backstory is shrouded in ambiguity.

Söze distinguishes himself as the sole figure on this list who blends cold‑blooded murder with Machiavellian cunning. Whether a Hungarian drug czar who annihilated his own family or a fabricated myth, his primary weapons are terror and deception. His mastery of misdirection makes him an iconic, unforgettable gangster.

5 Tommy DeVito: Goodfellas

Based on the real‑life hitman Thomas DeSimone—dubbed “Two‑Gun Tommy”—Tommy DeVito is a feared associate of the Lucchese family. He evolves from fence to truck hijacker alongside Jimmy Conway, operating just beneath the crime boss Paulie Cicero. Tommy’s volatile temper and penchant for violence render him a valuable, albeit dangerous, asset.

By 1963, his sociopathic tendencies spiral out of control; even mundane conversations become perilous. He loathes being called “funny,” harasses civilians, and threatens coworkers. Ultimately, the mob decides to eliminate him, a grim scene that underscores his unchecked aggression and ruthless nature.

4 Michael Corleone: The Godfather Trilogy

Michael Corleone’s arc epitomizes the classic gangster saga. Initially the only son not slated for the family business, Michael graduates from an Ivy League school and serves in WWII. When a mob war leaves his father Vito wounded, Michael is thrust into the underworld.

His transformation begins with the cold‑blooded execution of rival Maffia Cappo and a police chief, spiraling into a cascade of calculated murders. By the trilogy’s end, Michael orders the hit on his own brother, Fredo—a chilling business decision that isolates him completely, leaving him bereft of love and loyalty.

3 Professor Moriarty: Sherlock Holmes

Sir Arthur Conan Doyle’s legendary arch‑nemesis, Professor Moriarty, has endured for over a century across books, comics, TV, and film. While Sherlock Holmes embodies brilliant detection, Moriarty represents the “Napoleon of Crime,” orchestrating vast networks of illicit activity.

Every major illegal venture in the city passes through his hands; Holmes famously describes him as the hub of half the world’s evil, the mastermind behind countless crimes. Moriarty’s intellectual supremacy and criminal reach make him a terrifyingly ruthless figure.

2 The Joker (Jack Napier): Batman (1989)

Since debuting in 1940’s Batman #1, the Joker has taken countless forms. In Tim Burton’s 1989 Batman, Jack Napier—a mob lieutenant—gets transformed after a vat of toxic chemicals, courtesy of Batman, into the iconic Clown Prince of Crime.

Napier’s pre‑transformation violence carries over; he embraces chaos, lacing products with lethal poison and even shooting his own henchman in the face. Jack Nicholson’s portrayal captures a mob boss gone mad, cementing the Joker as one of the most ruthless cinematic villains.

1 Bodhi: Point Break

Surprisingly, the laid‑back surfer Bodhi tops this list as the most ruthless gangster. Though he preaches a zen philosophy, his bank‑robbing crew mirrors classic outlaws like Bonnie and Clyde, stealing to fund an endless summer.

In reality, Bodhi shares more in common with Henry Hill’s ruthless pragmatism—if they want something, they simply take it. His hypocrisy shines: he preaches loyalty yet would betray anyone to protect himself, making his ruthlessness uniquely self‑serving.

There have been many links between organized crime and the entertainment industry over the years, especially during the Golden Age of Hollywood and the heyday of the nightclub circuit. While a lot of these associations were business related, some of the most exciting stories center on romantic relationships between gangsters and female movie stars, recording artists, and other celebrities. This is our top 10 female list of celebrated stars who were also known as gangster molls.

Top 10 Female Stars and Their Mob Ties

10 Donna Reed

Despite winning an Oscar for her steamy turn as Alma (aka Lorene) in the 1953 classic From Here to Eternity, Donna Reed cultivated one of the most wholesome images of any actress in the mid‑20th century, especially when she embodied the ideal housewife Donna Stone in her eponymous television series. It’s therefore all the more surprising that she was romantically linked to mobster Johnny Roselli (sometimes spelled Rosselli) in the late 1940s.

Roselli, a dapper and charismatic figure, blended seamlessly into Hollywood society, also courting stars like Lana Turner and Betty Hutton. Though celebrated for his diplomatic finesse and dubbed “The Henry Kissinger of the Mob,” Roselli was also implicated in several murders, according to author Douglas Thompson.

9 Gloria Vanderbilt

Heiress‑turned‑actress and fashion designer Gloria Vanderbilt led a drama‑filled life from childhood through a famous custody battle, four vivid marriages, and a myriad of careers. One of her most turbulent chapters involved the abuse she later recounted at the hands of her first husband, Pat DiCicco, whom she married at 17. DiCicco, a film producer and agent, was allegedly tied to the Lucky Luciano crime family. Thirteen years her senior, he had previously wed actresses Thelma Todd and Linda Douglas.

Vanderbilt, visiting her mother when the engagement was announced, rushed into marriage to avoid returning to her aunt, the prominent society matron and artist Gertrude Vanderbilt Whitney, who had previously won custody of her. She quickly wed DiCicco after a breakup with millionaire Howard Hughes, who had employed DiCicco as a press agent. Whitney was so opposed that she removed her niece from her will. Vanderbilt soon realized the union was a mistake; DiCicco proved violent and emotionally abusive. She eventually divorced him in 1945, paying a $350,000 settlement.

9 Phyllis McGuire

The McGuire Sisters were among the most beloved female singing groups of the 1950s, famed for their wholesome, minister‑daughter image—until lead vocalist Phyllis McGuire sparked scandal with a romance with notorious Chicago mafia boss Sam Giancana.

Giancana first noticed McGuire when she performed with her sisters at The Desert Inn in 1959, subsequently erasing a sizable casino debt she owed. Though she testified before a grand jury in 1965 that they were merely friends, McGuire later admitted a romantic involvement, claiming she didn’t know who Giancana truly was when they met. Pressure from the FBI investigation, which even placed listening devices in her bedroom, and damaging publicity forced her to end the affair. She later dated oil‑man Edward “Tiger Mike” Davis, while Giancana was killed by an unknown assailant in 1975. Their passionate liaison inspired the 1995 HBO film Sugartime.

8 Dona Drake

Best known for roles in classics like Kansas City Confidential and The Girl from Jones Beach, the sultry Dona Drake was a familiar presence in the 1940s and ’50s. Beyond acting, she sang, danced, and led a band. Yet one of her most intriguing chapters involved a romance with Brooklyn racketeer Louis “Pretty” Amberg, who, alongside his brothers, sought to dominate local racketeering.

Amberg’s ambition ultimately led to his downfall; his body was discovered in a burning car in 1935. Police interrogated the then‑early‑twenties Drake, who claimed she knew him only as “Mr. Cohn” and was unaware of his criminal activities. Despite the scandal, Drake’s career flourished, and she later enjoyed a 45‑year marriage to Oscar‑winning costume designer Travilla.

7 June Lang

Johnny Roselli didn’t limit his charm to actresses; he married rising star June Lang in 1939. Though not as famous as some of his other girlfriends, the pretty blonde enjoyed a successful run in films such as Footlight Serenade and Stage Door Canteen, produced around the time of their marriage. Nevertheless, Lang’s tie to the mobster—dubbed “Handsome Johnny”—ultimately harmed her career.

When Roselli was off‑screen handling Chicago mob business in Hollywood and Las Vegas, he also dabbled in film production, co‑producing several pictures. Lang insisted she was unaware of his criminal dealings during their union. Given Roselli’s ability to present himself as anyone he wished, it’s plausible she truly didn’t know his true vocation. The revelation of his mob ties prompted Lang to file for divorce in 1943.

6 Lana Turner

The tempestuous love life of film icon Lana Turner featured several gangsters, but her most infamous liaison was with Cohen crime family affiliate Johnny Stompanato. Their relationship culminated dramatically when Turner’s 14‑year‑old daughter Cheryl Crane fatally stabbed Stompanato during a heated argument, fearing for her mother’s safety.

Stompanato’s possessiveness and violence were well documented; he not only assaulted Turner but also threatened co‑star Sean Connery, pointing a gun at him when he suspected an affair. On the night of his death, Turner was attempting to break up with Stompanato. Initially, she tried to protect her daughter by claiming responsibility herself, but the coroner’s inquest soon exonerated Cheryl, ruling the killing a justifiable homicide stemming from domestic violence. The case ignited one of Hollywood’s biggest scandals.

5 Jayne Mansfield

Considering the extensive time Colombo underboss Sonny Franzese spent in legendary nightclubs like the Copacabana, it’s unsurprising he crossed paths with high‑profile celebrities. Among those was iconic actress Jayne Mansfield, who, according to Crime Reads, was “madly in love with” Franzese.

The two met at The Latin Quarter nightclub, where Mansfield, a voluptuous blonde, appeared unexpectedly onstage and caught Franzese’s eye. At the time, she was married to bodybuilder‑actor Mickey Hargitay. When Mansfield warned Franzese that her husband would escort her home, Franzese allegedly threatened to beat Hargitay if he showed up. Their romance, however, remained casual as Franzese continued to “play the field.”

4 Jean Harlow

It’s easy to picture the brash, saucy Jean Harlow as a gangster’s moll, and she indeed dated infamous mobster Abner “Longie” Zwillman. In 1930, Zwillman bolstered Harlow’s fledgling career by loaning Columbia Pictures mogul Harry Cohn $500,000 in exchange for a two‑picture deal, propelling the 19‑year‑old from bit parts to stardom.

Harlow’s on‑screen roles often cast her as a gangster’s sweetheart, such as in Public Enemy (1931), cementing the flashy, brazen image of the 1930s moll. She married three times in her 26‑year life; after Zwillman—dubbed the “Al Capone of New Jersey”—her 1932 marriage to producer Paul Bern ended abruptly when Bern committed suicide just two months later.

3 Billie Holiday

Legendary jazz singer Billie Holiday endured a tumultuous personal life, plagued by addiction, an abusive childhood, and other hardships. Her love life added another layer of turbulence: her third and final husband, Louis McKay, whom she married in 1957, was a shady figure described as a wannabe gangster who abused her, stole her money, and allegedly worked as a mob enforcer.

The couple was once arrested together for narcotics possession. Holiday, fearing McKay, never reported his physical abuse. The final straw came when she learned he had lost her money in a risky venture. She left him, yet remained legally married until her death in 1959.

1 Marilyn Monroe

Given Marilyn Monroe’s wild, sometimes scandalous lifestyle, it isn’t surprising she tangled with high‑profile criminals. She’s been linked to several mobsters, including ladies’ man Sonny Franzese and reportedly Chicago boss Sam Giancana.

One of the most talked‑about rumors claims Giancana was with Monroe on her last full night alive, attempting to dissuade her from going public about an alleged affair with President John F. Kennedy. Monroe’s romance with Franzese formed a love triangle with ex‑husband baseball legend Joe DiMaggio, who remained infatuated with her. During Monroe’s famed “Happy Birthday, Mr. President” performance at a Madison Square Garden fundraiser, DiMaggio chased Franzese around the arena to confront him about the affair. Franzese later claimed he was ashamed for becoming involved with Monroe.

When we hear the phrase 10 notorious medieval gangsters, images of modern street crews rarely come to mind. Yet the Middle Ages were teeming with ruthless families, outlaws, and power‑hungry courtiers who ran their own shadowy empires. From crafty bandits stealing royal jewels to noblemen who turned rebellion into a lucrative side‑business, these ten characters proved that crime was as much a part of medieval life as chivalry and cathedral building.

10 Notorious Medieval Gangsters Unveiled

10 The Waraunt Family

Some criminal crews were nothing more than a tight‑knit family trying to stay afloat in a harsh world, and the Waraunts epitomized that model. Four siblings—Matilda, Margery, Richard, and a brother—joined forces with an additional male relative, forming a little clan that repeatedly slipped through the justice system while amassing a modest fortune by medieval standards.

The earliest record dates to 1321, when three of the siblings—Matilda, Margery, and Richard—were accused of receiving stolen goods. They escaped punishment, and the fourth sibling faced a similar charge later that year. While the exact value of the loot remains unknown, the family’s criminal streak continued unabated.

The turning point arrived when John Waraunt was convicted of stealing clothing and household items valued at eight shillings. To put that in perspective, a laborer in 1331 earned roughly three pennies a day; twelve pennies made a shilling, so eight shillings equaled about a month’s wages. John was hanged for the theft.

Undeterred, the remaining Waraunts kept pilfering. In 1325 they were imprisoned for allegedly stealing cloth worth 60 shillings, yet they avoided conviction despite the threat of forte et dure—a brutal form of torture. They were acquitted of a 32‑cloth theft in 1326, and later that year two sisters were cleared of a 40‑shilling accusation. By the end of their recorded saga, the family had pilfered the equivalent of over a year and a half’s wages and largely escaped lasting punishment.

9 Malcolm Musard

The first mention of Malcolm Musard appears on 13 February 1296, when he and several companions were caught trespassing in a royal forest while en route to join the king’s Scottish campaign. Likely in his early twenties, this incident marked the beginning of a life spent skirting the law.

Following his father’s death in 1300, Malcolm inherited lands in Worcestershire and quickly turned his sword into a profit‑making tool. By 1304 he and his gang were hired to assault a rectory, a line of work they would repeat for years. Accused of “many felonies, robberies and homicides” in the early 1300s, the group fled Worcestershire, only to be pursued again in 1316 when the king ordered an inquiry into Malcolm’s “diverse crimes” across Worcestershire and Warwickshire. He received a royal pardon in 1318.

Malcolm’s criminal career continued: arrested in 1323 for allegedly aiding the Marcher Lords’ rebellion, he was released in 1326 and formally pardoned for all outlawry in Worcester. Yet the pattern persisted—when Queen Isabella deposed Edward II in 1327, she ordered his arrest for theft, only for him to be freed again after Edward III’s 1330 pardon. His story illustrates a relentless cycle of crime, capture, and royal clemency.

8 Fulk FitzWarin

Not every outlaw chose the path of crime; some were forced into it. Fulk FitzWarin found himself at odds with King John after the crown granted the Whittington estate to a Welsh rival, despite Fulk having paid £100 for it and his father having fought for the property.

Refusing to accept the royal decision, Fulk rallied his brothers—William, Philip, and John—along with tenants and ambitious knights in 1200, forming a 52‑strong guerrilla band against the crown. Declared outlaws, they persisted for three years, even confronting Hubert de Burgh’s 100‑man force. By November 1203 the king relented, paying Fulk 200 marks and restoring Whittington. Thereafter, Fulk resumed a respectable noble life, living until 1258 and later acting as a trusted mediator in Welsh disputes, demonstrating how a brief outlaw stint could segue back into aristocratic respectability.

7 The Folvilles

In medieval England, primogeniture meant only the eldest son inherited the family estate, while younger brothers often sought fortunes as knights or mercenaries. Some, however, turned to a life of crime. The Folville clan embodied this divergence. The eldest brother, John Folville, kept a respectable noble façade, but his younger siblings—Eustace, Robert, Walter, and Richard—formed a violent mercenary band that operated beyond the law, especially when family interests were threatened.

In 1326, after Baron of the Exchequer Roger de Beler threatened the family, Eustace led a 50‑man force to capture and kill de Beler on a road. A warrant followed, prompting the Folvilles to flee to Queen Isabella’s continental army, which was preparing to depose King Edward II. Their participation earned them a royal pardon after the successful coup.

Back in England, the Folvilles became hired thugs, targeting the lands of those who had wronged them, such as Henry de Beaumont. Their notoriety grew when they seized judge Richard Willoughby, ransoming him for 1,300 marks—a staggering sum—after he attempted to convict them. Aligning with the infamous Coterel gang, they roamed Derbyshire openly armed, threatening travelers and committing systematic extortion.

When Edward III needed warriors for the Scottish wars, the Folvilles were recruited, fighting the Scots between 1337‑1338. In return, they received a full pardon, allowing them to evade any legal consequences for their prior misdeeds.

6 John Fitzwalter

John Fitzwalter, a powerful Essex magnate and close kin to the de Clare family, exemplified noble privilege run amok. He treated Essex as his personal fiefdom, wielding enough influence that even royal justices hesitated to prosecute him.

His criminal résumé began in 1340 when he joined a gang that broke into John de Seagrave’s park, hunting and vandalising the property. Soon, Fitzwalter’s own gang engaged in cattle‑rustling, extortion, and the outright theft of merchant goods, while consistently refusing to settle debts or rents owed to others.

Tensions peaked when men from Colchester raided one of Fitzwalter’s parks, looted it, and killed a member of his retinue—likely a retaliation. In response, Fitzwalter mobilised his forces, manipulated juries, assaulted non‑compliant jurors, and laid siege to the town, using salvaged wooden beams as weapons and blocking all entry and exit routes.

King Edward III finally intervened in 1351, commissioning a peace commission to investigate Fitzwalter’s crimes. An arrest warrant led to his imprisonment in the Tower of London for a year and the confiscation of his entire estate. Though eventually released and granted a royal pardon, he was ordered to pay a £847 fine—an amount many lower‑rank knights would never earn in a lifetime. He dutifully paid the fine in installments until his death a decade later, marking the end of his notorious career.

5 The Despensers

The Despenser duo—Hugh the Younger and his father—were more than ordinary thugs; they were master manipulators who, at the height of their power, effectively controlled King Edward II. By exploiting their courtly positions, they bullied nobles, seized lands, and amassed wealth, prompting a civil war that ultimately toppled them.

In 1317 Hugh Despenser the Younger became royal chamberlain, a role granting him direct access to the king. By 1320 he was Edward’s closest confidant, second only to the queen, Isabella. With this influence, he began extorting lands and titles from nobles at an alarming rate, consolidating his family’s grip on power.

Their overreach alarmed the aristocracy, leading to open rebellion in 1321. The rebels demanded limits on royal authority and the removal of the Despensers. Their plea was crushed at the Battle of Boroughbridge, allowing the Despensers four years of unchecked rule.

During this period, Hugh and his father systematically abused royal authority: imprisoning opponents until they surrendered charters, steering the king’s favour against rivals such as Roger Mortimer, and monopolising the monarch’s audience—preventing even the queen from meeting Edward without Despenser presence.

Their tyranny sparked nationwide outrage. When Queen Isabella finally landed with an invading force, demanding the Despensers’ removal, Edward’s reign collapsed. Within two months, Hugh and his father were captured. The elder Despenser was gruesomely dismembered and fed to dogs; Hugh met a horrific end—hanged from a 50‑foot pole, forced to wear his coat of arms upside down, then castrated and disemboweled.

4 Adam The Leper

While many medieval bandits roamed the countryside, some targeted bustling towns. Adam the Leper headed one such urban gang, recorded on page 245 of A History of Crime in England. His crew learned that a merchant, employed by Queen Philippa of Hainault, was safeguarding valuable jewels in his London home.

Seizing the opportunity, Adam led his men to the merchant’s residence after dark, barricading the owner inside and demanding the jewels. When the merchant refused, the gang set fire to the house, reduced it to ashes, and absconded with the treasure regardless.

Beyond this dramatic heist, little else is documented about Adam. He appears to have evaded punishment, living another two decades, likely heading a street‑level gang that specialized in similar robberies—most of which never entered the historical record because they didn’t involve high‑profile victims.

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Roger Godberd is frequently cited as a possible inspiration for the Robin Hood legend. Operating around Sherwood Forest, he was indeed an outlaw, but his deeds differ markedly from the merry‑men of folklore.

Legal records show that Godberd once assaulted a tenant, Jordan le Fleming, forcibly evicting him from a ten‑year tenancy after just a year and seizing some of his belongings. He was also accused of poaching venison in Sherwood in 1264. By 1266, he had taken a charter from the convent at Garendon at swordpoint, then compelled the monks to sign a document absolving him of the theft. That same year, the king granted him a royal pardon, citing “good behaviour.”

Despite the pardon, Godberd continued his criminal career. In 1270 he was charged with robbery and, by then, led a band of outlaws in Leicester, Nottingham, and Wiltshire. He was imprisoned in Nottingham Castle but escaped with aid from a knight named Richard Folyot. Later, he faced trial at Bridgnorth Castle in 1275, presenting his earlier royal pardon as defense. Sources diverge on his fate: some claim he died in prison the following year, while others suggest he lived for another two decades.

2 The Coterels

The Coterel brothers—James, Nicholas, and John—mirrored the Folvilles in both era and geography, collaborating in the kidnapping and ransom of royal judge Richard Willoughby. Their lineage traced back to Ralph Coterel, a Derbyshire landowner.

Their first appearance came during the 1322 rebellion of the Earl of Lancaster, where they fought alongside his forces against King Edward II. As royal authority waned, the Coterels expanded, protected by the priors of Lichfield, rendering them virtually untouchable. By 1330 they had raided the estate of Henry Lancaster, a powerful royal relative, and were listed as wanted for murder.

In a surprising twist, Queen Philippa extended protection to James Coterel, even assisting him in purchasing land in 1332 despite his ongoing criminal ventures. When war erupted between England and Scotland, a royal commission investigating their crimes was abruptly halted. In 1338 the Coterels were summoned to join the king’s army in Flanders, a request they gladly accepted.

Their military service paved the way for a full pardon in 1351. By then, James served as a tax collector for Lenton Priory, while Nicholas held the position of royal bailiff. The final record of James notes a debt of over £100 owed to the Folville gang, but his exact date of death remains unknown.

1 Johnnie Armstrong

John Armstrong, better known as Johnnie, was a border‑land raider and nobleman who commanded two forts in the contested region between England and Scotland. From roughly 1520 to 1530, his organized gang terrorised settlements on both sides, extorting villages, stealing livestock, and torching homes when victims refused to pay.

Although his criminal record was extensive, Armstrong officially served as a vassal to the Scottish Lord of the West March, Lord Maxwell, who shielded him from English attempts at prosecution. Frustrated, English Lord Dacre led an expedition that burned Armstrong’s property at Cannonby.

Political pressure eventually forced Scottish Lord Angus to declare Armstrong and his men outlaws. While Angus struggled to muster an army against them, the tide turned in 1530 when King James V of Scotland, determined to purge banditry, lured Armstrong into a meeting and ordered his execution. Armstrong and his 24 followers were hanged, despite his pleas and promises to make northern English men pay their yearly rents.