20. The New York Troubleshooter Called in to Solve a Chicago Problem
When the competition with the North Side Gang heated up, Al Capone called in his former boss, Frankie Yale. Born Francisco Iole in Calabria in southern Italy, Yale had arrived in the US at age eight. As a teenager, he joined the Five Points Gang, and quickly developed a violent reputation as a ferocious fist fighter and brawler, and was first arrested in 1912 at age nineteen for disorderly conduct. He grew up to become an early New York mafia leader and hitman, and had employed a young Al Capone in his operations.
Yale began his organized crime career as a protection and extortion racketeer, and in 1913 he was arrested for the robbery and assault of a dry goods store. He walked after the store owner retracted his identification of the culprit. By 1917, he had invested his rackets proceeds into a bar in Coney Island, which became his base of operations. His criminal enterprise typified a new trend in American Mafiosi “families”: the employment of Italians from all regions, and not just from the boss’ hometown or district as had been the case traditionally.
Unlike their hidebound predecessors, Frankie Yale and the new breed of Mafiosi to which he belonged were willing to cooperate and work with other ethnic gangs, so long as there was money to be made. From protection, he soon branched out into prostitution, and ran a string of brothels. When Prohibition arrived, Yale became one of Brooklyn’s biggest bootleggers. However, the high profits came with correspondingly high risks, and in 1921 he barely escaped an assassination attempt by rival bootleggers. He got away with a shot up lung, while one of his bodyguards was wounded and another was killed.
He survived another assassination attempt just a few months later, that claimed the life of another bodyguard. That was followed by yet another attempt in 1923, when he escaped with his life only because the assassins mistook an associate for Yale and shot him dead instead. In 1924, his former employee Al Capone asked him for a favor, so he travelled to Chicago with a hit team to murder North Side Gang leader Dean O’Banion, who was locked into a bitter feud with Capone and the Chicago Outfit.
18. The Murder of Dean O’Banion Did Not Settle the Feud With His Gang, But Merely Intensified It
Dean O’Banion owned a flower shop in Chicago’s North Side, so Frankie Yale and a team of Brooklyn hitmen visited, under the pretext of arranging floral arrangements for a mobster’s funeral. The visits were actually reconnaissance trips to study the layout of the place. On November 10, 1924, Yale returned to the store with two men. When he and the proprietor shook hands, his accomplices shot O’Banion in the chest and throat, then finished him off with a bullet to the back of the head. Rather than settle the feud with the North Side Gang, however, the murder merely intensified it, as O’Banion’s successor Hymie Weiss vowed revenge.
As to Yale, he was arrested, but was released when police failed to shake his alibi. Capone returned the favor a year later, when he helped Yale murder three rivals and wound a fourth in an ambush outside a New York City nightclub. The friendship ended in 1927 when Yale, Capone’s whiskey supplier, got greedy and began to hijack the Chicago gangster’s trucks. Negotiations failed to resolve matters, so Capone went after his former boss. On July 1, 1928, Yale received a call that something was wrong with his wife. Refusing to wait for his usual escort of bodyguards, he jumped into his armor-plated car and sped off, only to be intercepted en route by gunmen who riddled his vehicle and shot him to death with armor-piercing bullets.
In his first major act of revenge for the murder of Dean O’Banion, his successor Hymie Weiss went after the Chicago Outfit’s boss, Johnny Torrio. He was ambushed outside his apartment with a fusillade of gunfire, and took bullets to the jaw, lung, abdomen, groin, and legs. Severely wounded, Torrio was spared from a coup de grace shot to the skull when the killer’s gun jammed. The near death experience frightened Torrio, and convinced him to get out while he still could. So in 1925, he handed control of the Outfit to Capone, and moved to Italy.
Capone, who reportedly feared Weiss, tried to make peace and end the feud with the North Side Gang, but his offers were rejected. After repeated failed efforts by the rival bosses to kill each other, Weiss led a team of gunmen in 1926, that fired over 1000 bullets into Capone’s headquarters. Capone survived, and returned the favor a few weeks later. On October 11, 1926, Weiss was about to enter his headquarters, when a squad of hitmen opened fire from the windows of a nearby building’s second floor. Weiss was fatally injured, and died in the ambulance en route to the hospital.
16. The Chicago Outfit’s Feud With the North Side Gang Resulted in America’s Most Notorious Organized Crime Massacre
After Hymie Weiss was killed, his successor George “Bugs” Moran carried on the North Side Gang’s feud with Al Capone’s Chicago Outfit. The gangsters’ beef reached a crescendo on February 14, 1929, when seven members of the North Side Gang were stood up against a wall, then cut down by automatic weapons gunfire in what came to be known as the Valentine’s Day Massacre. It began when Capone hatched a plan to lure Moran to a warehouse, with the promise of a delivery of cut rate stolen whiskey, then kill him along with his chief lieutenants.
Just before he reached the warehouse, however, Moran spotted a police car approach the warehouse, and turned around. Four men in police uniforms exited the vehicle, entered the warehouse, and ordered its occupants to line up against a wall for a pat down. The cops were fake, and as soon as the men turned around to face the wall, the “policemen” opened fire with shotguns and Thompson submachine guns. Six died on the scene, and a seventh, who took fourteen bullets, refused to ID the shooters. He told investigators “nobody shot me”, before he expired.
15. The Feud Continued Even After the Valentine’s Day Massacre
Jack “Machine Gun” McGurn (1902 – 1936) got his nickname because of his love of Thompson submachine guns. He was a Sicilian born small time boxer, who changed his birth name from Vincenzo Gibaldi to the Irish-sounding Jack McGurn, because boxers with Irish names got better bookings back then. Boxing didn’t pan out, however, so McGurn put more time and effort into his criminal sideline as mob muscle. By the mid 1920s, he had become one of Al Capone’s chief bodyguards and hitmen. He was a suspect in the 1929 Valentine’s Day Massacre, but the authorities were unable to charge him for lack of evidence.
Because mob loyalty is largely a myth, Capone and the Chicago Outfit distanced themselves from McGurn to avoid the heat he drew as a suspect. Cast off, McGurn tried to become a professional golfer. He did no better than he had as a boxer, and fell into poverty. His misery came to an end on February 15, 1936, one day after the seventh anniversary of the massacre, when three hitmen shot him dead in a Chicago bowling alley. They reportedly left a Valentine’s card near McGurn’s corpse, that read: “You’ve lost your job, you’ve lost your dough, Your jewels and cars and handsome houses, But things could still be worse you know… At least you haven’t lost your trousers!”
The House of Plantagenet, which held the English throne from 1154 to 1485, was prone to infighting ever since the dynasty was founded. Indeed, the dynasty’s first king, Henry II, spent much of his reign locked into a feud with and at war against his wife and sons. The Plantagenets survived those earlier travails, but they failed survive another bout of intra-dynastic bloodletting, that began in the late fourteenth century. It was triggered by the tyrannical rule of King Richard II (1367 – 1400). Crowned at age ten, Richard had shown some promise early in his reign while still a teenager, when he suppressed England’s Peasants’ Revolt in 1381.
He did so with no small dose of nastiness, but a bit of nastiness was often a job requirement for medieval rulers. Richard became too nasty, however, and from a nasty teenager, he grew up to become a nasty customer as an adult. He proceeded to surround himself with corrupt officials, and ruled in an arbitrary and capricious manner. That triggered a rebellion led by many lords, including some of the king’s own Plantagenet relatives, who seized power. It was the start of England’s greatest family feud.
13. An Intra-Familial Squabble That Shaped English History
In 1386, King Richard II’s rebellious opponents formed a committee known as the Lords Appellant, which governed the realm and reduced the monarch to a figurehead. A Parliament, which became known as the “Merciless Parliament”, was called. It impeached several of the king’s favorites, confiscated their property, and ordered their execution. Richard bided his time, and as the years went by, he slowly rebuilt his power. Then in 1397, he struck back, reasserted his authority, and executed the most prominent Lords Appellant.
One of the king’s key opponents was Henry Bolingbroke, Richard’s cousin and the son of his uncle, John of Gaunt, 1st Duke of Lancaster. John of Gaunt had supported Richard and helped him regain power. He also acted as an intermediary between the king and his opponents, whose numbers included Gaunt’s own son. However, John of Gaunt died in 1399, and Richard decided to settle scores with his son. So he disinherited Henry Bolingbroke, declared him a traitor, and banished him for life. That only added fuel to the fire of the intra-Plantagenet family feud.
12. The Kingmaker Who Supercharged the Plantagenet Family Feud
The exiled Henry Bolingbroke did not stay in exile for long. He returned a few months after his banishment, raised a rebellion, and proceeded to defeat and depose his cousin. King Richard II was captured, and quietly murdered. Bolingbroke had himself crowned as King Henry IV, and founded the Lancastrian branch of the House of Plantagenet. The Lancastrians ruled England until the crown was disputed by the Yorkists – a Plantagenet branch descended from John of Gaunt’s younger brother Edmund, Duke of York – in the Wars of the Roses.
A key figure in the Wars of the Roses was Richard Neville, the 16th Earl of Warwick (1428 – 1471). Neville, the son of the powerful 5th Earl of Salisbury, also named Richard Neville, was a powerful nobleman in his own right. He demonstrated that he was a capable military commander during the intra-familial feud that erupted between the Yorkist and Lancastrian branches of the House of Plantagenet. He began the conflict on the Yorkist side, but then switched his support to the Lancastrians, and his role in the dethronement and enthronement of two kings got him nicknamed “The Kingmaker”.
11. The Fall of the Lancastrians and Rise of the Yorkists
The Wars of the Roses dragged on for 32 years from 1455 to 1487. They began when Richard, Duke of York, with the support of the powerful Neville family, made an attempt to seize the crown from his cousin, the feeble and mentally incapacitated King Henry VI. However, the attempt failed, and the Duke of York was slain in battle along with his ally Richard Neville, 5th Earl of Salisbury and the father of Richard Neville, the 16th Earl of Warwick.
The feud then passed on to the next generation of Yorkists, led by Warwick and the Duke of York’s son, Edward. Warwick was instrumental in securing victory for the Yorkists, who crushed the Lancastrians at the Battle of Towton in 1461. Henry VI was deposed and imprisoned, and his place was taken by the slain Duke of York’s son, who was crowned as King Edward IV. The new king was a great warrior, but was uninterested in government, so Warwick governed the realm on his behalf. It did not end well, and led to yet another twist in the family feud.
10. The Fall of the Yorkists and Restoration of the Lancastrians
The relationship between King Edward IV and his chief lieutenant Richard Neville, 16th Earl of Warwick, soured when Edward impulsively married a commoner. That ruined years of painstaking negotiations by Warwick for a treaty between England and France, which would have been sealed by Edward’s marriage to a French princess. Things came to a head in 1470 when Warwick, aided by King Edward’s younger brother, George Plantagenet, 1st Duke of Clarence – who had married Warwick’s daughter and thus became his son-in-law – deposed Edward.
The Yorkist king was forced to flee England, while the deposed Lancastrian King Henry VI was released from imprisonment, dusted off, and restored to the English throne. Warwick’s triumph was short lived, however: Edward returned to England in 1471, and raised a counter rebellion. At a critical moment, Warwick was betrayed by his son-in-law George, Duke of Clarence, who had a change of heart and defected back to his brother Edward. The two sides met in the Battle of Barnet on April 14, 1471, in which the Lancastrians were defeated and the Kingmaker was killed.
9. The Second Fall of the Lancastrians and Restoration of the Yorkists
Another and final Yorkist victory at the Battle of Tewkesbury, May 4, 1471, confirmed Edward IV’s restoration to the throne. The unfortunate Henry VI was deposed once again, and this time he was quietly murdered to eliminate the possibility of further trouble from Lancastrian loyalists. To be thorough, Henry VI’s only son, the teenaged Henry of Lancaster, was also killed. As to Edward IV’s wishy-washy brother George, Duke of Clarence, he continued to demonstrate his ingratitude to his elder brother. Understandably, that irked Edward IV, who had made George a duke in the first place, then made him Lord Lieutenant of Ireland at the age of thirteen.
That generosity was repaid with multiple conspiracies, and when the Duke of Clarence was caught in yet another plot, the exasperated Edward IV finally had enough. He imprisoned his younger brother in the Tower of London, tried him for treason, and personally conducted the prosecution before Parliament. George was convicted, attainted, and sentenced to death. On February 18, 1478, the 1st Duke of Clarence was executed by getting dunked into a big barrel of Malmsey wine, and forcibly held under until he was drowned. The Plantagenet family feud was not over, however.
8. An Usurpation That Opened Yet Another Chapter in the Intra-Plantagenet Family Feud
The Plantagenet family feud that had triggered the Wars of the Roses finally came to an end the afternoon of August 22, 1485, at the Battle of Bosworth. Its outcome was the result of one of history’s most momentous betrayals. The traitor was Thomas Stanley, 1st Earl of Derby (1435 – 1504). A powerful peer, Stanley had extensive landholdings in northwest England, and ran them as if they were an independent realm. Accordingly, his support was sought by both the Lancastrian and Yorkist branches of the House of Plantagenet as they vied for power.
The Yorkist King Edward IV had died of a sudden illness in 1483. Before he expired, he named his younger brother Richard, Duke of Gloucester, as regent to govern the realm during the minority of Edward’s twelve-year-old old son and successor, Edward V, and to act as guardian of the child king and his younger brother. However, Richard declared his brother’s sons illegitimate, and imprisoned his nephews in the Tower of London, where they disappeared and were likely murdered. He then had himself crowned as King Richard III.
The newly-crowned Yorkist King Richard III was almost immediately challenged by Henry Tudor, the last viable claimant of the defeated Lancastrian branch of the House of Plantagenet. After years of exile, Tudor returned to England in 1485 and declared his bid for the throne. Richard set out to meet his challenger at the head of his forces, which included a large contingent commanded by Thomas Stanley, 1st Earl of Derby. Stanley was a major Yorkist supporter, but he was conflicted. His family had been Lancastrians, but he himself had defected to the Yorkists, who handsomely rewarded him with lands and estates, and appointments to powerful government positions.
Stanley was thus deeply indebted to the Yorkists. However, he also happened to be married to Henry Tudor’s mother, and that made him the Lancastrian challenger’s stepfather. That stuck Stanley between the rock of loyalty, and the hard place of peace at home. So he decided to play both sides of the feud, and secretly contacted his stepson to explore defection. Things got complicated when King Richard got wind of that: he seized Stanley’s son as a hostage for his father’s good behavior, and an insurance against treachery. He then ordered Stanley to join the Yorkist army with his contingent, which the earl reluctantly did.
King Richard III and Henry Tudor met at the Battle of Bosworth on August 22nd, 1485, but the king’s reluctant ally, Thomas Stanley, was still undecided. So he kept his armed contingent to one side of field, and waited to see who looked like a winner. Richard sent Stanley a message that ordered him to immediately attack the Lancastrians, and threatened to execute his son if he did not. The earl coolly replied: “Sire, I have other sons“. A livid Richard ordered the execution of Stanley’s son, but the order was not immediately carried out, and before long, it was too late. As the afternoon wore on, Stanley made up his mind that Richard was losing the battle, so he ordered an attack – against Richard and the Yorkist forces.
Stanley’s betrayal decisively tipped the scales in favor of Henry Tudor, and against Richard III. The king launched a fierce attack in a desperate attempt to reach and cut down his rival, but was cut down himself. After Richard’s death, Stanley found his fallen crown in some bushes, and personally placed it on the head of Henry Tudor, henceforth King Henry VII. Stanley’s stepson and new king of England brought the intra-Plantagenet feud to end when he ended the Plantagenet dynasty, and replaced it with his own House of Tudor. As to Stanley, treachery paid well, and he was handsomely rewarded by his son in law for his betrayal of King Richard.
5. The Mob Feud That Triggered the Italian-American Mafia’s Most Infamous Gang War
Throughout much of Prohibition, the Italian-American mafia was led by rivals Joe “The Boss” Masseria and Salvatore Maranzano. Years of mounting tensions between their criminal organizations finally exploded into a bloody struggle that came to be known as The Castellammarese War, from February, 1930, until April, 1931. Masseria had been America’s dominant Mafiosi in the 1920s. He ran a powerful crime family whose ranks included future mob bosses such as Charles “Lucky” Luciano, Vito Genovese, and Frank Costello. However, a Don Vito Ferro, a mafia chieftain from Castellammare del Golfo, Sicily, decided to reach out and wrest control of the American mafia. To that end, Ferro sent Salvatore Maranzano to establish the rival Castellammarese faction.
The Castellammarese included future bosses such as Joe Profaci, Joe Bonano, and Stefano Maggadino. In 1928, the factions began to hijack each other’s alcohol trucks and otherwise encroach upon and disrupt their rival’s bootlegging operations. The struggle broke out into the open in February, 1930, when Masseria had a Castellammarese Detroit racketeer killed. The Castellammarese retaliated a few months later with the murder of a key Masseria enforcer in Harlem. A few weeks later, they got a Masseria ally whom he had earlier betrayed, the Reina family, to switch sides, and kill a key Masseria loyalist on their way out. Masseria responded in October, 1930, when he sent one of his key lieutenants, Alfred Mineo, to kill a key Castellammarese ally, Joe Aiello, in Chicago.
4. The End of This Feud Led to a New Beginning for the American Mafia
In November, 1930, Alfred Mineo and another key Masseria henchman were murdered, and Mineo’s successor defected to Salvatore Maranzano. The tide then swiftly turned, and other Masseria allies switched allegiance to the Castellammarese. Masseria’s remaining key henchmen, led by Lucky Luciano, realized that their boss’s ship was about to sink. So Luciano approached Maranzano, and offered to defect and seal the deal with the murder of Masseria, who was duly rubbed out on April 15th, 1931. Maranzano then reorganized the Italian-American mafia, and set up the basic structure that survives to this day of made soldiers who answer to captains, who in turn answer to a family underboss and boss.
However, Maranazano, an egomaniac with delusions of grandeur who fancied himself a Julius Caesar of the criminal world, did not enjoy his victory for long. Five months after Maranzano declared himself capo di tutti capi, or Boss of All Bosses, Lucky Luciano had him murdered. He then abolished the Boss of All Bosses title, and set up a collective mafia leadership council to avoid future gang wars. On the surface, the Castellammarese War had been a power struggle between Masseria and Maranzano. An underlying current of the feud, however, was a generational struggle. Younger underlings, who grew up American, resented the rival bosses and their entire generation of leadership – derided as “Mustache Petes”. They saw them as insular, set in their Old World ways, and unwilling or unable to adapt to American realities.
The Hatfield and McCoy Feud, a protracted nineteenth century vendetta between neighboring clans along the border between Kentucky and West Virginia, is America’s most infamous family feud. Fought largely in the 1880s, it pitted the McCoys, most of whom lived in Pike County, KY, against the Hatfields, who lived mostly in neighboring Logan County, WV. The bad blood between the rival clans led to significant violence, mayhem, and murder. As modern science and research have revealed, and as seen below, there was literal bad blood that drove and amplified the vendetta.
The McCoys were led by Randolph “Old Ran’l” McCoy, while the rival Hatfields were led by William Anderson “Devil Anse” Hatfield. The earliest known violence dates to 1865, when Harmon McCoy, a Union Army veteran who had fought in the US Civil War, was murdered by a band of Confederate guerrillas led by Devil Anse Hatfield. Bushwhacking had been common throughout the conflict, so the killing did not lead to an immediate feud. However, it stored hard feelings for later on down the road.
In 1878, a McCoy accused a Hatfield of stealing a hog. The Hatfield was acquitted, but one of the witnesses who took his side was murdered by the McCoys in retaliation soon thereafter. Tensions increased in 1880, when Devil Anse Hatfield’s son impregnated Old Ran’l McCoy’s daughter. Then in 1882, Devil Anse’s brother was mortally wounded in a brawl with three McCoys over a small debt owed on a fiddle. The Hatfields retaliated with the capture and execution of three McCoys. That was when things exploded into a prolonged back forth vendetta.
Things got bad not just for the immediate clans involved, but for outsiders, who felt the ripple effect of the feud. At times, the beef between the two families threatened to turn into a war between the states of Kentucky and West Virginia. By 1890 the Hatfields, who had seriously gone overboard in the brutalities during the course of the vendetta, had been reduced to homeless hunted fugitives. Finally, four of them, plus their accomplices, were arrested and indicted for one particularly heinous atrocity.
The fighting between the Hatfields and McCoys finally came to an end in February, 1890, when Ellison “Cottontop” Mounts, a Hatfield, was hanged in Pikesville. The feud was remarkable for its intensity and longevity. That ability to keep a good hate going for a long time might have been due – at least on the McCoys’ part – to genetics. In 2007, an eleven-year-old McCoy girl prone to fits of rage underwent medical tests to find out just what was wrong with her. It was discovered that she, and many members of the McCoy clan, had tumors on their adrenal glands.
According to doctors, those kinds of tumors can cause the release of massive amounts of mood-altering chemicals, such as adrenalin. That could explain much about the infamous feud. As the McCoy girl’s physician put it, her family’s genetic defect: “does produce hypertension, headache and sweating intermittently depending on when the surge of these compounds occurs in the bloodstream. I suppose these compounds could possibly make somebody very angry and upset for no good reason“. Feuding was literally in the McCoys’ blood.
Where Did We Find This Stuff? Some Sources and Further Reading