Tag Archives: Mob

HOW AL CAPONE CRIMINALLY CAPTURED CHICAGO

Al Capone. The name signifies ultimate dominance in the Prohibition-era American underworld. Capone, aka “Scarface” (a nickname he loathed), grew to rule Chicago’s gangsters as well as overlording many police officers and public officials. And he did so while in his twenties, before hubris took him down through tax evasion—not murder, extortion, robbery, drug trafficking, racketeering, prostitution, gambling, and his running over a thousand illegal speakeasies. Being crime’s kingpin was a mighty accomplishment for a man so young, and there are two primary reasons for how Al Capone criminally captured Chicago.

Al Capone was a true anti-social mastermind. He was a sadistic savage who used brute force to achieve his ends, and he masterfully manipulated others to do his murderous bidding. “Big Al” (he stood 5’10” and weighed 260 lbs.) was also a master strategist who intrinsically knew the flaws in human nature—greed and fear—and how to take an entire city under his control.

Capone ran Chicago’s underworld from the mid-1920s to his removal through financial conviction in 1931. During that time, when Chicago’s population was slightly over three million, the city experienced nearly one thousand gangland murders. Many, including the infamous St. Valentine’s Day Massacre, were ordered by Al Capone.

Before analyzing Al Capone’s colossal success and spectacular failure as well as identifying two primary reasons for how he captured Chicago, let’s look at who Al Capone was and how he became America’s most notorious gangster.

Alphonse Gabriel Capone was born in Brooklyn, New York on January 17, 1899. His parents were immigrants from the Italian Province of Salerno—his father was a barber and his mother a seamstress. Al Capone had eight siblings; two brothers going into law enforcement and two other brothers eventually taking roles in his criminal enterprise.

Capone was expelled from school at age 14 after assaulting a female teacher. He’d punched her in the face when she tried to discipline him for aggressive behavior. He then worked at odd jobs in New York City such as a candy store clerk, a bowling pin boy, an ammunition plant laborer, and a bookbinding cutter. But he found his calling at eighteen when he was hired as a barroom and brothel bouncer.

Al Capone was a large kid—a tough kid with a quick temper and a deeply ingrained mean streak. On the surface, though, Capone was charming, witty, and unusually clever. This character combination aligned him with one of New York’s leading criminals, Johnny Torrio.

It was in one of Torrio’s bars that Al Capone earned his nickname “Scarface”. A punk hoodlum called Frank Galluccio slashed Capone across the left side of his face leaving two huge gashes. Capone had insulted Galluccio’s sister which set off the fight. Capone was scarred for life, and he thereafter consciously avoided having himself photographed from the left.

Capone rose in the New York criminal culture. It was partly through Torrio’s influence and partly due to Capone’s natural ability to thrive in the underworld. It led to a move to Chicago.

Johnny Torrio was invited to partner with “Big Jim” Colosimo who headed the Chicago Outfit that operated in the Cicero suburb of west-central Chicago. Colosimo’s territory was constantly threatened by the North Side Gang run by the powerful Dean O’Banion who was supported by the infamous henchmen Bugsy Moran, Hymie Weiss, and Vincent Drucci. It was the eventual and ongoing rivalry between the Chicago Outfit and the North End Gang that caused most of the gangland hits.

Colosimo needed Capone’s muscle, and he needed Torrio’s brains. They created a symbiotic relationship, but there was one main problem. Colosimo was an old-school man. He approved of robbery, extortion, gambling, prostitution, and, of course, murder. But he was a pro-prohibitioner who disapproved of alcohol.

Torrio and Capone saw Prohibition as a gold mine. They saw Chicago as an untapped opportunity to make enormous profits by cornering the illegal booze manufacturing and delivery market. Colosimo, the boss, didn’t see it that way and had no plans to expand his enterprise into the bootlegging business.

On May 11, 1920, Big Jim Colosimo was shot dead as he went to a restaurant meeting with Johnny Torrio. History suspects Al Capone ordered the hit with Johnny Torrio’s blessing, but history shows Capone was conveniently in New York at the time. Regardless, Colosimo’s death allowed Torrio to take control of the Chicago Outfit with Capone as his right-hand man.

That arrangement lasted long enough for the Chicago Outfit to gain its upper hand in the illegal liquor business. Torrio and Capone made strong ties with Canadian alcohol manufacturers as Canada had no Prohibition rules whereas the US Act prohibited the manufacturing, distribution, and sale of all “recreational” liquor products. It was not illegal to possess or consume alcoholic beverages in the States—only to make and move them.

Tensions grew between the Chicago Outfit and Dean O’Banion’s North End Gang. On November 10, 1924, the Torrio/Capone alliance murdered O’Banion. In retaliation, the North Enders ambushed Johnny Torrio and wounded him so badly that Torrio resigned as head of the Outfit and returned to New York. This left Al Capone solely in charge and the gang violence quickly escalated.

Capone implemented every fear and intimidation tactic he could to eliminate his underworld rivals and force purchasing compliance on his marketplace. Capone’s loyal goons’ favorite weapon was the Thompson .45 submachine gun with 50-round magazines—the Chicago Typewriter, it was called. Capone sent multiple squads of gunmen after his targets, often shooting hundreds of bullets into buildings and passing cars.

One by one, Capone eliminated criminals like Hymie Weiss and Vincent Drucci. But a certain high-value hit, Bugsy Moran, played hard to get. This is when Capone set up the Saint Valentine’s Day Massacre in 1929. Capone’s men, three dressed in police uniforms, raided a Chicago garage where the North End Gang was holding a clandestine meeting. The men under Capone lined seven North Enders up against a brick wall and mowed them down with machine gun fire.

By sheer coincidence, good or bad luck depending on how you see it, Bugsy Moran was late for the meet and survived. However, with his gang decimated and his power weakened, Moran gave up and left the Chicago mob scene. This left Capone as the kingpin, except for a side rivalry.

In 1925, as Capone was ascending in Chicago’s crime hierarchy, he meddled in the Unione Siciliana which was a Sicilian-American benevolent society—a convenient place for money laundering. Capone deposed Joe Aiello as head of the society and replaced him with a Capone hack called Antinio Lombardo. This infuriated Aiello, and he made it his personal mission to take Al Capone out.

From this point forward, despite the North End threat, Capone lived under constant fear of being assassinated. He beefed up security by having fortified residences, hoards of bodyguards, a bulletproof limousine, and unpredictable travel habits. Capone began spending more time away from Chicago, buying a mansion in Florida and laying low in Las Vegas.

Rumors were that Al Capone had hideouts in Canada despite Capone’s famous quote, “I don’t even know what street Canada is on.” Moose Jaw in Saskatchewan claims fame for the “Capone Tunnels” under its city. So do places like London, Ontario, and Windsor across the river from Detroit.

While Aiello went after Capone, so did the Revenuers. Until the St. Valentine’s Day Massacre, Al Capone was nearly untouchable in Chicago. Although Capone instilled mortal fear into his rivals, he had immense popularity with Chicagoans. Not only did the drinking public love Al Capone, so did the cops, the courts, and the civic authorities.

Capone played to the common greed as well as the common fear—two ingrained human condition frailties. He had hundreds, if not thousands, of people across the spectrum on his protection payroll. This included police at the patrol level as well as in high administration positions. He had the mayor in his pocket, the DA at his side, and enough goods on judges which forced them to hold his line.

The Roaring Twenties in Chicago was a time when law enforcement and the judiciary were pretty much of a joke. Officers were severely underpaid. Many had second jobs to make ends meet so they were wide open to bribes. So were politicians who appointed the court staff.

Capone knew he could intimidate enemies with the fear of brutal terror, and he knew he could buy his way to having greedy officials look the other way. He also knew he could purchase the hearts and minds of the common people with donations to churches, food pantries for the poor, housing for the displaced, funding for orphanages, and pensions for widows.

To most of the overlooking public, Al Capone was not a gangster. He was a successful businessman—a guy you’d like to have drinks around the pool with—who supplied liquor to a majority who hated Prohibition and viewed the law as wrong. Leave Al alone was the thinking. All he was doing was supplying entertainment to the city. Getting witnesses to testify against him was nearly impossible.

February 14, 1929, was a turning point in Capone’s criminal career. The tide of public support turned from this outrage in violence. Walter A. Strong, publisher of the Chicago Daily, turned to his good friend, newly inaugurated President Herbert Hoover for help to smash Capone and the Chicago Outfit. As Hoover recorded in his memoirs:

“Walter Strong made an argument that Chicago was in the hands of the gangsters, that the police and magistrates were completely under their control… that the Federal government was the only force by which the city’s ability to govern itself could be restored. At once I directed that all the Federal agencies concentrate on Mr. Capone and his allies.”

A second movement went against Al Capone. On March 24, 1930, Capone’s face appeared on the cover of Time Magazine. The caption and story weren’t flattering. On April 23, The Chicago Crime Commission issued its first Public Enemies List. There were 28 names on it and Al Capone was in first place, He became Public Enemy #1.

1929 wasn’t kind to Al Capone. Neither was 1931. Here’s a summary of Capone’s downfall:

March 27, 1929 — Capone was arrested outside a Chicago courthouse for contempt of court.

May 16, 1929 — Capone was arrested in Philadelphia on weapons charges.

May 17, 1929 — Capone plead guilty to the weapons charges with a plea deal. He received a one-year sentence that was served in an open prison setting.

An intense investigation into Capone’s finances was conducted in 1930.

March 13, 1931 — Capone was charged with income tax evasion for the year 1924.

June 5, 1931 — Capone was indicted on 22 counts of federal tax evasion for the years 1925 through 1929.

June 16, 1931 — Capone’s lawyers and the prosecution worked a plea deal to one single count of tax evasion. The judge refused to allow it. All counts went to trial.

October 17, 1931 — A jury convicted Capone on 5 counts of tax evasion. He was sentenced to 11 years in prison, fined $50,000, assessed court costs of $7,692, and made subject to $215,000 in interest due on back charges.

The prosecution proved a case that Capone’s traceable income was $1,038,654 from 1924 to 1929. The real amount was likely much higher. Some investigators estimated it to be $100 million which in 2023 inflated value is $1.7 billion.

Al Capone went straight from trial to jail. First, he was incarcerated in the U.S. Penitentiary, Atlanta. In 1934, Capone was transferred to Alcatraz Island in San Francisco Bay. He stayed there until 1939 when he was paroled due to medical conditions.

Capone suffered from an untreated syphilis infection which ate away his brain. He was nearly non-functional when he returned to his Florida residence. He lingered on in an invalid state until he died of heart failure on January 25, 1947. Al Capone was buried just outside Chicago and in the Capone family plot.

This post opened by stating there were two primary reasons for how Al Capone criminally captured Chicago. They’ve been mentioned throughout the text, but there are many supporting characteristics to Al Capone’s character that allowed him to achieve his power. Here’s a few of them:

Charisma and Leadership — Capone possessed a commanding personality—highly energized, witty, yet serious. He inspired loyalty among his associates and maintained discipline throughout his organization.

Outstanding Presence — Al Capone was meticulous in appearance. Clean-shaven, short hair, impeccable suits, shirts, and ties, with perfectly polished shoes. He knew how important turnout was for respect, and he demanded the same professional look in his men.

Strategic Mindset — He was a shrewd businessman who saw opportunities, weighed risks, and focussed on reward. One of these was the immense opportunity offered him through the Act of Prohibition.

Adaptability — Capone was quick to change tactics when necessary. He understood the concepts of overall strategy supported by flexible tactics.

Exploiting the Civic Environment — Capone instinctively realized how malleable humans are. He knew most folks, public, private, and civil officials, naturally take an easy route out when offered a choice.

Corruption and Political Ties — He and his gang infiltrated the highest levels of Chicago’s political circles. He exploited them through bribery, blackmail, threats, and rewards that were impossible to refuse.

Community Support — At the street level, those who weren’t terrified of Al Capone worshipped him. He was instrumental in supplying the common person with the basic securities and necessities of life.

Absolute Ruthlessness — Those who opposed or crossed Capone ended up dead. And not dead by nice means. Capone had his enemies tortured, maimed, and exterminated in horrible ways… and the word got around.

If Capone had put his intelligence, organizational skills, and drive toward legitimate purposes, there’s no telling what he might have achieved. But he didn’t. It was the nature of this beast to be a bullying antisocial reprobate. He thrived knowing humans primarily respond out of greed and out of fear. He played to those flaws, and that is how Al Capone criminally captured Chicago.

KUDOS TO WHOEVER WHACKED GANGSTER JAMES “WHITEY” BULGER

One of the world’s most infamous criminals is dead. 89-year-old James Joseph Bulger, aka Whitey—once head of the Boston Mob—was murdered inside Hazelton Federal Penitentiary in West Virginia on October 30, 2018. Authorities transferred Bulger from a Florida maximum security jail to the WV medium security facility less than 12 hours earlier. The wheelchair-bound, high-risk geriatric inmate got placed in general population. Credible prison sources say other prisoners quickly isolated and beat Bulger beyond recognition using the “lock-in-a-sock” technique, tearing his eyes from their sockets and cutting out his tongue. It was a signature end for the notorious American gangster.

Whitey Bulger was more than a larger-than-life mobster—he was a devious, double-crossing sonofabitch convicted of eleven brutally cruel murders inflicted on organized criminal associates during the 70s and 80s when South Boston’s Irish Mob ruled town. Bulger also acted as a top FBI informant and turned into a Bureau embarrassment while he continued his criminal enterprise under federal government immunity. Just before indictment on racketeering charges, Bulger’s FBI handler tipped him off. That corrupt information about pending arrest gave Bulger years on the lam before he was taken down in 2011.

My opinion is Whitey Bulger deserved what he got, and kudos to whoever whacked him. It was long overdue. Bulger should have been executed years earlier had the State of Massachusetts retained the death penalty and nabbed him. However, his murder inside the joint raises the question of what protection a high-profile and vulnerable prison inmate like Whitey Bulger is entitled to.

That Bulger died less than a day after arrival at Hazelton suggests powers within the U.S. Bureau of Prisons intentionally placed Bulger in peril. It’s likely no coincidence convicted Boston mafia hitman, Fotios “Freddy” Geas, was on the scene and in the cell when Bulger died. Currently, Freddy sits on ice. He’s in the hole pending an investigation.

Before examining who in the system is accountable for setting up an old con-man’s death, let’s look at Bulger’s past and what he did as a sociopathic killer.

James Bulger was born in 1929 at Everett in North Boston. His father was injured in an accident and unable to work, placing the family in poverty. From an early age, James Bulger bounced between relatives’ homes and whoever would put up with his delinquent behavior. Nicknamed “Whitey” for his platinum hair, Bulger preferred being called “Jimmy”. However, the name Whitey stuck and it stayed with him throughout his criminal career.

Whitey Bulger developed a nasty reputation as a cruel dude. At fourteen, he was a seasoned street fighter and enforcer for the South Boston Shamrock gang. Also at fourteen, Bulger went to jail for theft and burglary. He was placed in adult population and learned from some of the country’s most experienced cons.

Bulger was in and out of prison during the war years. He tried reforming in 1948 by joining the U. S. Air Force, but that didn’t work. Whitey Bulger was jailed in military prison for assaults and being absent without leave. To get rid of Bulger, the Air Force released him with an honorable discharge in 1952. He went back to the streets of South Boston.

Whitey Bulger graduated to extortions, drug trafficking and armed robberies. By 1956, he was incarcerated for robbery in Atlanta but was transferred to Alcatraz prison at San Francisco. Bulger was too much for Alcatraz authorities to handle so they sent him to the super-maximum pen at Leavenworth. He made parole in 1965 and never saw another day in jail for 46 years.

Back in Boston, Whitey Bulger joined the Killeen gang who were established pimps and bookies as well as experienced loan sharks and bone bashers. During a gang war between the Killeens and their rival Mullen gang, Bulger committed his first known murder by shooting an unarmed man between the eyes, then biting off the end of his nose. Things heated up for the Killeens and Bulger, so he turn-coated to the powerful South Boston mob. Bulger joined the Winter Hill gang and went about setting up the Killeens to eliminate their leaders.

Whitey Bulger rapidly rose in South Boston’s underworld. He had a peculiar modus operandi, or MO, for a con. Bulger preyed only on other criminals, not the general public. It was a pattern that worked well for Bulger, as it was high-level criminals who controlled the money, and he used the lower lying cons to rat out their bosses.

Whitey Bulger manipulated other influential people, too. He was a paid informant for the Boston Police and given leeway to operate with impunity. Bulger worked both ends against the middle. By the mid-70s, Whitey Bulger was in complete control of the South Boston mob. Secretly, he was also the FBI’s snitch.

In 1971, the FBI recruited Whitey Bulger. Or, it was more like Bulger recruited the FBI. What Whitey Bulger wanted was the FBI’s help in eliminating the Italian Mafia while leaving him alone, and it worked. Soon Mafioso members were being rounded up and jailed. Other Bulger rivals were disappearing or turning up dead. Throughout the 1980’s, Whitey Bulger ran unopposed and committed or ordered at least nineteen known murders. His body count might be higher.

There was a problem, though. That was Bulger’s FBI handler, Special Agent John Connolly who’d been giving Bulger carte blanche permission to operate freely as long as Connolly got arrests. Connolly was eventually exposed by the Bureau as a crooked cop, but not before tipping Whitey Bulger off that a Racketeer Influenced and Corrupt Organizations Act (RICO) indictment was about to fall on Bulger’s head.

With FBI Agent Connolly’s help, Whitey Bulger went into hiding. This was in 1994. For the next seventeen years, Bulger was a wanted man, and for twelve of them, Bulger was on the FBI’s most wanted list at #2—right behind Osama bin Laden. A $2 million reward was offered for Bulger’s scalp and sightings came in all over the world.

But the truth was, Whitey Bulger never left the States. He and his long-time girlfriend, Catherine Greig, holed-up in California where they rented a quiet apartment in Santa Monica. Finally, after the FBI did a media blitz with age-corrected sketches of Bulger and Greig, a neighbor recognized the pair and turned them in.

It was June 22, 2011, when the police captured Whitey Bulger. He was now 81. In Bulger’s apartment, they seized over $800,000 cash and a horde of firearms along with plenty of fake ID. Bulger and Greig were extradited back to Massachusetts where Grieg pleaded guilty to harboring a fugitive. She drew six years. Bulger went to trial.

Whitey Bulger was charged with 48 felony counts—19 of them first-degree murders. The trial lasted three months and heard from a rogue’s gallery of convicted mafia members, mobsters and hitmen. It also heard from relatives of Bulger’s victims. The jury convicted Bulger on 11 murders, and he was sentenced to two consecutive life terms, plus an extra five years for good measure.

Evidence told of Bulger’s viciousness. He had many people severely tortured, especially those suspected of informing on him. Some of those maimed and then killed were women—girlfriends of Bulger’s subordinates in the gang world. Others were rival drug dealers and racketeers who posed business threats to Whitey Bulger. Further evidence showed Bulger being involved with arms trafficking to the Irish Republican Army terrorist group as well as firebombing Senator Ted Kennedy’s house.

Upon sentencing Whitey Bulger, Judge Denise Casper told him, “The scope, the callousness, the depravity of your crimes are almost unfathomable. Your crimes are more than heinous because they were all about money.” Bulger replied, “Money is the common denominator in crime. It will never stop.” Bulger also said he wanted an epitaph on his tombstone stating, “I’d rather be in Alcatraz.”

*   *   *

Whitey Bulger was also indicted for murders in Florida and Oklahoma, however, prosecutors there stayed charges due to his age and existing life sentences. Bulger first went to the Coleman II U.S. Penitentiary in Somerville, Florida where he was held in protective custody. Later, he moved to the Federal Transfer Center in Oklahoma City, also in protective custody, then back to Florida. All of Bulger’s federal pen time from 2014 till 2018 was in maximum security and tight protection—never given access to the general inmate population. Even though he was old, Whitey Bulger was a marked man and a high-value target inside the system.

Then, on October 29, 2018, Bulger was suddenly transferred from protective custody in a Florida max jail to open population at a medium place in West Virginia. He arrived at 9:53 pm and by 8:20 the next morning, Whitey Bulger was whacked in his cell. Conveniently, the cameras didn’t catch the actual death sentence, and somehow Freddy Geas and friends were lying in wait. This reeks of a system-orchestrated event.

When I say kudos to whoever whacked Whitey Bulger, you might think I’m condoning planned and premeditated murder. I’m not—not for ordinary, law-abiding and peaceful citizens that is. But, I’ve got no sympathy for the devil, and I think guys like Whitey Bulger, Freddy Geas and their kind deserve what they get in the end. Career criminals are not remotely like you and me. These animals have no regard for human rights and human life. It’s the law of the jungle in their world, and it’s fitting that Whitey Bulger finally got whacked.

But, what I’m having a hard time getting my head around is how bureaucrats and employees in the correctional system stuck their necks out like this. I’ve been around the system for decades and I know most system players are government appointees and employees. They value security, promotions, pensions and non-publicity. Yet, somebody—some people—within the United States Bureau of Prisons let Whitey Bulger’s murder happen.

This case made the news. There’s a fascination with gangster and gang lifestyles in America and around the world. Whitey Bulger was a pop-figure and a cult idol. Just look at two high-profile movies like The Departed where Jack Nicholson won an Oscar portraying Bulger’s character. Then Johnny Depp hit the big screen as Bulger in Black Mass. Currently, there’s a lot on the news about Whitey Bulger.

I found an interesting interview in the Washington Post with retired Boston PD Sergeant Bill Bratton. He knew Whitey Bulger and described him as, “The consummate gangster. The consummate manipulator. He was a brutal, feared, stone-cold killer.” Another cop, not wanting to be identified, simply said, “He was a bad, bad, bad guy.”

Although it’s interesting to hear comments about Bulger’s character, I was more curious about how people in the correctional system responded. I found an answer through NBC where Rick Heldreth agreed to a statement. Heldreth is president of AFGE Local 420 Prison Workers Union representing employees at Hazelton Penitentiary in West Virginia. Here’s how Rick Heldreth explained it.

“Hazelton is known as one of the most violent penitentiaries in the country. It’s very unusual that this particular inmate (Bulger) of this notoriety would be placed in general population given the level of violence and the type of inmates housed here. This decision was made far above us. Hazelton has a reputation of con-honor and placing a massive turncoat like him (Bulger) in general population and not in protective custody made him particularly vulnerable to attack. I know how he was labeled in the system, and it’s not something that went well with our inmate population.”

Rick Heldreth offered insight about how recent federal government cutbacks affected their staffing levels. Heldreth reported that Hazelton normally holds 120 high-profile, violent inmates. It’s one of the most dangerous environments in America’s prison system. In the past three months, there were two other inmate murders, both happening immediately after admission. Heldreth said inmates always know who’s coming in. “It’s really like in the movies.”

Heldreth stated it takes 880 staff to manage 120 inmates at Hazelton. That’s a 7.3:1 ratio. “Since the Trump-era hiring freeze, we’re down about one hundred staff and can’t replace them. We have prison plumbers and teachers filling in for guards.”

In my opinion, forces within the U.S. Bureau of Prisons purposely sent Whitey Bulger to his death at Hazelton Penitentiary. Bulger was far from a model prisoner. He was a problem—a psychopath and without any form of normal conscience. Shortly before being sent to Hazelton, Bulger’s file records that he masturbated in front of a female prison worker and—at 89—threatened to kill another prison official. They had enough of him.

We’re not in a perfect world. If we were, Whitey Bulgers wouldn’t exist. But they do, and now one of them got a just reward. I say kudos to whoever whacked Whitey Bulger. He was fair game after prison authorities threw fresh meat over the fence and into the jungle. But autonomous authorities shouldn’t authorize death sentences and capital punishment really has to follow a legal and due process.