Saturday, August 30, 2025

In The Shadow of White Hats


With His Hearty "Hi-yo Silver"
The Lone Ranger

In The Shadow of White Hats

        As a young boy growing up in Connecticut, I tore 
through the neighborhood with a holstered cap pistol on my hip, playing cowboys like every other kid on the block.  My favorites, Hopalong Cassidy, the masked Lone Ranger, and Roy Rogers, rode in from the TV screen wearing white hats, dispensing noble justice to become my superheroes.  What we didn’t realize back then was that, not long before, even the so-called “bad guys” had their turn wearing white hats—at least for a moment.

Years later, after watching all 86 episodes of The Sopranos, I began to understand how layered and nuanced the world of “bad guys” could be.  Morality wasn’t a straight line but more like a seesaw.  There were gradations of villainy, shades of gray on a spectrum most of us assumed was strictly black and white.  Dante himself imagined nine levels in the inferno of Hell to account for the complexity of human sin.  Why not television?

 Tony Soprano, the Italian-American mob boss at the center of the show, often seemed to teeter on

'Good Guy' Paolo with Sister


this seesaw of morality.  He was ruthless one moment, oddly endearing the next.  Despite his violent profession, you could almost root for him as he tried awkwardly, sometimes sincerely, to reconcile his role as a father and husband with his life as a mafia capo, entangled in a world of strict codes, unspeakable crimes, and tangled loyalties. [2]

Like many real-life mobsters, Tony lived by a code that put the Cosa Nostra above all else. [2]  And yet, history holds an odd footnote: during World War II, some of America’s most notorious criminals aided the US war effort—at home and abroad—in one of the most unlikely alliances between the Italian-American Mafia and the US Government. 

On a sunlit afternoon in Malta, Maria Elena and I wandered the Barrakka Gardens, once the exclusive haunt of the Knights of St. John.  We paused

Strolling the Barrakka Gardens, Valletta, Malta

for cold drinks, then watched the booming salute at the Saluting Battery overlooking Grand Harbor.  Unawares, we had no idea what lay beneath our feet until Maria Elena and I entered the Lascaris subterranean complex, a warren of tunnels carved centuries before, used during the Crusades, and later transformed into the nerve center for Operation Husky, the 1943 Allied invasion of Sicily. [1]  In these war rooms, we learned of the unlikely alliance that evolved to support Operation Husky, which on 10 July 1943, saw 2,500 Allied warships poised off

Booming Cannon Salute


the coast of Sicily, prepared for the largest amphibious invasion yet attempted in World War II. 

Inside the Lascaris labyrinth, generals and strategists had pored over maps as battle plans were drawn.  Among the usual wartime memorabilia and charts, one poster stopped me cold:  Was this Charles “Lucky” Luciano, America’s infamous emperor of vice?  What on earth was he doing here?  At first, I thought I was mistaken; surely it couldn’t be Luciano.  I was wrong.  Reading it, of all people, of all places, I was introduced to this nefarious mob boss and, to our surprise, once a quiet asset of the United States Government.  His

Maria Elena Entering the 
Lascaris Headquarters Complex

participation in the war occurred while he languished in a New York prison on vice charges.  What had gone on here?  This was a “Bad Guy” who, beyond sporting a black hat, should have dressed totally in black.

The answer began in February 1942, when the pride of the French fleet, SS Normandie, caught fire and capsized at Manhattan’s Pier 88. [3]  Had it really been an accidental fire sparked by a torch, or was that a cover story?  The cause was never proved.  Overnight, whispers of Nazi infiltration and sabotage swept the docks.  The loss was a shocking disaster: captured from the Vichy French Government, the ship could have carried 10,000 troops across the Atlantic in four days, but now lay on her side in the Hudson River, a twisted, smoking carcass.  Rumors of Nazi sabotage along US eastern ports quickly spread.  Had someone on the docks fed the Nazis information?  Only the mob that controlled the docks had the

A Stratling Discovery

power to hunt down the guilty party. [3]  

The United States Navy, specifically the Office of Naval Intelligence (ONI), had few ways to police the sprawling New York waterfront, let alone the entire eastern seaboard.  But one organization did: the Italian-American Mafia.[1]  To secure the docks from further losses, the ONI, which held strong reservations about an alliance with the Mafia, was ordered to secretly team with the NYC Mafia, organized crime of Italian and Sicilian heritage, to help secure the docks.  The Mafia represented the most antifascist organization in the world, but in this strange mix, could such a notorious criminal organization be trusted? [1]  Likewise, would organized

Gallery Overlooking Lascaris Plotting
Room With Sicily Map Front & Center

crime see the Navy as a threat?  In a pact sparked by a fire, each side saw the other as the devil. [3] 

It was a cautious beginning.  Luciano was leery of cooperating and initially hesitated.  The Navy hadn’t offered a reduction in his sentence, and as an illegal alien, the mobster faced deportation.  Despite these realities, his grip on power was slipping.  To his advantage, the proposal provided him with cover to communicate with his lieutenants and maintain power.  True to his nickname, “Lucky,” he emerged as the Mafia point man after the Navy quietly held meetings with the underworld boss.  It was a gamble.  With a possibility of winning more than losing, Lucky took

Charles 'Lucky' Lucino

it.  At that moment, ‘Operation Underworld,’ a rather undisguised name for a covert operation, truly kicked off.

From exile at Great Meadow Penitentiary, Lucky tapped Meyer Lansky, known as “The Little Man,” a Jewish mobster, patriot, and fierce opponent of fascism.  As a staunch Zionist and extremely patriotic American, he’d oversee the entire operation as Lucky’s eyes, ears, and mouth on the outside.  Long before the declaration of war, Lansky already had a history of roughing up the pro-Nazi German-American Bund, sending his men to break up rallies and to battle brownshirt sympathizers in Manhattan streets. [3]

Lansky’s strong hand quickly solved the problem for the Navy on the waterfront by the visible deployment of some of the most ruthless gangsters in the city. [1]  From 1942 onward, mob heavies came and went from the Navy’s suites in New York’s elegant Astoria Hotel. [3]  From there, mob intermediaries relayed orders from Naval Intelligence to the gangsters controlling the longshoremen’s unions to carry out anti-Axis missions. 

Their influence over the longshoremen’s unions

Project Underworld Headquarters,
Hotel Astoria, Times Square, NYC 

and waterfront labor rackets prevented strikes, limited theft of vital war supplies by black marketeers, and aided in countering Axis spies and saboteurs.  The Mafia supplied intelligence ranging from dock activity, coastal submarine sightings, and the resupply of German U-boats operating off the US East Coast by sympathizers. [1]  Under their watchful gaze and heavy-handedness, not a single act of sabotage, labor strike, or suspicious fire occurred for the rest of the war. [3]

This cooperative effort of strange bedfellows remained hush-hush until 1977, when William Herland’s Investigative Report, disclosing long-suppressed information, was uncovered in Governor Thomas Dewey’s archives in 1954.  The report summarized testimony that detailed the Navy’s involvement in “Project Underworld.” [4]  Adding to the surprise was the breadth of the operation.

At the Casablanca Conference, convened on January 14, 1943, at the Anfa Hotel in Morocco, the Allies set their sights on Sicily following their victory in North Africa. [3]  Project Underworld, which began as an intelligence effort limited to the American home front, was radically altered when a secret US Joint Chiefs directive was issued on April 15, 1943, and explicitly recommended:

“Establishment of contact and communications with the leaders of separatist nuclei, disaffected workers, and clandestine radical groups, e.g., the Mafia, and giving them every possible aid.” [5]

This marked a formal US policy alignment with clandestine Sicilian actors, including Mafia figures, to undermine fascism and limit civil resistance in Sicily.  

The machinery of Project Underworld quickly pivoted toward this new strategic goal, the support of Operation Husky.  F-Target Section, a group dedicated to gathering data on the invasion zone in the Lascaris War Room complex, was formed.  Lucky loved the idea.  The Mafia could be especially useful to Allied planners faced with the daunting challenge of invading Europe through its Sicilian underbelly.  Though still imprisoned, Luciano’s narcotics smuggling network, which extended across the Atlantic and had close ties with the Sicilians, was harnessed. [3]  Soon, shadowy American Mafia figures were tasked with helping shape the Sicilian battlefield.  Once Sicily was rid of the Nazi occupiers, the Mafia would provide contacts to help establish an Allied Military Government.

The US Navy lacked the needed intelligence on Sicily.  Long considered an area primarily under British surveillance, the Navy lacked even the most 

A Local Sicilian Shows the Way

basic details on the island to support the initial amphibious landings, as well as further inland details: terrain topography, harbor details, resistance profiles, photographs, and street maps.  And of particular importance were contacts, those volunteers who could quietly guide troops once they landed, and lists of friendly Sicilian natives, underworld figures, and Mafia personalities who could be trusted and willing to join a guerrilla insurgent army.

Lucky volunteered to lead the Mafia resistance and offered his services, suggesting he was prepared “to be parachuted onto the island.”  The High Command vetoed that idea, reasoning that the release of an arch criminal could be a public relations nightmare. [3]  While the mafiosi were willing to fight, the speed of the competitive race between Patton and Montgomery to be the first to enter Messina, as well as the haste of the Nazi retreat, exceeded all expectations.  Fortunately, while partisans participated in some skirmishes, a guerrilla army was not needed.  Still, Luciano and his associates arranged for trusted Sicilian-American contacts to work with Naval Intelligence and the OSS.

As a result, hundreds of Sicilian-Italians were hauled into the Astoria headquarters.  “Little Man Lansky” later remarked that some of the Sicilians were very reluctant to cooperate with the Navy until Luciano’s name was dropped.  The interviewer would stop smiling and say, ‘Lucky will not be pleased to hear that you have not been helpful.’  Typical Mafia tactics, such as threats, were also effective.  At that point, information on Sicily began to pour in.  As the Sicilian D-Day drew closer, coastal photos and harbor sketches made their way into the hands of Allied cartographers on Malta.  An enormous, four-by-six-foot map of Sicily with a transparent plastic overlay detailing strategic points such as airfields, naval bases, and power plants was created from this flood of information. [3]  

From dockside mobsters to men in the Sicilian hills, messages were relayed.  Lists of pro-Allied civilians and known Fascist sympathizers were passed quietly from one trusted hand to another.  The Mafia’s assistance in the preparation of the invasion, from aiding in the mapping of Sicily to supplying pathfinders, effectively contributed to the success of Operation Husky.  On one side of the Atlantic, Luciano, incarcerated and the ‘Little Man,’ stood out.  In Sicily, another longtime capo was free to

Invasion of Sicily Landing Areas

operate.

A key contact at the Sicilian end of this network was Calogero Vizzini, also known as “Don Calò”.  He was one of the island’s most powerful and feared Mafia bosses, as opposed to his two brothers, who decided to be priests.  Legend has it that days before American troops landed at Gela and Licata, a scarf marked with an “L” for Luciano was airdropped near Don Calò’s farm as a tip-off of the invasion.  While the story of the scarf remains folklore, the results were real.  As American troops advanced inland from the beaches, they met little to no resistance in towns like Villalba and Mussomeli.  In some cases, local guides later claiming to be Mafiosi steered them through twisting roads and urged civilians not to resist.

 In collaboration with American Mafia boss "Lucky" Luciano, Vizzini and his men were supplied with artillery.  In one alleged instance, Don Calò himself rode into the town of San Martino in a Sherman tank.  The sight led Fascist soldiers to surrender.  He was just getting rolling. 

After the Mussolini regime and Nazis fled Sicily, the Allies needed local administrators to fill legislative spots in individual cities and towns. [2]  Intentionally or not, America traded Fascist brutality for Mafia influence as the Allied Military Government of Occupied Territories installed Mafiosi in administrative roles.  These decisions ultimately reshaped local power dynamics, fueling a postwar Mafia revival.  Seizing the opportunity as effortlessly as a chameleon changes its spots, Don Calò could flip his allegiance to whichever power benefited his interests.  With the Americans in ascendance, it would be as easy as changing a framed wall picture of Mussolini to one of Roosevelt or Eisenhower, if not both.  In Villalba, Don Calò was crowned mayor because of his staunch opposition to Fascist ideals, despite having aided Mussolini's rise to power years earlier.  He proved to be a cheery and popular mayor, greatly admired by the citizens, while maintaining a casual engagement in Mafia activities and displaying the notion that in war, yesterday’s enemy can be today’s ally.  

At war's end, the Navy burned all evidence of the Mafia’s cooperation. [3] What could Lucky expect from his collaboration?  What was in it for him?  A medal?  On May 8, 1945, the day of the Allied victory in Europe, V-E Day, Lucky requested executive clemency. [4]  Eight months later, on Jan. 3, 1946, Governor Thomas Dewey quietly commuted his sentence to the nearly ten years he’d already served “in recognition of his services to the Navy".  Instead of living out his days behind bars, Lucky was deported to Italy six days later, where he remained under surveillance.  Never quite free in light of his wartime cooperation, the US Department of Justice and Italian authorities continued to investigate his activities, particularly regarding suspected involvement in narcotics smuggling.  Government agents in the US and Italy followed him for years.  Still, despite their efforts, no narcotics case was successfully made against him.  Meanwhile, Don Calò, once hunted by Mussolini’s Blackshirts, now shook hands with Allied officers and became a symbol of the Mafia’s resurgence in post-Fascist Sicily. 

 In Messina, when General Patton and Field Marshall Montgomery shook hands, ending the 39-day Sicilian campaign, it’s doubtful they knew just how much help had come from Mafia men like Luciano and Don Calò.  The scope of their role in the Allied success in Sicily remains one of the more curious and often debated footnotes of wartime espionage history.  Historians debate the Mafia’s impact.  Some argue that it has been mythologized, claiming that the postwar press, retelling, and Hollywood mythmaking have inflated its influence.  Others insist it was decisive, and that, without question, Luciano helped protect American ports and secured the cooperation of Sicilian Mafiosi during the war.  What remains a fact is that the American Mafia supported the Allied invasion of Sicily, and dockside at home.  Even limited cooperation, if it saved lives or
eased the occupation of Sicily, justified the deal.

Back in my Connecticut childhood, the men in white hats were clean-shaven, quick to help the needy, and always on the side of justice.  In 1943, on

The Lone Ranger's White Hat

the docks of New York and the hills of Sicily, the “good guys,” men with names like Lucky, Lansky, and Don Calò, were cloaked in secrecy and stained by violence.  Whatever their motivation: patriotism, justice, continued survival, or greater control at war's end, the fact remains that in a war painted in stark shades of good and evil, even the Mafia had a part.  For a brief, strange moment, they had taken the role of ‘Good Guys,’ and though never spotless, they wore white hats.  Yet, the Mafia’s stead as “Good Guys” was temporary, only lasting as long as the war required.  When the shooting stopped, moral ambiguity disappeared in the shadow cast by white hats and saw their hats quickly dirty and fade back to black. 


From That Rogue Tourist,

Paolo


[1]  Project Underworld, https://warfarehistorynetwork.com/article/project-underworld-the-u-s-navys-secret-pact-with-the-mafia/

[2]  How the Mafia Works, https://people.howstuffworks.com/mafia.htm

[3]  Project Underworld Enlisted the Help of Organized Crime to Fight the Axis, Article by Gregory Peduto, November 2009 Archives, Warfare History Network, https://warfarehistorynetwork.com/issue/wwii-history-november-2009-issue/

[4]  Secret Report Sites Luciano on War Aid, New York Times, https://www.nytimes.com/1977/10/09/archives/secret-report-cites-luciano-on-war-aid-book-based-on-a-54-study.html

[5]  Collaborations between the United States government and Italian Mafia ,https://en.wikipedia.org/wiki/Collaborations_between_the_United_States_government_and_Italian_Mafia

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