Introduction
You want to understand the hidden history of American syndicates beyond the famous East Coast families. Dick Kreck documents the rise, reign, and decline of the Smaldone family in Denver and Colorado.
The Smaldone brothers rose from immigrant poverty to build a four-decade criminal syndicate controlling gambling and bootlegging in Colorado.
The book covers early immigrant struggles, Prohibition bootlegging, gang wars, political corruption, and the eventual fall of the enterprise. You will discover how regional criminal networks operated in the American West.
Consider these questions as you read:
- How did immigrant poverty shape organized crime in Denver?
- What role did political corruption play in the survival of the syndicate?
- How did the Smaldones transition from bootlegging to legalized ventures?
1. Immigrant Roots and Early Bootlegging
The Smaldone family escaped poverty through hard work and illicit liquor operations during Prohibition.
Arrivals and Hardship
Raffaele Smaldone immigrated from Potenza, Italy, arriving in New York before moving to Colorado in 1889. He worked initially for the railroad for 30 dollars a month and later became a fruit and vegetable peddler. His earnings on the railroad eventually increased to 40 dollars a month as a foreman. This raise allowed him to install an indoor toilet and bathtub and get rid of the backyard outhouse.
Early Italian immigrants in Colorado faced severe economic exploitation, cultural prejudice, and violent backlash from nativists. Immigrants labored in dangerous trades for daily earnings of 1.25 to 1.75 dollars under exploitative labor contractors known as padrones, compared to a standard union miner wage of 3 dollars a day. An immigrant often carried an average cash amount of only 11 dollars upon arrival. By 1930, the Italian-born population in Denver reached 10,670 citizens.
Hostility frequently manifested in riots, beatings, and extrajudicial lynchings fueled by anti-immigrant sentiment. In 1893, an angry mob of 10,000 people stormed the Arapahoe County jail, dragged out a 28-year-old Italian named Daniel Arata, hanged him from a cottonwood tree, and mutilated his body.
Despite these hardships, the Smaldone family instilled a strict work ethic and deep domestic dependability in their children. Raffaele and Mamie Smaldone had 11 children in total, with 9 reaching maturity, including 6 boys who shared the front bedroom on Osage Street. Clyde and his brothers began working as young children, performing menial chores and peddling produce with their father.
As a young boy, Clyde walked all the way across the Twentieth Street Bridge by himself to sell newspapers at Sixteenth and California, bringing his earnings home to his mother.
Prohibition and Capone Connections
During Prohibition, the Smaldone brothers began their criminal careers by stealing and peddling illicit liquor before building a large-scale interstate bootlegging operation. Clyde Smaldone and Gerald Nevins started as teenagers by stealing whiskey from local bootleggers and reselling it cheaply. Clyde later partnered with his brother Checkers, operating from an office on Thirty-fourth and Pecos, sourcing bonded whiskey from Canada and high-grade alcohol from Iowa.
Clyde drove modified Fords equipped with overload springs and three spotlights on the windshield to haul illegal liquor loads from Canada and Mexico. A typical haul of bonded liquor from Canada consisted of 42 cases.
Clyde established direct connections with the Chicago mob during the 1920s to secure cheaper, high-quality bonded liquor. He traveled to Chicago to meet with associates of Al Capone to arrange a more efficient supply chain and lower wholesale costs for importing liquor across the Mississippi River. Clyde's original cost before meeting Capone's associates was 66 dollars a case.
Al Capone personally intervened to lower Clyde's acquisition cost to 35 dollars a case with a minimal transportation fee.
Clyde and Checkers took prison sentences to protect their aging parents from federal prosecution for operating a family still. When federal authorities caught Raffaele and Mamie selling liquor out of their home, the brothers pleaded guilty to federal liquor violations in exchange for the release of their parents. Federal Judge J. Foster Symes sentenced Clyde and Checkers to 18 months at Leavenworth, expressing regret that the owners of a still had not killed them off during a previous gunfight. Each brother received a financial penalty of 1,000 dollars.
2. The Rise of the Syndicate
Following the assassination of Joe Roma in 1933, the Smaldone brothers seized control of Colorado rackets amid widespread political corruption.
The Death of Joe Roma
Joe Roma, known as Little Caesar because of his small stature, was murdered in his North Denver home by unknown gunmen who riddled him with seven bullets at close range. Clyde and Checkers Smaldone were questioned along with associates because they had visited Roma hours before his death. They were never charged, ultimately benefiting most from his demise at 37 years old.
Joe Roma's lavish funeral featured a three-thousand-dollar polished copper casket and a six-foot-tall Golden Gateway floral display, drawing a crowd of two thousand onlookers. The 3504 Vallejo Street home address became the backdrop for a sudden shift in local power.
Politics and the KKK
Prohibition failed to create a sober society, instead sparking widespread lawlessness, widespread illegal alcohol production, and a booming black market. The Eighteenth Amendment banned the manufacture, sale, and transportation of alcohol, leading to widespread defiance by otherwise law-abiding citizens and a massive illicit liquor trade run by mobsters who profited immensely tax-free.
By the mid-1920s, Al Capone was reaping an estimated $60 million a year, and a half-million Americans were involved in the illicit booze business after the Eighteenth Amendment was approved nationally when Wyoming became the thirty-sixth state to ratify on January 16, 1919. Colorado went dry ahead of the national movement, shutting down thousands of saloons and breweries while introducing numerous legal loopholes. Coloradans voted to go dry in 1914, shutting down all 467 licensed saloons, 550 illicit grog shops, and a total of 1,500 saloons across Colorado by the end of 1915.
The Denver Athletic Club disposed of its wine cellar by selling discounted bottles to members, including all twelve of the only known bottles of 1884 Schloss Johannisberg cognac. Shortly after the law went into effect, 16,000 prescription forms for doctors were issued, and Denver city auditor Fred Stackhouse issued 59,339 liquor permits to individuals in 1917.
Because quality bonded liquor was scarce and expensive, average citizens brewed their own concoctions. Poor distillation or the addition of toxic ingredients like embalming fluid, rubbing alcohol, or paint thinner frequently caused blindness, organ failure, and death. Locally produced moonshine was known as Sugar Moon or Leadville Moon, the latter rumored to be made using black powder and old miners' overalls, sold across 324,000 square miles of territory covered by very few enforcement agents at prices ranging from 35 cents to $3.
Public dissatisfaction with Prohibition and its economic costs eventually led to its repeal, transforming drinking establishments into modern taverns. At 12:01 am on Friday, April 7, 1933, the first cases of 3.2 beer rolled out of the Coors brewery in Golden, Colorado, ending thirteen years of drought under the Twenty-first Amendment.
During the 1920s, the Ku Klux Klan gained immense political power in Colorado, coexisting with and often overlooking the rampant bootlegging industry. The Klan arrived in Denver in 1921, hitting the height of its power in Colorado politics from 1923 to 1926 while mayor Benjamin Stapleton served six terms starting in 1923. Bootleggers like Clyde Smaldone found that the Klan-backed administration and police force largely ignored their illegal operations as long as they kept a low profile and maintained order.
Clyde Smaldone used his connections with Governor Clarence Morley, a KKK member, to resolve a beat-patrol issue for African American police officers working near his father's speakeasy. The immense profits of bootlegging triggered a bloody wave of gang warfare and assassinations across Colorado between 1919 and 1933. Thirty or more gang murders took place in Colorado between 1919 and 1933, including 21 shots fired into patrolman Richie Rose during his assassination in October 1922.
Brothers Tony and Pete Danna were shredded by thirty to fourty pieces of buckshot from sawed-off shotguns fired by rival Carlino faction members from a passing Hudson automobile in Pueblo in May 1926. Following the murder of local mob boss Joe Roma in 1933, brothers Clyde and Checkers Smaldone took control of Denver's underworld at ages twenty-seven and twenty-three respectively, organizing local gangs into an efficient syndicate that controlled illegal liquor, gambling, bookmaking, and loan-sharking for the next four decades.
3. Gambling Enterprises and Underworld Violence
The syndicate expanded into high-stakes gambling and loan-sharking while managing internal conflicts and intense prison sentences.
Casinos and Car Bombings
The Smaldone brothers partnered with Ova Elijah Smiling Charlie Stephens to run the Blakeland Inn. This venue operated as a major hub for gambling and entertainment starting in 1933. Stephens ran a series of clubs featuring roulette, craps, and slot machines alongside upscale dining. The operation ended due to pressure from clergymen and a violent falling out among partners.
Adeline Tate Morris, a high school student who danced in the stage shows in 1935 and 1936, recalled that Stephens treated the performers like an uncle while society patrons lost money at the tables. Chorus dancers received a weekly pay of $10 for three shows a night, seven days a week. The Blakeland Inn officially closed in 1936.
A dispute over control of gambling operations at the Blakeland Inn led to an attempted assassination via a car bomb. When gambler Leo Barnes attempted to seize more control from Charlie Stephens, a black-powder bomb was planted under Barnes's car. This resulted in serious injuries to Barnes and subsequent prison sentences for the Smaldones and Stephens.
On December 8, 1936, Leo Barnes and his wife Pernee entered their Ford sedan in downtown Denver. When Barnes turned the ignition, an explosion blew Barnes through the roof and destroyed the vehicle. Clyde, Checkers, and Stephens received prison sentences of 7 to 10 years for conspiracy and assault to commit murder.
Prison and Enforcement
Clyde Smaldone engaged in ongoing conflicts with brutal prison warden Roy Best while serving time at the Colorado state penitentiary. Roy Best served a 20-year tenure as head of Cañon City. Clyde refused to show deference to the beloved Best, leading to severe punishments including forced labor on the hill gang chained to a wheelbarrow. His brother Checkers, by contrast, became a compliant trusty.
When Clyde arrived at Cañon City and greeted the warden by his first name, Best denied him trusty status and assigned him to harsh physical labor where guards used whips.
Checkers Smaldone earned a reputation for coolness under pressure by intervening during a prison break at Leavenworth. When an armed inmate invaded the warden's home and took his young niece and nephew hostage, Checkers disarmed the situation by ignoring the threat to himself and safely securing the children in an upstairs bedroom. The escape plan had involved $500 for a get-away car.
Red Fenwick documented how Checkers looked at the gunman's weapon, told him not to interfere with his business, led the children to a bedroom, and played checkers with them for over an hour.
The Smaldone brothers cultivated a public reputation as generous benefactors to the poor while simultaneously running criminal enterprises. Despite their involvement in rackets, the Smaldones frequently provided groceries, coal, and milk to destitute North Denver families, funded college tuition for local boys, and supported Catholic orphanages. Clyde and his associates even collected $50,000 in cash to build a Catholic high school.
During Christmas, Clyde would bring a crippled orphan in a wheelchair to his family's holiday dinner and ensure he received a lap full of wrapped gifts.
Checkers Smaldone and his associates engaged in a violent daylight shootout to collect unpaid gambling debts. An argument over money owed by a bookmaker escalated into a violent clash involving Mace and firearms inside a North Denver ice cream parlor.
On April 13, 1970, a meeting at Darlene's Ice Cream Parlor between Checkers, Joe Salardino, and debtor Joe Nuoci erupted into gunfire. Nuoci sprayed the men with Mace, and a gun battle ensued when Checkers, who was fifty-nine years old at the time, reacted.
Checkers Smaldone maintained a strict detestation of the drug trade. Yet, Checkers and his wife Frances spoiled their only son, Young Eugene, shielding him from consequences until his drug abuse and spendthrift habits forced a final estrangement. Despite his underworld toughness, Checkers finally broke ties with his son, telling him he wanted no part of a dopehead.
4. Gaetano's and the Peak Empire
During the late 1940s and early 1950s, the Smaldones reached their economic peak through slot machines, political alliances, and Gaetano's restaurant.
Regional Expansion
The Denver-based syndicate worked cooperatively with southern bosses like Charley Blanda, Gus Salardino, Jim Colletti, and Scotty Spinuzzi. You can see how the Smaldone syndicate formed a strategic alliance with Pueblo mafia bosses to divide Colorado into northern and southern gambling empires. Clyde Smaldone supplied Pueblo boss Charley Blanda with slot machines for his Holiday Inn and other bars, ensuring local officials were decorated with payoffs.
During the peak years when the Colorado Fuel & Iron Company mills employed 6,000 men in Pueblo from 1914 to 1929, criminal profits flowed steadily. The 25th wedding anniversary celebration for Charley and Cora Blanda cost $3,500 in 1948 and featured 750 silver dollars given as a gift. Charley Blanda and Tom Incerto were later indicted in 1952 for failing to pay $10,692 and $29,398 in income taxes respectively.
Clyde Smaldone cultivated close personal relationships with high-ranking political figures, judges, and rival national mob bosses. Smaldone smuggled whiskey onto Franklin D. Roosevelt's campaign train during the 8,900-mile campaign tour stop in Denver on September 15, 1932. He also met with Herbert Hoover and maintained lifelong ties with Colorado Governor Ralph Carr, who pardoned Clyde Smaldone from Cañon City prison in 1942.
Wartime Black Markets and Gaetano's
During World War II rationing from 1942 to 1945, the Smaldones leveraged a federal rationing official to run a massive black-market operation supplying scarce commodities and gasoline stamps. Frank Curley, a federal rationing administrator, supplied Clyde with unrestricted gasoline stamps and ration items in exchange for favors and goodwill. Mildred Smaldone drove her car to Los Angeles multiple times with her son Gene to deliver black-market gas coupons to a station owner named Pizzichino, frequented by actors like Ronald Reagan and Frank Sinatra.
The early 1950s marked the economic peak of the Smaldone criminal enterprise, driven by slot machines, football parlay cards, loan-sharking, and Gaetano's restaurant. Operating from their legal base at Gaetano's restaurant—purchased with borrowed funds and paid off using football parlay cards—the Smaldones managed hundreds of slot machines, nightly barbooth games with high interest loan rates, and sports bookmaking. The high-water mark years for the Smaldone empire ran from 1946 to 1953, generating up to $1 million a year.
The Smaldones owned 585 slot machines across Colorado before selling them to Las Vegas interests including Bugsy Siegel. Clyde borrowed $22,000 from Jerry Losasso in 1947 to buy the property for Gaetano's restaurant.
Clyde's young son Chuck once grabbed a handful of cash containing two or three thousand dollars from a table pile to pay the Happy Home Bakery man for powdered-sugar donuts.
To participate in the nightly barbooth games run by the syndicate, you follow specific rules:
- Toss a pair of dice as the shooter while the come-out man puts up a stake.
- Roll one of the four winning numbers (3-3, 5-5, 6-6, 6-5) or avoid the four losing numbers (1-1, 2-2, 4-4, 1-2).
- Pay a periodic small amount called the pinch to the organizers to stay in the dice game.
Conclusion
The history of the Smaldone empire demonstrates how criminal syndicates rise through opportunistic violence and political corruption before eventually collapsing under federal pressure. You can trace the arc from immigrant poverty to peak influence and inevitable destruction. Dick Kreck shows that organized crime leaves behind a trail of ruined lives, prison terms, and fractured families.
To understand the full reality of historical underworld figures, you must evaluate several practical principles:
- Examine primary sources and oral histories to separate romanticized myth from documented criminality.
- Recognize that political corruption and protection enable long-running illicit enterprises to flourish.
- Observe how federal investigations and modern surveillance techniques dismantle entrenched syndicates over time.
- Remember that criminal empires ultimately yield severe personal loss and institutional decay rather than lasting security.
10 Key Ideas
- The Smaldone brothers rose from immigrant poverty to build a four-decade criminal syndicate controlling gambling and bootlegging in Colorado.
- The Smaldone family escaped poverty through hard work and illicit liquor operations during Prohibition.
- Al Capone personally intervened to lower Clyde's acquisition cost to 35 dollars a case with a minimal transportation fee.
- Following the assassination of Joe Roma in 1933, the Smaldone brothers seized control of Colorado rackets amid widespread political corruption.
- Brothers Clyde and Checkers Smaldone took control of Denver's underworld at ages twenty-seven and twenty-three respectively, organizing local gangs into an efficient syndicate that controlled illegal liquor, gambling, bookmaking, and loan-sharking for the next four decades.
- The syndicate expanded into high-stakes gambling and loan-sharking while managing internal conflicts and intense prison sentences.
- Despite their involvement in rackets, the Smaldones frequently provided groceries, coal, and milk to destitute North Denver families, funded college tuition for local boys, and supported Catholic orphanages.
- During the late 1940s and early 1950s, the Smaldones reached their economic peak through slot machines, political alliances, and Gaetano's restaurant.
- The high-water mark years for the Smaldone empire ran from 1946 to 1953, generating up to $1 million a year.
- The history of the Smaldone empire demonstrates how criminal syndicates rise through opportunistic violence and political corruption before eventually collapsing under federal pressure.