Smaldone, Denver's Mob Family

Brothers Clyde and Checkers Smaldone used their north Denver family restaurant, Gaetano’s, as the headquarters from which they built a mob empire. The Smaldone underworld enterprise died out, but Gaetano’s remains.

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CLYDE AND CHECKERS, born in 1906 and 1910, respectively, were the oldest sons of the nine children of Raffaele and Mamie Smaldone, immigrants from Potenza, Italy. It was in Denver’s north-side Italian enclave during Prohibition that they started building their empire. As teenagers, they would find where the bootleggers stashed their illicit booze. Then they stole it and sold it to speakeasies.

They graduated into making their own liquor, then started trucking in premium whiskey from Canada, and finally, buying it from Al Capone’s Chicago outfit.

Colorado’s rival gangs fought for control of bootlegging, and during prohibition there were some 30 gangland murders. In the south, the Dannas out of Trinidad and the Carlinos from Pueblo fought for supremacy.

In Denver, the Smaldones' employer was Joe Roma, the 5-foot-1 mob boss kingpin known as “Little Caesar.” And like his namesake, Roma met a bloody end when in 1933 he was shot seven times – six in the head – in his North Denver home. The killers were never prosecuted, and the Smaldones always denied involvement, but Roma’s death meant that the Smaldones were undisputed kings of the Italian mob in Denver.

Clyde and Checkers spent the last days of Prohibition in Leavenworth Federal Penitentiary, returning to Denver in 1934 after 18 month stints to find their bootlegging business obsolete. They moved seamlessly to gambling, where they worked with Ova Elijah “Smiling Charlie” Stephens, who ran a high-end restaurant that doubled as a casino. Stephens, Clyde and Checkers were convicted in the car-bombing of Stephens’ erstwhile casino partner and were sent to state prison at Cañon City.

After the Smaldones were freed in the early 1940s, they found their greatest success through their mother’s cooking. In 1947, the brothers founded Gaetano’s, which thrived.

That same year they opened a casino, dubbed Monte Carlo, in the old mining town of Central City. Respectable people from Denver and across the state flocked to play craps, roulette and slot machines. Clyde’s charm persuaded city officials to look the other way, and as a token of thanks, the Smaldones paid for new waterlines for Central City, restored dilapidated houses and funded a school lunch program.

“If you know how to talk to people you can make money anywhere and you don’t have to say, ‘It’s a bribe,’” Clyde said years later.

The Smaldones’ casino in Central City was illegal at the time, but Clyde predicted such gambling would be legalized if the government knew how much money there was to be made. But it took more than 40 years before the state approved gambling in Central City and other mountain towns, where many casinos now do booming – and legal – multimillion dollar business.

The Smaldone gambling racket spread across Colorado in the late 1940s and included at one time more than 500 slot machines. They also did a lot of business taking bets on sporting events.

The Smaldones’ success rankled prosecutors, who made an allout push to get them. Checkers was charged with tax evasion and was to stand trial. When the Smaldones sought out potential jurors to coax a “not guilty” verdict, they were accused of jury tampering. They were tried and convicted, but the judge’s ruling was thrown out. Instead of going through a second trial with a new judge, Clyde and Checkers worked out a plea bargain in which they would each serve three concurrent four-year terms. But the judge changed the agreement to three consecutive terms, and the brothers were sentenced in 1953 to 12-years in Leavenworth.

The family business continued with the youngest Smaldone brother Chauncey, taking control, along with nephew Paul “Fat Paulie” Villano. Clyde retired from his role when he got out in 1963, but Checkers stayed involved. In the 1970s, the family struggled with independent bookmakers who no longer recognized the Smaldone control of gambling in Denver. One such upstart, former University of Colorado football player Skip LaGuardia, was killed by a shotgun blast to the face outside his Denver home. The Smaldones were widely thought to be behind it, but no charges were made.

The Smaldones’ power continued to fade as the main players grew old and no one was recruited to take their place. By the time Checkers was sentenced to another prison term in the 1980s for loansharking, the Smaldones had effectively ceased to exist as a criminal enterprise in Denver.


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