Denver’s Mafia Secrets: The Smaldones’ Control of North Denver at Their HQ Gaetano’s

Denver’s quiet neighborhoods hide one of America’s most fascinating mob stories. Long before breweries and coffee shops filled the streets of North Denver, this area was controlled by the Smaldone crime family. Their story begins in Denver’s Little Italy, where Italian immigrants built a tight-knit community that later became ground zero for bootlegging, gambling, and organized crime in Colorado. In this video, we uncover how three brothers — Clyde, Eugene “Checkers,” and Clarence “Chauncey” Smaldone — rose from stealing bootleg liquor as teenagers to becoming the undisputed kings of Denver’s underworld for nearly half a century.

The Smaldones’ empire started during Prohibition. As teenagers, Clyde and Checkers discovered hidden bootlegger stashes and began selling the stolen liquor to speakeasies. Soon, they were making their own booze, trucking whiskey from Canada, and forging ties with Al Capone’s Chicago outfit. Colorado was no stranger to mob violence at the time — rival gangs from Pueblo and Trinidad fought bloody turf wars, and gangland murders were a regular occurrence. When their employer, Denver mob boss Joe Roma, was murdered in 1933, the Smaldones stepped into the power vacuum and built their own criminal dynasty.

As Prohibition ended, the brothers pivoted to gambling. They opened underground casinos, controlled hundreds of slot machines across Denver, and took sports bets that brought in thousands each week. Their reach extended into Central City, where they ran the Monte Carlo casino and curried favor with city officials by funding waterlines, restoring homes, and supporting school lunch programs. Their blend of charm, intimidation, and influence allowed them to operate for decades, often under the nose of law enforcement.

At the center of their operations was Gaetano’s, the Italian restaurant the Smaldones opened on Tejon Street in 1947. Gaetano’s quickly became their headquarters and social hub. Clyde could always be found at the barstool furthest from the door, impeccably dressed and smoking a cigar. Checkers, the family’s enforcer, mixed a tough-guy persona with moments of unexpected warmth, sometimes breaking into opera songs after a few drinks. Chauncey preferred the back table — known as Table 404 — where he famously ate what later became the “Chauncey Burger,” topped with mozzarella and roasted Italian peppers.

Gaetano’s wasn’t just a mob hangout; it was also beloved in the community. Locals remember the Smaldones for quietly paying tuition for neighborhood kids, donating to Catholic orphanages, and ensuring no family went hungry. This duality defined their legacy — part ruthless criminals, part community benefactors. Depending on who you ask, they were either feared gangsters or Robin Hood figures. In the 1950s and 1960s, they were at the height of their power, but repeated prosecutions and prison sentences chipped away at their control. By the 1980s, the era of the Smaldones had ended, but their story still echoes in Denver’s history.

Today, Gaetano’s stands as a monument to that past. The restaurant has changed hands, but it maintains its old charm with wood paneling, mob photos, and a menu that honors its roots. When we visited for this video, I ordered the eggplant parmesan and Kenny went for the sausage sandwich — both were excellent and served in the same booths where deals were once made. Sitting in Clyde’s spot at the bar, it’s hard not to imagine the whispers and plans that once filled the air.

This video blends our visit to Gaetano’s with archival history from Colorado Life Magazine and other sources to tell the full story of the Smaldones — from their early days in Little Italy to their rise as Denver’s most notorious crime family, their complicated relationship with the community, and their eventual decline. It’s a piece of Denver history that lives on in the city’s memory and in the walls of one unassuming Italian restaurant.

Explore Gaetano’s:
https://www.gaetanositalian.com

Read the Colorado Life Magazine article we used for this video:
https://www.coloradolifemagazine.com/...

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https://symbiohomes.com/north-side

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00:00 Intro
02:16 Symbio
03:13 Gaetano's Restaurant
04:15 Headquarters
06:53 Prohibition in Denver
09:21 Rise to Power
11:37 Total Control of North Denver
14:28 Gambling
17:30 End of an Era
21:54 Mob Homes