Fact-checked by Grok 2 weeks ago

Big Jim Colosimo

Vincenzo Giacomo "Big Jim" Colosimo (c. 1878 – May 11, 1920) was an Italian-American figure who immigrated from , , and established a dominant vice syndicate in Chicago's Levee District, controlling , , and rackets from around 1902 until his assassination. Starting as a and early , Colosimo consolidated disparate Italian criminal elements into a structured operation, earning nicknames like "Diamond Jim" for his flamboyant style and lavish spending on jewelry and his cafe-restaurant. His empire focused primarily on tolerated vice rather than bootlegging, despite the impending era, which reportedly led to tensions with associates like who sought expansion into alcohol smuggling. On May 11, 1920, Colosimo was shot dead in the lobby of his own restaurant at 2126 South Wabash Avenue by an unidentified gunman, widely believed to be arranged by Torrio with execution by to seize control and pivot the organization toward Prohibition-era profits. Colosimo's death marked the transition of his gang into the more expansive under Torrio and later , transforming it into one of America's most powerful families through bootlegging dominance. No one was ever convicted for the murder, reflecting the era's challenges in prosecuting mob hits amid corrupt policing and witness intimidation.

Early Life and Immigration

Childhood in Italy and Arrival in America

Vincenzo Colosimo, later known as Big Jim, was born on February 16, 1878, in the small mountain village of Colosimi in , . Historical records provide scant details on his childhood, which unfolded in a rural, impoverished region of characterized by agricultural labor and limited opportunities, though no specific family or personal events from this period are documented in primary sources. In 1895, at the age of 17, Colosimo immigrated to the with his family, settling in Chicago's neighborhood amid a wave of migration driven by economic hardship and unification-era disruptions in . The journey reflected broader patterns of late-19th-century emigration, with over 4 million Italians arriving in America between 1880 and 1920, many from seeking industrial work in urban centers like . Upon arrival, Colosimo entered a burgeoning Italian-American community in the city's Near South Side, where ethnic enclaves provided initial social networks but also fertile ground for informal economies.

Initial Jobs and Political Entry in Chicago

Upon arriving in Chicago in 1895 at age 17, Vincenzo Colosimo, known as Big Jim, began working as a , a city job arranged by First Ward Michael "Hinky Dink" Kenna, who took a liking to the young immigrant. Colosimo advanced to the role of foreman among fellow immigrant laborers, leveraging his position to organize and influence the community. Concurrently, Colosimo supplemented his legitimate employment with petty criminal activities, including , thievery, and early involvement in by engaging women to work for him as a teenager. These ventures drew the attention of First Ward political bosses and John "Bathhouse" Coughlin, who recognized his utility in mobilizing voters and collecting graft. Kenna and Coughlin elevated Colosimo to in their machine organization, a role that entailed securing votes, managing local patronage, and enforcing political loyalty in Chicago's Levee District vice hub. He later served as their , responsible for gathering protection money from brothels, saloons, and operations under the ward's tolerated vice economy. This political integration provided Colosimo with essential cover and influence, enabling his transition from menial labor and small-time crime to leadership in organized vice.

Rise in the Vice Trade

Establishment of Prostitution Networks

Colosimo began establishing his influence in Chicago's vice trade in the late 1890s by providing protection rackets to street prostitutes and independent madams operating in the , a segregated red-light area south of the known for its dense concentration of illicit activities. This initial role as an allowed him to collect fees for safeguarding workers from rival gangs, theft, and police interference, leveraging his physical stature—standing over six feet tall and weighing more than 250 pounds—and connections within immigrant communities. By organizing disparate street-level operations under a centralized authority, Colosimo transitioned from petty to systematic control, reducing inter-gang violence through and payoffs to local politicians. In 1902, Colosimo solidified his foothold by marrying Victoria Moresco, a widow and experienced who already managed established brothels in the , including operations that catered to a mix of working-class and affluent clients. The marriage granted him direct ownership stakes in her properties, such as the Victoria brothel—named in her honor—and the , which served as flagship establishments featuring luxurious interiors to attract higher-paying customers. Moresco's pre-existing network provided Colosimo with operational knowledge, supplier contacts for furnishings and staffing, and routes for recruiting women from immigrant pools, enabling rapid scaling from a handful of houses to a broader . Under Colosimo's leadership, the network expanded aggressively throughout the and , incorporating tactics like coercing independent operators into tribute payments or outright acquisition of their venues, resulting in control over approximately 200 brothels by the late across the and extending into Chicago's suburbs. He maintained dominance by deploying a cadre of enforcers to enforce exclusivity, suppress from or non-Italian gangs, and ensure steady through fixed pricing and volume—estimated to generate hundreds of thousands of dollars annually before reforms targeted vice districts. This structure prefigured modern hierarchies, with Colosimo acting as the primary beneficiary while subordinates handled daily collections and dispute resolution, though his reluctance to diversify beyond limited into related supply chains like routes.

Expansion into Gambling and Saloons

Following his consolidation of prostitution rackets, Colosimo diversified into houses and saloons during the early 1900s, leveraging the District's economy to build a multifaceted criminal network. These ventures, centered on Chicago's South Side, included operations at addresses like 2222 South Wabash Avenue, where a house was managed under his oversight. By integrating —such as wheels and games—with saloon-based sales, Colosimo generated substantial profits that funded further expansion and of local officials. A pivotal establishment in this phase was Colosimo's , opened around 1909–1910 on Archer Avenue as a venue for and consumption targeted at male patrons. In December 1913, it relocated to 2126–2128 South Wabash Avenue (within the ), where it was remodeled into a more upscale cafe with entertainment features like and an , functioning as both a legitimate front and operational hub. This site attracted politicians and judges, facilitating rackets, while saloon affiliates extended Colosimo's influence over distribution. to , he invested $25,000 in a owned by saloon operator Jake "Greasy Thumb" Guzik, ensuring supply chains for his drinking establishments. These expansions solidified Colosimo's control over interconnected vice sectors, with and complementing by drawing crowds and enabling cross-promotion of illicit activities. Profits from these sources, estimated to rival his revenues, were reinvested into political , though exact figures remain undocumented due to the era's cash-based operations. By centralizing disparate and outfits under his command, Colosimo transformed fragmented street-level rackets into a proto-syndicate structure.

Organizational Growth and Alliances

Political Patronage and Corruption Ties

Colosimo forged key alliances with Chicago's First Ward Democratic machine, serving as a for aldermen John "Bathhouse John" Coughlin and Michael "Hinky Dink" Kenna, who dominated the Levee District's vice economy through systematic graft. These politicians, notorious for extracting protection money from brothels, dens, and saloons, appointed Colosimo to a low-level municipal role as a street sweeper around 1900, providing him cover to expand his rackets without interference. Acting as a "," Colosimo collected and disbursed bribes from vice operators to captains and ward officials, ensuring raids were avoided and operations thrived in the segregated . His political insider status allowed him to influence vice commission investigations, such as the 1911 Chicago Vice Commission report, which documented but failed to dismantle corruption due to entrenched payoffs totaling thousands of dollars monthly across the district. By 1910, Colosimo controlled over 20 percent of the city's brothels, sustained by these ties that neutralized reform efforts from figures like Mayor Fred Busse. These relationships exemplified Chicago's symbiotic underworld-political nexus, where Colosimo's loyalty bought judicial leniency—evidenced by his avoidance of serious prosecution despite operating openly—and reciprocal favors, including mobilization during elections. Critics, including contemporary reformers, highlighted how such eroded , with police budgets indirectly funded by vice graft funneled through aldermen like Coughlin and , who amassed personal fortunes estimated in the hundreds of thousands by the . Colosimo's model persisted, influencing successors in the Chicago Outfit's strategies.

Recruitment of New York Associates

In 1909, amid escalating threats from extortionists targeting his Chicago vice operations, Colosimo recruited Giovanni "Johnny" Torrio from to serve as an and manager. Torrio, the nephew of Colosimo's second wife Victoria Moresco, had established a reputation in Brooklyn's underworld by operating a that fronted a prosperous ring, providing him with direct experience in the Levee-style rackets Colosimo dominated in . This familial connection facilitated Torrio's relocation, where he assumed a role, importing organizational methods from New York's to streamline Colosimo's brothels and saloons against rival incursions. Torrio's arrival bolstered Colosimo's defenses, enabling aggressive expansion of the networks by quelling internal disputes and external pressures through calculated and alliances. Under Torrio's influence, Colosimo's syndicate adopted more structured hierarchies, drawing on 's proto-Mafia tactics to integrate dens and protect lucrative territories, though Colosimo himself maintained operational until Torrio's growing foreshadowed shifts in power. This recruitment not only neutralized immediate activities but also laid groundwork for cross-city collaborations, as Torrio later leveraged contacts to recruit additional talent, including in late 1919, further professionalizing the enterprise.

Personal Affairs and Lifestyle

Marriages and Romantic Entanglements

Colosimo's first marriage was to Victoria Moresco, an established who operated brothels in Chicago's district, with the union occurring in 1902. This partnership merged Moresco's existing operations with Colosimo's political influence and enforcement capabilities, enabling rapid expansion of their vice network; Moresco, aunt to future associate , actively co-managed these enterprises alongside her husband. The couple divorced in early 1920, amid Colosimo's growing infatuation with a younger performer. In April 1920, weeks before his death, Colosimo married Dale Winter, a 29-year-old singer and dancer he had encountered at one of his establishments; the ceremony took place on April 17 at the in . Winter, previously performing in Ziegfeld Follies-style revues, represented a shift toward Colosimo's personal indulgences, with contemporaries noting his preoccupation with the relationship as a distraction from business pressures like enforcement. The marriage lasted less than a month, ending with Colosimo's on May 11, 1920; Winter later remarried and pursued entertainment ventures. Colosimo's broader romantic pursuits aligned with his vice empire, as his affinity for women reportedly drove investments in rings, though no other long-term entanglements beyond these marriages are well-documented in primary accounts.

Lavish Expenditures and Public Persona

Colosimo cultivated a flamboyant public persona as "Diamond Jim," characterized by ostentatious displays of wealth derived from his vice operations, which reportedly generated $50,000 monthly by the late . He favored flashy attire, including white suits or garish checkered patterns accented with extensive jewelry—such as rings on every finger, shirt studs, a horseshoe vest pin, , belt buckles, and suspender buckles—earning his for this gem obsession. His inventory after death revealed items like -studded garters valued at $60 and suspenders with buckles at $200, reflecting a personal collection he reportedly handled leisurely from buckskin bags. His expenditures extended to luxurious properties and vehicles, including a palatial at 3156 S. Vernon furnished with servants, and statuary, deep rugs, and rare coin collections, alongside two chauffeured limousines. Colosimo's flagship venue, Colosimo’s Café on South Wabash , featured opulent interiors with gilded doorknobs, green velvet walls, and a frescoed , serving as both a dining spot for politicians, judges, and celebrities and a hub for his criminal dealings. He invested $25,000 in a operated by associate "Greasy Thumb" Guzik prior to , showcasing strategic yet lavish financial moves. In social habits, Colosimo projected generosity and extravagance, routinely distributing $1,000 bills to favored gamblers at his establishments and hosting lavish dinners with complimentary champagne and cigars for patrons. He funded voice lessons for his second wife, singer Dale Winter, aiming to elevate her to operatic status, and maintained a high-profile presence in Chicago's fashionable district. This public image of opulence, bolstered by bribes to officials, contrasted with underlying vulnerabilities, culminating in his 1920 funeral's $7,500 silver-and-mahogany casket and attendance by 5,000 mourners including aldermen and judges.

Decline and Assassination

Resistance to Bootlegging Opportunities

Colosimo's criminal enterprises, centered on , , and , had established a stable revenue stream by 1919, with estimates of over 100 brothels and numerous saloons under his influence in Chicago's district. The ratification of the 18th Amendment on January 16, 1919, and the enforcement of the on January 17, 1920, banned the manufacture, sale, and transportation of nationwide, immediately spawning lucrative bootlegging networks that could generate millions in illicit profits through , distilling, and speakeasies. Despite these opportunities, Colosimo resisted involvement, prioritizing the preservation of his existing vice operations over venturing into the volatile trade, which he perceived as carrying heightened risks of federal enforcement and violent competition from emerging gangs. His lieutenant, , who had been recruited from in 1909 to manage operations, repeatedly urged diversification into bootlegging, recognizing its potential to eclipse traditional rackets amid widespread public demand for . Colosimo's refusal stemmed from a combination of complacency with current earnings—reportedly sufficient to sustain his lavish lifestyle—and a strategic aversion to disrupting alliances with and politicians who tolerated his non- activities but might not extend the same leniency to violations. This stance ignored the economic shift underway, as bootlegging syndicates in cities like and began consolidating supply chains from and rural stills, offering scalable profits that dwarfed and yields. The discord escalated in early 1920, as Torrio, backed by associates including , pressed for expansion while Colosimo, recently remarried and focused on his Colosimo's Cafe nightclub, dismissed the proposals as unneeded. Colosimo's risk-averse approach, while rational from a first-mover perspective in trades, blinded him to the causal dynamics of : alcohol's cultural entrenchment ensured demand would outpace supply enforcement, creating a monopoly-like opportunity for organized groups willing to invest in violence and logistics. His intransigence not only forfeited market share to rivals but also strained internal loyalties, positioning bootlegging as a flashpoint for organizational realignment.

The Murder and Immediate Aftermath

On May 11, 1920, "Big Jim" Colosimo was assassinated inside his , Colosimo's Cafe, located at 2126 South Wabash Avenue in . He was shot twice in the head at close range by an assailant hiding in the as he entered the premises around 7:30 p.m., reportedly after receiving a urging him to return for an important shipment. The attack occurred in the lobby, and Colosimo died instantly at the scene without identifying his killer. Chicago police responded immediately, launching an investigation that included hundreds of tips but yielded no arrests or convictions, rendering the officially unsolved. Detectives theorized involvement by out-of-town gunmen, with early suspicion falling on Brooklyn mobster based on witness identifications and tips, though no charges followed. The probe highlighted Colosimo's extensive criminal ties but stalled amid the era's rampant corruption and limited forensic capabilities. In the immediate aftermath, Colosimo's associate assumed leadership of the organization, transitioning it toward Prohibition-era bootlegging operations. His funeral on May 15, 1920, drew thousands, including politicians and judges, in a featuring floral tributes and a silver , underscoring his influence in Chicago's vice economy. The event, estimated to cost $15,000, symbolized the unchecked power of figures at the time.

Theories and Unresolved Questions

The assassination of Vincenzo "Big Jim" Colosimo on May 11, 1920, remains officially unsolved, with no arrests or convictions despite immediate suspicions directed at organized crime figures. The primary theory, advanced by historians and mob chroniclers, posits that Colosimo's lieutenant, Johnny Torrio, orchestrated the hit to seize control of the organization and pivot it toward bootlegging under the newly enacted Volstead Act. Torrio, who had recruited associates from New York including Al Capone, reportedly grew frustrated with Colosimo's reluctance to expand into alcohol prohibition-era rackets, preferring to maintain focus on gambling, prostitution, and extortion. Circumstantial evidence includes Torrio's rapid assumption of leadership post-murder and the presence in Chicago that day of Frankie Yale, a Brooklyn gangster and Torrio associate, who allegedly pulled the trigger with two shots from a handgun in the vestibule of Colosimo's Cafe. Alternative theories point to personal motives tied to Colosimo's recent messy divorce from his first wife, Victoria Moresco, finalized amid allegations of infidelity and financial disputes. Police briefly suspected Moresco or her brother due to the timing, with reports of her receiving a suspicious phone call shortly before the shooting, though no direct evidence emerged. Some accounts speculate involvement by rival extortionists or disgruntled underlings, given Colosimo's history of internal clashes and his flashy lifestyle that bred envy, but these lack substantiation beyond contemporary rumors. Al Capone's role is occasionally hypothesized as the executor under Torrio's orders, leveraging his recent arrival from , yet this remains unsubstantiated and secondary to the Torrio-Yale narrative. Unresolved questions persist due to the era's systemic and limited forensic capabilities; the , infiltrated by gang influence, conducted a perfunctory yielding no witnesses or matches. from the .32-caliber used were inconclusive, and potential informants faced intimidation in a city where over 1,100 gang-related murders went unsolved during . Historians debate whether Colosimo's death marked a deliberate evolution or opportunistic power grab, as Torrio's subsequent expansion into suburbs and alliances with figures like the Genna brothers aligned with broader criminal adaptation to federal alcohol bans, but direct causal links rely on retrospective accounts from later Outfit members rather than contemporaneous proof. The absence of trial records or confessions leaves the precise motive—purely entrepreneurial or compounded by personal betrayals—open to interpretation, underscoring the opacity of early 20th-century underworld transitions.

Legacy and Historical Assessment

Foundation of the Chicago Outfit

Giacomo "Big Jim" Colosimo emerged as a pivotal figure in Chicago's underworld by consolidating fragmented Italian criminal activities into a structured operation during the early . Arriving in as a young immigrant from , , Colosimo initially engaged in extortion through the society before shifting focus to the lucrative trade in the Custom House Levee district. By the early , he had established control over a network of brothels, marrying madam Victoria Moresco to solidify his entry into the business under the political protection of alderman "Hinky Dink" . Colosimo's organization extended beyond prostitution to encompass illegal gambling and labor racketeering, centralizing authority over disparate pimps, thugs, and extortionists who previously operated independently. He achieved this by forming alliances with local political figures, providing payoffs in exchange for tolerance of his rackets, and organizing Italian street laborers into a union that doubled as a recruitment pool for enforcers. This structure marked the first significant unification of Chicago's Italian-American criminal elements, laying the operational foundation for what would evolve into the . His empire reportedly operated nearly 200 brothels and generated substantial revenue through vice monopolies in the district by the . To professionalize and expand his operations, Colosimo recruited from in 1909, initially as a and later entrusting him with managing the rackets. Torrio, leveraging his experience from Brooklyn's , introduced systematic enforcement and suburban expansion, including early investments in brewing facilities that foreshadowed -era opportunities. Although Colosimo resisted bootlegging, his pre-existing network of political connections, enforcers, and revenue streams provided the scaffold upon which Torrio built the Outfit's dominance after assuming control in 1920. Colosimo's death that year transitioned his loosely structured gang into a more hierarchical syndicate, retrospectively recognized as the Outfit's origins.

Economic Role in Prohibition Era Dynamics

Colosimo's pre- economic activities established a foundation in Chicago's vice economy, primarily through control of rings in the Levee district, where he operated or protected dozens of brothels, often leveraging his marriage to madam Victoria Moresco for operational efficiency. He supplemented this with gambling operations, extortion from local businesses, and saloon ownership, including an investment of $25,000 in a run by associate Jake "Greasy Thumb" Guzik, reflecting modest involvement in legal production. These rackets yielded reliable but constrained profits, estimated in the tens of thousands annually, sustained by alliances with corrupt politicians who granted protection in exchange for kickbacks. With the onset of under the effective January 17, 1920, national alcohol bans created a vast , transforming dynamics by shifting revenue potential from —previously capped by local demand and enforcement—to scalable bootlegging networks involving importation, , and distribution. Colosimo approved limited ventures, such as Johnny Torrio's plan to import liquor from on a small scale, but rejected broader commitments to bootlegging infrastructure, citing risks of intensified federal scrutiny and a preference for the lower-profile stability of his established enterprises. This stance contrasted with emerging opportunities, where bootlegging could generate millions through volume—far exceeding pre- margins—and integrate with existing saloons repurposed as . Colosimo's model exemplified the Prohibition era's transitional tensions, where pre-ban vice lords like him maintained territorial monopolies but failed to capitalize on 's prohibition-induced scarcity, which incentivized innovation in supply chains and violence for market control. His death on May 11, 1920, enabled Torrio to pivot the nascent toward aggressive bootlegging, illustrating how resistance to accelerated the of localized operations by industrialized empires that dominated the decade's criminal economy. This shift underscored causal dynamics wherein 's legal vacuum rewarded entrepreneurial risk-taking over conservative territorialism, elevating syndicates willing to navigate enforcement and .

Debates on Criminal Entrepreneurship vs. Exploitation

Colosimo's control over Chicago's Levee district vice operations, encompassing brothels, dens, and rackets, has prompted scholarly debate on whether his methods exemplified underworld or systemic . By 1914, he had consolidated disparate Italian immigrant street gangs into the city's first major Italian syndicate focused on and related activities, forging political alliances with aldermen such as Michael "Hinky Dink" Kenna and John "Bathhouse" Coughlin to bribe and secure operational stability. This organizational structure minimized chaotic turf wars, enabling a more predictable akin to legitimate business syndication, as noted in analyses of early 20th-century Italian crime networks in . Proponents of the entrepreneurial interpretation, drawing from historical accounts of vice economics, argue Colosimo innovated by treating vice as a : importing women for brothels, protecting operators via enforcers, and laundering profits through fronts like Colosimo's Cafe at 2126 South Wabash Avenue. Such efficiencies reportedly generated substantial income, funding expansions and influencing local governance through graft, which some criminologists view as adaptive responses to unregulated demand in immigrant enclaves where legal employment was scarce. Conversely, evidence of exploitation dominates critiques, particularly regarding , where Colosimo's network engaged in coercive practices labeled "" in federal probes under the 1910 . Operations involved kidnapping or deceiving young immigrant women—often from rural areas or abroad—into and forced sex work, with madams and enforcers maintaining control through violence and isolation, as detailed in contemporary surveys of Levee brothels. Raids in 1911-1912 targeted Colosimo directly, revealing systemic abuse that inflicted venereal disease epidemics and family breakdowns on vulnerable populations, prioritizing profit over consent. The tension persists in assessments: while Colosimo's model laid groundwork for later Outfit efficiency, reveals limited net societal value, as revenues derived primarily from coerced labor and victim harm rather than voluntary exchange, underscoring organized vice's parasitic dynamics over innovative enterprise.

Cultural Representations

Film and Television Portrayals

In the 1959 biographical film Al Capone, directed by Richard Wilson, Joe De Santis portrayed Big Jim Colosimo as the established Chicago vice lord whose reluctance to enter bootlegging sets the stage for his downfall and the rise of Al Capone. The depiction emphasizes Colosimo's control over prostitution and gambling rackets in the city's Levee District, culminating in his on-screen assassination ordered by Johnny Torrio. Frank Campanella played Colosimo in the 1975 gangster film Capone, directed by Steve Carver, where the character is shown as a flamboyant but outdated boss resistant to Prohibition-era opportunities, leading to his murder by associates including Capone. This portrayal highlights Colosimo's lavish lifestyle and his role in mentoring Torrio, drawing from historical accounts of the 1920 hit at his restaurant. On television, Frank Crudele depicted Colosimo in the HBO series Boardwalk Empire (2010–2014), appearing in Season 1 episodes such as "The Ivory Tower" and "Broadway Limited." Crudele, directed by Martin Scorsese in the pilot, portrayed him as a corpulent, opera-loving syndicate head negotiating with Atlantic City figures like Nucky Thompson, while underestimating threats from within his organization. The series accurately reflects Colosimo's historical murder on May 11, 1920, though it fictionalizes some alliances for dramatic effect. Peter Siragusa portrayed Colosimo in the 1993 pilot episode of the syndicated series The Untouchables, emphasizing his dominance in early 20th-century vice operations. Earlier TV episodes, such as in The Untouchables anthology series, referenced Colosimo's obsession with singer Dale Winter, mirroring real events that preceded his death. Colosimo's influence extends to indirect inspirations, such as the character Pete in the 1931 Little Caesar, directed by , modeled on his persona as a pimp-turned-gangster kingpin. Such representations often underscore his transition from District protector to Outfit founder, though later works prioritize his successors' narratives.

Music, Literature, and Gaming References

Colosimo features prominently in historical on organized crime, particularly as a foundational figure in the city's vice economy. Art Bilek's The First Vice Lord: Big Jim Colosimo and the Ladies of the (originally published 1994, revised edition 2019) details his rise from street-level operations to control of the District's prostitution and rackets, drawing on records, documents, and contemporary accounts to portray his consolidation of power in the early . James R. Ashley's When the Outfit Ran , Vol. I: The "Big Jim" Colosimo Era (2013) examines his leadership from approximately 1902 to 1920, emphasizing his role in organizing disparate Italian and Sicilian criminal elements into a proto-syndicate, supported by archival evidence of his alliances and territorial expansions. He is also referenced in Kenneth Allsop's The Bootleggers: The Story of 's Prohibition Era (1961), which contextualizes his pre-Prohibition activities as a precursor to the Outfit's bootlegging dominance. References to Colosimo in music are minimal and largely indirect, with no major songs or compositions dedicated to him identified in historical or discographic records. His personal affinity for and , as noted in biographical accounts of his lavish lifestyle, occasionally appears in narratives but does not extend to cultural tributes in the medium. In gaming, Colosimo's legacy manifests through locations and events inspired by his real-life enterprises. Watch Dogs (2014) includes Big Jim Colosimo's Café as a hotspot in its fictionalized setting, modeled after his historic Wabash Avenue restaurant opened in 1910, which served as a hub for vice figures. The Prohibition-era Bootleggers (2004) features an event card titled "Big Jim Colosimo Killed," referencing his 1920 and its impact on syndicate power shifts, with gameplay mechanics simulating news events that alter player territories.

References

  1. [1]
    One hundred years ago: Murder of 'Big Jim' Colosimo spawned one ...
    May 11, 2020 · One hundred years ago: Murder of 'Big Jim' Colosimo spawned one of the most powerful crime syndicates in American history – the Chicago Outfit.Missing: reliable sources
  2. [2]
    Giacomo "Big Jim" Colosimo - Boss of the Chicago Outfit and Brothel ...
    Giacomo “Big Jim” Colosimo was an Italian immigrant Mafioso who got his start as a pickpocket and went on to build the Chicago Outfit, that city's version ...Missing: founder | Show results with:founder
  3. [3]
    Big Jim Colosimo — Chicago's first crime boss - Chicago Tribune
    May 29, 2020 · Colosimo was gunned down in his restaurant on May 11, 1920. One theory has it that his second-in-command, Johnny Torrio, set up the killing.
  4. [4]
    Big Jim Colosimo: The Chicago Mob Boss Murdered In 1920
    Aug 18, 2025 · Also known as "Diamond Jim," Big Jim Colosimo served as the first boss of the Chicago Outfit until his murder on May 11, 1920, ...Missing: reliable sources
  5. [5]
    James Colosimo | Historica Wiki | Fandom
    Vincenzo Colosimo was born in Colosimi, Calabria, Italy on 16 February 1878, and he emigrated to the US city of Chicago, Illinois in 1895 at the age of 17.
  6. [6]
    James “Big Jim” Colosimo (1878-1920) - Find a Grave Memorial
    Early in his career he took up the Italian practice of sending Black Hand letters to wealthy citizens of Chicago. These anonymous messages threatened violence ...
  7. [7]
    Vincenzo Colosimo (1878–1920) - Ancestors Family Search
    Vincenzo Colosimo ( February 16, 1878 – May 11, 1920), known as James "Big Jim" Colosimo or as "Diamond Jim", was an Italian-American Mafia crime boss who ...
  8. [8]
    On May 11, 1920, mob boss, Vincenzo Colosimo, better known as ...
    May 11, 2025 · On May 11, 1920, mob boss, Vincenzo Colosimo, better known as James "Big Jim" Colosimo or as "Diamond Jim", was shot in an ambush & killed.Missing: reliable | Show results with:reliable
  9. [9]
    Flashback: Before Capone, there was Big Jim Colosimo: The father ...
    May 29, 2020 · His money had come from gambling operations and myriad brothels. In Colosimo's Cafe, judges and assistant state's attorneys dined and danced ...
  10. [10]
    Colosimo's - My Al Capone Museum
    Colosimo hired Torrio to help him out with his expanding businesses, roadhouses in Burnham and Chicago. by 1919, Prohibition was going to outlaw booze and ...<|control11|><|separator|>
  11. [11]
    IN THE BEGINNING… - Chicago Tribune
    Aug 26, 1997 · As a reward for his hard work, the aldermen named Colosimo as their official precinct captain. The fact that Colosimo also happened to marry ...Missing: payoffs | Show results with:payoffs
  12. [12]
    Chicago Stories | Al Capone's Bloody Business | Season 4 - PBS
    Nov 1, 2024 · By then, Yale's buddy Johnny Torrio was working in Chicago as the underboss for his uncle, Vincenzo Colosimo, better known as Big Jim. - He ...
  13. [13]
    Johnny Torrio | Biography & Al Capone - Britannica
    Torrio had moved from New York to Chicago in 1909 to help run the giant brothel business under Chicago crime boss Big Jim Colosimo. Shortly after Capone's ...Missing: recruitment | Show results with:recruitment
  14. [14]
    Giovanni “Johnny” Torrio – Presiding Over the Chicago Outfit
    It was during this time that he recruited Al Capone. In the meantime, Torrio had become involved with his uncle, Giacomo “Big Jim” Colosimo, a major crime boss ...
  15. [15]
    Jim Colosimo, the Infamous Crime Boss Who Tied the Knot at West ...
    Oct 3, 2019 · Jim grew up shining shoes and selling newspapers on the streets of Chicago to help his immigrant family eat. He worked as a street sweeper and ...Missing: sources | Show results with:sources
  16. [16]
    How Did Big Jim Colosimo Get Killed? - Chicago Outfit
    Feb 7, 2025 · Even though he was assassinated in 1920, the cafe was still open for another 35-40 years, running under the same name. Colosimos. Inside ...<|control11|><|separator|>
  17. [17]
    Colosimo, Vincenzo "Jim" (1878-1920)
    Colosimo, perhaps fearing to compete with established underworld gangs in the import of alcohol, reportedly refused. Colosimo was assassinated May 11, 1920.
  18. [18]
    BIG JIM GOES TO THE GRAVE - American Hauntings
    May 14, 2014 · Big Jim Colosimo owned two large brothels in the district: the Victoria and the Saratoga. The Victoria was named in honor of Colosimo's wife, ...
  19. [19]
    [PDF] Chapter XXV: Funerals of Gangsters
    "Following the body of Big Jim Colosimo to the grave today will move a cortege which should interrupt the complacent thought of Chi- cago. Three judges, eight ...
  20. [20]
    THE GANGS OF PROHIBITION-ERA CHICAGO 6 - Nomos eLibrary
    ... Colosimo's murder in May 1920. Their alliance was shaky and only temporary ... Over 1,100 unsolved murders attributed to organized crime gangs in ...
  21. [21]
    The Chicago Outfit: Challenging the Myths About Organized Crime
    Although they were suspected in numerous murders, few (if any) members of the Outfit—or the bootlegging gangs that preceded it—were convicted of a homicide ...
  22. [22]
    Al Capone's Bloody Business | Chicago Stories - WTTW
    An Italian-American crime syndicate first established by “Big Jim” Colosimo at the turn of the century, the Outfit amassed an estimated $100 million in revenue ...
  23. [23]
    How Chicago Became a Bootlegging Capital | eATLAS
    Jan 4, 2024 · Although he was also anti-Prohibition, he understood the domino effect the gang wars were having on the city. He took steps to clean up the city ...
  24. [24]
    The Beer Wars and Al Capone's Bloody Business - Chicago - WTTW
    Gangsters such as James “Big Jim” Colosimo – who led a gang that would eventually become the Chicago Outfit – earned their profits from gambling, prostitution, ...Missing: saloons | Show results with:saloons
  25. [25]
    Prohibition Profits Transformed the Mob
    Torrio, who toiled under brothel racketeer Big Jim Colosimo before 1920, had Colosimo killed after the boss refused his pleas to get into bootlegging. The ...
  26. [26]
    Prohibition Examined: Chapter III - Life & Thyme
    Mar 20, 2018 · When the National Prohibition Act passed in 1919, Colosimo wanted no part of the illegal liquor trade, something Torrio was convinced could ...
  27. [27]
    Bootleggers, Bathtub Gin, & Speakeasies: Organized Crime in the ...
    Dec 3, 2022 · He owned thousands of speakeasies. He led illegal brewery, distillery, and distribution operations and made tens of millions of dollars each ...
  28. [28]
    Italians and Crime in Chicago: The Formative Years, 1890-1920 - jstor
    ABSTRACT. To most contemporaries in the period to 1921, Italian crime in the United States and specifically Chicago meant the Black Hand or Mafia.
  29. [29]
    [PDF] Organized Crime in Chicago : Beyond the Mafia - Squarespace
    I later found out that he was a member of the North Side Crew of the Chicago Outfit, the traditional organized crime group in Chicago. Growing up in the West.
  30. [30]
    [PDF] Chapter XVIII: the Exploitation of Prostitution
    At the head were "Big Jim" Colosimo, the "brains," and his ... The Exploitation of Prostitution or connected by passages with, clandestine flats and houses of ...<|separator|>
  31. [31]
    (PDF) On the importance of being John Landesco - ResearchGate
    Apr 14, 2020 · In the field of organized crime, John Landesco is best known for his 1929 study titled “Organized Crime in Chicago,” published as part of the ...
  32. [32]
    Frank Crudele Movies and Shows - Apple TV
    He has played prominent roles in both film & television and was chosen and directed by Martin Scorsese to play “Big Jim Colosimo” in the 2009 pilot episode ...
  33. [33]
    No Witness, No Case/Poor Edith - IMDb
    Gangland boss Jim Colosimo is obsessed with singer Dale Winter so hires Johnny Torrio and Al Capone to deal with business. In 1911, James Bingham is caretaker ...
  34. [34]
    Little Caesar | Research Starters - EBSCO
    Pete Montana (Ralph Ince) was modeled on “Big Jim” Colosimo, known as the “King of the Pimps,” and the “Big Boy” (Sidney Blackmer) was based upon corrupt ...
  35. [35]
    The First Vice Lord: Big Jim Colosemo and the Ladies of the Levee
    THE FIRST VICE LORD is the story of the life and death of Big Jim Colosimo and Chicago's infamous segregated red-light district--the Levee.
  36. [36]
    https://www.kobo.com/ww/en/ebook/when-the-outfit-ran-chicago-vol-i-the-big-jim-colosimo-era
  37. [37]
    Profile for James "Big Jim" Colosimo from The Bootleggers: The ...
    James Big Jim Colosimo has appeared in the following books: The Bootleggers: The Story of Chicago's Prohibition Era.
  38. [38]
    Episode 40: The Chicago Outfit- Jim Colosimo - YouTube
    Apr 20, 2021 · In this episode, we discuss Chicago's original gangster: "Big Jim" Colosimo. Colosimo was a powerful kingpin with an interest in life's finerMissing: television appearances
  39. [39]
    Big Jim and Showdown in Gangland - BoardGameGeek
    Feb 27, 2023 · For Big Jim Colosimo Killed (News) it states "When this card is revealed, place 1 Speakeasy marker on each Neighborhood with 2 Business markers ...