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Angelo "Bloody Angelo" Genna (Italian pronunciation: [ˈandʒelo ˈdʒɛnna]; February 3, 1898 – May 26, 1925) was an Italian-born Chicago bootlegger and organized crime leader during the Prohibition era. A key member of the Sicilian crime family, primarily made up of his brothers, he was best known for his war with the North Side Gang leader, Dean O'Banion.

Key Information

Genna and his brothers then fought the North Side's new leader, George "Bugs" Moran. But, almost seven months later, in May 1925, Moran chased Angelo in a high-speed car chase and shot him to death. In June and July, two of Angelo's brothers were killed, while the other three brothers fled.

Early life

[edit]

Angelo Genna was born on February 3, 1898, in Marsala, Sicily. Genna's parents, Antonino Genna Sr. and Maria Concetta Utica, had six other sons: Antonio "the Gentleman", Mike "the Devil", Vincenzo "Jim", Pietro "Peter", Salvatore "Sam", and Nicola Genna (who stayed in Sicily); and two daughters: Rosa Laudicina and Caterina Mariana.[1][unreliable source?] He and his brothers entered the U.S. through New York around 1910. Angelo arrived in New York harbor on August 5, 1914, via the S.S. Venezia. He was on his way to meet his brother Pietro, who lived at 870 Blue Island Avenue in Chicago.[2][unreliable source?]

Aldermen's Wars

[edit]

The Aldermen's Wars were at their height at the time of the 19th Ward's 1921 elections. Anthony D'Andrea hired Genna to kill supporters of alderman John Powers. Genna was suspected of killing Harry Raimondi and Paul Labriola, two Powers supporters that won the elections.

Genna was arrested and tried for the murder of Labriola. His defense attorney was a friend of D'Andrea. In 1922, Genna was prosecuted for the murder of Paul Notti, who had identified Genna on his deathbed. Genna was not convicted on either charge. In November 1922, Genna was sentenced to a year in prison after being convicted for the prostitution of a 15-year-old girl.[3][better source needed]

On December 18, 1922, Genna was arrested by detectives after being named as a stolen goods fence for a gang accused of killing Joe Lanus. He is then released on $15,000 bonds.[1]

Prohibition and O'Banion

[edit]

The Gennas became a close knit Marsala-based Mafia and bootlegging gang. In 1919, the Gennas obtained a federal license to legally manufacture industrial alcohol, which they sold illegally. Angelo and his brothers operated from Chicago's Little Italy, which was located west of the Chicago Loop.[3]

They started selling their extra alcohol at cut-rate prices outside of their territory. This caused a problem with the North Side Gang leader Dean O'Banion, who went to John "Johnny The Fox" Torrio and Unione Siciliana boss Mike Merlo to get the Gennas to back down. When Torrio refused, O'Banion began hijacking shipments of alcohol belonging to the Genna brothers.

On November 3, 1924, Dean O'Banion inadvertently signed his own death warrant during an argumentative phone call to arch-rival Angelo Genna. Their disagreement originated at The Ship, the gambling casino that the North Side gang boss owned along with the Torrio Syndicate. On this day, O'Banion sat in with Al Capone, Frank Nitti, Frank Rio, and others to tally the week's profits. It was mentioned that Angelo Genna had dropped a large amount of cash, plus a sizable marker. Capone recommended that they cancel the marker as a professional courtesy. O'Banion, instead, got Genna on the telephone and demanded that he pay his debt within a week. With this personal insult, Angelo Genna and his family could no longer be restrained.[4] Until then, Merlo and the Unione had refused to sanction a hit on O'Banion. However, Merlo had terminal cancer and died on November 8, 1924. With Merlo gone, the Gennas and South Siders were free to move on O'Banion.

Hitmen working on orders from Torrio and the Gennas killed O'Banion on November 10, 1924.[3] Francesco Yale and two Genna hitmen—John Scalise and Alberto Anselmi—entered O'Banion's flower shop, Schofield, and when Yale and O'Banion shook hands, Scalise and Anselmi shot two bullets into O'Banion's chest and two in his throat, and one of them shot a final bullet into the back of his skull as he was lying on the floor, face-down.[5]

Personal life

[edit]

On December 13, 1922, Angelo and Lucille Spingola applied for a marriage license and on January 10, 1923, Angelo and Lucille got married. Spingola was the sister of Genna ally Peter Spingola. The wedding was lavish, with 3,000 guests and a 2,000 pound cake.[2][unreliable source?]

Gang war and death

[edit]

After the O'Banion hit, Chicago erupted into a five-year full-scale war. The North Siders—now led by Hymie Weiss—attempted to assassinate Torrio outside his home, causing Torrio to flee to Italy, leaving his second-in-command—Alphonse "Scarface" Capone—as head of the Chicago Outfit.[3]

The North Siders took aim at the Genna brothers. On May 26, 1925, Moran, Vincent "The Schemer" Drucci, and Hymie Weiss shot and wounded Genna numerous times during a high-speed car chase, causing Genna to crash his car into a lamp post at Hudson and Ogden Avenues. Angelo was rushed to the Evangelical Deaconess Hospital. When police asked Genna who shot him, he merely shrugged. He died shortly afterwards while his brother Sam, wife, and brother-in-law were at his bedside. He was buried on May 29, 1925, at the Mount Carmel Cemetery in Chicago.[2][unreliable source?]

Funeral

[edit]

Several hundred people attended Genna's funeral on May 29, 1925. His funeral was supposed to belittle O'Banion's previous $100,000 funeral. Genna was laid out in a $3,000 bronze coffin that weighed about 1,200 pounds and was surrounded by $75,000 worth of flowers, mostly bought from O'Banion's flower shop Schofield. Capone had sent lilies, Joseph "Diamond Joe" Esposito sent peonies, Torrio sent a huge vase of pink and white carnations. There was also a floral tribute sent from Samuzzo Amatuna.[1]

The funeral home in which his funeral took place—Michael Larussi's Undertaking Establishment—was filled with pallbearers and members of Unione Siciliana. Included in mass of people were 50 policemen, politicians, lawyers, doctors, and labor union officials.

Aftermath

[edit]

On June 13, 1925, Mike Genna was shot by police after a shootout with North Siders. On July 8, 1925, Antonio Genna was ambushed and shot to death. The remaining three brothers Jim, Sam, and Peter fled Chicago.[3]

References

[edit]
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Angelo Genna

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Angelo "Bloody Angelo" Genna (February 3, 1898 – May 26, 1925) was a Sicilian-born who rose to prominence as a leader of the in Prohibition-era , overseeing bootlegging operations and violent enforcement against rivals. Born in , , to Antonino and Mary Genna, he immigrated with his five brothers—Peter, Jim, Sam, Tony, and Mike—and initially engaged in extortion as part of a Black Hand gang before shifting to large-scale alcohol importation and distribution during the Volstead Act's enforcement starting in 1920. The Genna brothers, dubbed the "Terrible Gennas" for their brutality, established headquarters in a West Side and amassed wealth by supplying whiskey to speakeasies, often allying with Johnny Torrio's organization while clashing with Irish gangs like Dean O'Banion's North Siders over territory and the Unione Siciliana leadership. Their operations fueled intense gang warfare, marked by ambushes and assassinations, culminating in Angelo's fatal wounding during a high-speed pursuit by North Side gunmen and on May 26, 1925, when he crashed his vehicle into a lamppost after sustaining multiple gunshot wounds. At age 27, his death precipitated further losses for the , weakening their hold on 's underworld amid escalating violence that claimed several brothers in quick succession.

Early Life

Birth and Family Background

Angelo Genna was born on February 3, 1898, in , province, , . He was the son of Antonino Genna Sr. and Maria Concetta Utica. The Gennas originated from , where the family resided prior to emigration. Angelo had five brothers—Peter, Sam, (known as Jim), Mike (nicknamed "The Devil"), and (called "The Gentleman")—who together formed the nucleus of the Genna crime syndicate in . The brothers also had sisters, including Rosa Laudicina and Caterina Mariana.

Immigration and Settlement in Chicago

Angelo Genna was born on , 1898, in Marsala, , to a family of six brothers who would later become notorious in American . The Genna brothers emigrated from to the between 1906 and 1914, initially posing as farm hands upon entry. Several brothers, including Peter, arrived earlier and established themselves in by around 1910, settling in the Taylor Street area of the city's neighborhood, a densely populated Sicilian enclave known as Little Sicily. Angelo himself arrived in on August 5, 1914, aboard the S.S. Venezia, before proceeding to join his siblings in . The family initially resided in the working-class immigrant community, where Sicilian traditions and networks facilitated their integration, though economic pressures in the urban environment soon drew them toward illicit opportunities. By the mid-1910s, the Genns had formed a tight-knit operation in Little Sicily, leveraging ethnic ties for protection and business amid the challenges of early 20th-century urban .

Criminal Ascendancy

Initial Involvement in Extortion and Black Hand Activities

Upon arriving in Chicago around 1910 with his brothers, Angelo Genna, the youngest of the six Genna siblings born in Sicily, played a pivotal role in the family's entry into organized crime through Black Hand extortion rackets. These schemes targeted prosperous Italian immigrants and businessmen in neighborhoods like Little Italy's "The Patch," where the Genns settled, using anonymous threatening letters emblazoned with a black hand symbol to demand payments under penalty of violence, arson, or bombings. Angelo, recognized for his aggressive temperament, is credited with orchestrating the brothers' inaugural extortion operations, which capitalized on the pervasive fear among Sicilian expatriates vulnerable to such intimidation tactics prevalent in early 20th-century Chicago. The Black Hand method, not a but a loose practice imported from , involved mailing demands for sums ranging from hundreds to thousands of dollars, often escalating to physical threats or explosive devices if unmet; recorded dozens of such incidents annually in the , including 55 bombings in the first half of alone. The Genna brothers' involvement allowed them to extract protection money from local merchants and professionals, establishing a foundation of illicit revenue before Prohibition's onset in shifted their focus toward alcohol trafficking. While police investigations into these rackets rarely yielded convictions due to victim reluctance to cooperate—stemming from cultural distrust of authorities and fear of retaliation—no direct arrests tied or his brothers to specific Black Hand cases during this period, though their reputation for ruthlessness grew. This early phase honed the family's operational tactics, blending with ethnic solidarity to dominate in Italian enclaves.

Participation in the Aldermen's Wars

Angelo Genna emerged as a key enforcer for during the Aldermen's Wars, a series of violent clashes in Chicago's 19th Ward between 1916 and 1921 pitting Italian interests led by D'Andrea against Irish alderman John "Johnny de Pow" Powers. The Genna brothers, including Angelo, backed D'Andrea's campaigns for aldermanic office, engaging in intimidation, bombings, and assassinations targeting Powers' supporters and precinct captains to secure Italian dominance in the ward's politics. Genna's involvement included direct participation in murders linked to the feud, such as the February 21, 1916, killing of Frank Lombardi, a Powers ally, amid D'Andrea's initial unsuccessful run against James Bowler, where D'Andrea garnered 1,753 votes to Bowler's 4,163. By the height of the wars during the 1921 elections, Genna was reportedly hired by D'Andrea to eliminate opponents, with suspicions falling on him for the deaths of Harry Raimondi and Paul Labriola, Powers' backers. The conflict escalated with kidnappings and shootings on , April 5, 1921, enabling Powers to narrowly win by 381 votes, followed by D'Andrea's on May 10, 1921, at 902 S. Ashland Avenue. The wars resulted in over 30 murders, yet only one led to prosecution: that of Angelo Genna for a killing during the violence, highlighting the impunity enjoyed by participants amid widespread corruption and ethnic rivalries. Following D'Andrea's death on May 12, 1921, the Genna brothers assumed greater control over Little Italy's rackets, transitioning from political enforcement to broader extortion and bootlegging operations.

Prohibition-Era Operations

Bootlegging Empire and Genna Brothers Syndicate

The Genna brothers established their bootlegging operations in Chicago's neighborhood shortly after the onset of national in January 1920, leveraging a federal license obtained in 1919 to legally produce industrial alcohol, which they diverted and redistilled into potable spirits for illegal sale. This permitted them to supply high volumes of low-cost liquor to speakeasies and allied gangs, initially as members of Torrio's beer and alcohol , where they agreed to restrict sales to their designated west-side territory. By 1923, however, they had expanded distribution beyond these boundaries, supplying distilled spirits directly to the Torrio-Capone syndicate using police escorts and intermediaries to evade raids. Central to their empire was a decentralized cottage industry model, involving the installation of thousands of small, one-gallon copper stills in tenement apartments across , operated by impoverished Italian immigrant families recruited as "alky cookers." The brothers furnished these operators with corn mash, sugar, yeast, and production instructions, compensating them approximately $15 per day while collecting the output weekly; this method yielded low-quality but inexpensive alcohol at a production cost of 50 to 75 cents per gallon, which they wholesaled to speakeasies for $6 per gallon. The dispersed nature of the stills—scattered among homes rather than concentrated in large facilities—made federal and local enforcement efforts largely ineffective, as authorities struggled to dismantle the network without widespread community complicity. The scale of operations generated substantial revenue, estimated at $350,000 monthly or $4.2 million annually by the mid-1920s, with profits reaching $1.8 million per year and the brothers' collective wealth totaling around $5 million by 1924. Known as the "Terrible Gennas," the six brothers—Peter, Sam, Jim, Tony, Angelo, and Mike—coordinated the syndicate from a disguised headquarters posing as an olive oil and cheese import business on West Taylor Street, enforcing discipline through violence and corrupting local officials via the Unione Siciliana mutual aid society. Angelo Genna, often called "Bloody Angelo" for his ruthless enforcement, played a pivotal role in organizing the alky-cooking workforce and intimidating rivals or defectors, solidifying the family's control over west-side liquor production and distribution until territorial encroachments sparked deadly conflicts with the North Side Gang.

Corruption of the Unione Siciliana

The Unione Siciliana, established in Chicago in 1895 as a fraternal benevolent society for Sicilian immigrants, fell under the influence of organized crime figures during the Prohibition era, with the Genna brothers playing a pivotal role in its corruption. Following the death of its incumbent president Mike Merlo from cancer on November 8, 1924, Angelo Genna ascended to the presidency by early 1925, leveraging the organization's structure to advance the Genna syndicate's bootlegging and extortion rackets. Under Genna control, the Unione shifted from providing mutual aid and cultural support to serving as a front for Mafia operations, enabling the brothers to exert authority over Little Italy's Sicilian community through intimidation and selective patronage. Angelo Genna's volatile leadership intensified the organization's criminal entrenchment, as the Gennas reportedly initiated its transformation into an arm of emerging national networks, using membership rolls to identify targets and coordinate illegal alcohol distribution alliances with figures like . This period saw the Unione weaponized in power struggles, with Genna's presidency—lasting mere months—marked by heightened violence, including retaliatory killings tied to disputes over and tribute payments from speakeasies. The brothers' dominance allowed them to install loyalists in key positions, diverting nominal dues and event proceeds toward syndicate coffers rather than charitable ends. Genna's on May 26, 1925, during a high-speed police chase, exposed the depth of the , as his triggered immediate factional infighting for Unione control, underscoring how the Gennas had prioritized criminal utility over the society's original fraternal mission. Surviving brothers like Peter and Sam briefly retained influence before fleeing to , ending their roughly six-month reign over the organization and paving the way for further bloodshed among rivals like Samuzzo Amatuna. This episode exemplified the causal shift from community welfare to , where leadership transitions were enforced by rather than election, eroding any remnants of legitimacy.

Rivalries and Gang Conflicts

Clashes with Dean O'Banion and the North Side Gang

The Genna Brothers, including Angelo, engaged in territorial disputes with Dean O'Banion's North Side Gang over bootlegging operations in Chicago's Near North Side during the early 1920s, as the Gennas expanded their alcohol distribution from Little Italy into areas controlled by O'Banion's predominantly Irish outfit. O'Banion's gang responded by hijacking Genna liquor shipments, escalating tensions that contributed to broader conflicts between North Side Irish factions and South Side Italian groups allied with the Gennas. Following the death of Unione Siciliana president on November 8, 1924, the Gennas, aligned with and , reportedly facilitated the assassination of O'Banion two days later on November 10, 1924, at his flower shop on North State Street, using gunmen such as Albert Anselmi and John Scalisi to execute the hit amid disputes over Unione control and bootlegging rights. O'Banion's murder, attributed by North Siders to Genna involvement, ignited retaliatory violence, with assuming leadership of the and targeting the Genna syndicate as proxies for Torrio-Capone retribution. On May 26, 1925, Angelo Genna, known as "Bloody Angelo" for his enforcer role, was killed in a high-speed automobile pursuit initiated by North Side gunmen including , , and , who fired multiple shots into his vehicle near Ogden Avenue and Hudson Street, causing it to crash into a lamppost; Genna succumbed to his wounds shortly after. This , occurring while Genna drove to make a house payment, was viewed by authorities and contemporaries as direct vengeance for O'Banion's slaying, further weakening the Genna operation as subsequent attacks claimed brothers Mike on June 13 and Tony on July 8, 1925. The clashes underscored ethnic and territorial fault lines in Chicago's underworld, with the Gennas' aggressive expansion provoking sustained North Side reprisals that dismantled their syndicate by mid-1925.

Alliances, Betrayals, and Escalating Violence

The Genna Brothers, led prominently by Angelo, forged a strategic alliance with the under and , supplying high-volume alcohol from their clandestine West Side distilleries to Outfit operations while coordinating against mutual threats from Irish-dominated gangs. This partnership extended to control of the Unione Siciliana, a fraternal organization of Sicilian immigrants that served as a vehicle for political influence and dispute resolution within Chicago's Italian underworld; following the death of president on November 8, 1924, Angelo Genna assumed the presidency on November 11, leveraging it to consolidate power and block non-Sicilian encroachments. The alliance provided the Gennas with protection and market access, but their aggressive territorial expansion in strained Torrio's preference for negotiated truces, as the brothers' frequent resort to bombings and executions drew unwanted police scrutiny and escalated inter-gang hostilities. Key betrayals intensified the rift with Dean O'Banion's , whose hijackings of Genna liquor convoys—estimated at dozens of truckloads in 1923–1924—undermined the fragile bootlegging peace brokered by Torrio. O'Banion's maneuvers, including his double-cross in the 1924 Sieben Brewery deal where he sold the site to Torrio only to tip off federal agents for a raid, implicated the entire alliance and prompted retaliatory plotting; Angelo Genna, as Unione head, reportedly endorsed or facilitated the November 10, 1924, of O'Banion at his flower shop, viewing the Irish bootlegger's bid for Unione presidency as a direct affront to Sicilian autonomy. Such acts of treachery, rooted in O'Banion's opportunistic raids and ethnic power grabs, eroded any pretense of coexistence, with Genna's inner circle—including enforcers like Vincenzo De Mora—allegedly providing logistical support for the hit to safeguard Outfit interests. This cycle fueled escalating violence across Chicago's underworld, marked by a surge in targeted shootings and ambushes from late 1924 onward. Post-O'Banion, North Side successors , , and retaliated by machine-gunning Torrio outside his home on January 24, 1925, leaving him critically wounded and prompting his retreat from active leadership; the Gennas, exposed without Torrio's mediation, faced intensified assaults, including drive-by attacks on their Taylor Street . Angelo Genna's personal belligerence amplified the bloodshed, with his outfit linked to at least five murders in 1924 alone, often executed via sawed-off shotguns in broad daylight to terrorize rivals; by spring 1925, the violence claimed three Genna brothers in rapid succession—Angelo on May 26 after a high-speed pursuit, followed by Mike and Pete—dismantling their syndicate and forcing survivors to disband or flee, as Capone absorbed remnants into the Outfit. These events, totaling over 100 gang-related killings in by mid-1925, underscored the Gennas' role in shifting from opportunistic to full-scale territorial warfare, prioritizing dominance over alliance stability.

Personal Life

Marriage and Immediate Family

Angelo Genna married Lucia Domenica "Lucille" Spingola on January 10, 1925, in , . The union linked Genna to the Spingola family, as Lucille was the sister of Peter Spingola, a associate and ally in bootlegging operations. The wedding featured extravagant elements, including a $2,000 cake made with 400 pounds of sugar, 400 pounds of flour, seven cases of eggs, and 50 pounds of butter, and drew approximately 3,000 guests. The couple had no children, as Genna was killed less than five months later on , 1925. Lucille Spingola, born in 1903, later remarried Charles Albert Spiziri and died in 1969. Genna's immediate family originated from the Sicilian village of ; he was one of at least seven sons born to Antonino Genna Sr. and Maria Concetta Utica, including brothers Antonio "Tony," Mike "The Devil," Vincenzo "Jim," "Peter," and Sam, several of whom formed the core of the Genna crime syndicate.

Lifestyle, Associates, and Daily Operations

Angelo Genna exhibited a volatile and superstitious personality, characterized by hot-headedness and a readiness to resort to violence, traits that earned him the moniker "Bloody Angelo." He resided in Chicago's , the epicenter of the Genna syndicate's activities, where the brothers leveraged their criminal profits for a relatively lavish existence amid ongoing threats from rivals. His primary associates were his five brothers—Mike, Tony, Sam, Peter, and Jim—who formed the tight-knit core of the , operating as a Sicilian faction independent yet initially allied with elements of the under and . Genna also maintained connections within the Unione Siciliana, collaborating with figures like to consolidate influence among Sicilian immigrants. These relationships facilitated enforcement through hired gunmen and extended the syndicate's reach into gambling and rackets. Daily operations centered on managing the bootlegging empire, which involved supervising clandestine distilleries hidden in basements and warehouses, sourcing sugar for industrial-scale production, and distributing illicit alcohol via a network of Italian laborers and enforcers. Genna's routine likely included armed patrols, meetings with suppliers and underlings in local cafes or social clubs, and resolving disputes through intimidation or assassination to protect territorial interests against incursions.

Assassination

Prelude to the Fatal Chase

In the wake of Dion O'Banion's murder on November 10, 1924, which the North Side Gang attributed to the Genna brothers and their allies in the Chicago Outfit under Johnny Torrio and Al Capone, tensions escalated into open warfare over bootlegging territories and control of the Unione Siciliana. The Gennas, who had gained influence in the Unione following Mike Merlo's death, were seen as key perpetrators in O'Banion's slaying due to their Sicilian faction's rivalry with the Irish-dominated North Siders. Hymie Weiss, assuming leadership of the North Side after O'Banion, along with George "Bugs" Moran and Vincent "Schemer" Drucci, vowed systematic retaliation against the Genna syndicate, targeting its members to disrupt their operations and avenge their fallen leader. This vendetta was fueled by broader ethnic and territorial animosities, with the North Siders viewing the Gennas' aggressive expansion in Little Italy as a direct threat to their North Side liquor rackets. Angelo Genna, known for his violent reputation and prior involvement in gangland killings such as those of Paul Labriola and possibly others tied to Unione disputes, emerged as a prime target due to his role in the brothers' enforcer activities and his push for greater Unione control. By spring 1925, intelligence from North Side operatives likely tracked Genna's routines, including his residences and daily movements between his apartment and West Side operations, setting the stage for an opportunistic . On the morning of May 26, 1925, as Genna drove southbound on Ogden Avenue with his brother Pete, the North Side hit team—comprising Moran, Drucci, and at least one other gunman armed with sawed-off shotguns—intercepted him near Hudson Avenue, initiating the pursuit that would prove fatal. This strike was part of a calculated campaign to dismantle the Genna family's influence, reflecting the North Siders' strategy of mobile, high-risk hits amid Chicago's intensifying Prohibition-era conflicts.

The Shooting and Death

On May 26, 1925, at approximately 9:30 a.m., Angelo Genna was driving southbound on Ogden Avenue in when he was ambushed by gunmen in a pursuing . The attackers, numbering four and armed with shotguns, fired multiple blasts into Genna's vehicle during a high-speed chase reaching speeds of up to 60 miles per hour, striking him numerous times in the head, neck, and body. Genna lost control of his car and crashed into a lamppost at the intersection of Ogden and Hudson Avenues. Bleeding profusely but initially conscious, Genna was rushed to Cook County Hospital, where he succumbed to his gunshot wounds a few hours later. The assailants escaped in their vehicle, and no arrests were immediately made, though police and contemporary accounts attributed the hit to members of the , including , , and Vincent "Schemer" Drucci, amid escalating bootlegging rivalries following the murder of . The shooting marked a significant escalation in Chicago's gang warfare, with Genna, at age 27, becoming one of the first major Genna brothers to fall to targeted violence rather than . details confirmed death by multiple wounds, consistent with the close-range tactics prevalent in Prohibition-era hits.

Funeral and Immediate Aftermath

Funeral Proceedings

Angelo Genna's funeral proceedings were marked by extravagance intended to surpass the scale of previous funerals, such as that of , reflecting the Genna family's influence within Chicago's underworld and the Unione Siciliana. Roman Catholic authorities denied church burial rites due to Genna's notorious criminal activities, leading to a wake held at his in-laws' home on Taylor Street near instead. The body, weighing 195 pounds and dressed in a royal purple robe, was placed in a $6,000 casket weighing 1,200 pounds. The procession to Cemetery in , on May 29, 1925, featured a mile-and-a-half-long cortege with 31 limousines laden with floral tributes, accompanied by a marching band. Floral arrangements, valued at $75,000 and primarily supplied by Schofield’s florist, included tributes from key figures such as (lilies), (pink and white carnations), "Diamond Joe" Esposito (peonies), and Samoots Ammatuna; thirty automobiles transported these flowers to the gravesite. An estimated 20,000 people lined the streets of to observe the event, which drew attendees including several hundred mourners, Unione Siciliana members serving as pallbearers, politicians, lawyers, doctors, labor union officials, judges, and federal officials. Genna was initially interred in a $10,000 temporary vault near Dean O'Banion's gravesite, with fifty policemen managing traffic and crowd control along Taylor Street, where proceedings blocked access starting at 10:00 a.m. The body was later transferred to the Genna family at the same cemetery.

Short-Term Repercussions for Associates

Following Angelo Genna's assassination on May 25, 1925, the experienced a cascade of retaliatory violence from the , resulting in the deaths of two more brothers within weeks. Mike Genna was gunned down on June 13, 1925, during a chaotic with police and North Side gunmen near Ogden Avenue and Van Buren Street, where he fired over 60 shots before succumbing to wounds. This incident, dubbed the "Day of Sixty Shots," highlighted the escalating chaos and directly weakened the family's operational capacity, as Mike had been a key enforcer in their bootlegging . Antonio "Tony" Genna met a similar fate on July 8, 1925, when ambushed and killed by North Side assassins in a , marking the third Genna brother slain in under two months. These losses prompted the surviving brothers—Peter, Jim, and Sam—to temporarily flee for , disrupting their territorial control in and exposing vulnerabilities among lower-level associates. Internal betrayals compounded the fallout, with Genna-sponsored loyalists such as Joseph Spano turning informant or defecting to rivals, accelerating the erosion of trust and cohesion within the organization. The rapid decapitation of leadership shifted power dynamics, enabling Al Capone's to absorb former Genna bootlegging routes and distilleries with minimal resistance, as associates scrambled to realign allegiances amid the power vacuum. By early , this instability extended to family extensions, including the murder of Angelo's brother-in-law Henry Spignola on January 10, , further deterring prospective allies and forcing remnants to operate underground or seek protection under Capone.

Legacy

Decline of the Genna Crime Family

Following the assassination of Angelo Genna on May 26, 1925, the Genna crime family suffered rapid successive losses that eroded its operational capacity and territorial control in Chicago's Little Italy. Mike Genna was killed on June 13, 1925, during a shootout with police officers allied with North Side gang elements, marking the second major blow within weeks. Antonio Genna met a similar fate on July 8, 1925, when ambushed and fatally shot by assailants linked to the North Side faction amid escalating bootlegging rivalries. These killings, attributed to reprisals from the North Side gang following the Genna brothers' involvement in the murder of Dean O'Banion in November 1924, decapitated the family's leadership and prompted the surviving brothers—Jim, Sam, and Peter—to flee Chicago for safety. The exodus of the remaining Genna leaders left their bootlegging network, which had relied on Sicilian immigrant labor and control of the Unione Siciliana for enforcement, vulnerable to absorption by Al Capone's . By mid-1925, the Outfit had consolidated power over former Genna territories in the Near West Side, integrating surviving operatives and redistributing alcohol rackets without resistance from a fragmented Genna remnant. Although the fleeing brothers later returned to the Chicago area in subdued capacities—engaging in low-profile activities rather than —the family's independent structure dissolved, with no resurgence of its prior influence in Prohibition-era underworld dynamics. Peter Genna, for instance, lived until May 13, 1948, dying of natural causes at age 67, while Sam survived until 1951, underscoring the permanent shift from active gang warfare to marginal existence. This decline exemplified the causal fragility of family-based syndicates in Chicago's gangland, where the loss of multiple enforcers in quick succession—without robust succession mechanisms—enabled larger alliances like the Outfit to dominate through superior manpower and strategic alliances. The Genn'as earlier aggression, including territorial encroachments that provoked the North Siders, directly precipitated their downfall, as retaliatory strikes exploited internal dependencies on fraternal loyalty over diversified hierarchies.

Long-Term Impact on Chicago's Underworld Dynamics

The rapid succession of assassinations targeting the Genna brothers following Angelo's death on May 25, 1925, precipitated the collapse of their independent operations in Chicago's , enabling the to absorb their extensive bootlegging distilleries and distribution networks. Mike Genna was killed on June 13, 1925, during a with police, and Antonio Genna fell to gunfire on July 8, 1925, leaving the surviving brothers—Jim, Sam, and Pete—to flee the city and effectively disband the family's core structure. This dispersal fragmented Sicilian gang resistance in the Near West Side, shifting territorial control toward Al Capone's Outfit, which capitalized on the void by integrating former Genna suppliers and enforcers into its hierarchy. Over the ensuing years, the Outfit's consolidation curtailed the autonomy of ethnic-based rackets, particularly among , fostering a more unified syndicate model that prioritized profit-sharing over factional wars. The Genna downfall exemplified a broader transition in Chicago's underworld from decentralized, immigrant-led crews—often volatile due to blood feuds and Unione Siciliana disputes—to the Outfit's centralized command, which by 1927 under Capone enforced truces and expanded into and , reducing overt Sicilian challenges until the late . This realignment minimized intra-Italian violence while amplifying Outfit dominance, influencing the syndicate's resilience through federal crackdowns in the 1930s. By the mid-1930s, remnants of Genna influence had dissipated, with the Outfit under successors like maintaining hegemony over former Genna territories, underscoring how the 1925 losses entrenched a durable, non-ethnic power monopoly in .

References

  1. http://mob-who.blogspot.com/2011/04/genna-angelo-1898-1925.html
  2. https://graveyards.com/IL/Cook/mtcarmel/genna.html
  3. https://nationalcrimesyndicate.com/chicago-the-terrible-genna-brothers/
  4. http://chicagology.com/notorious-chicago/gangland5/
  5. https://www.myalcaponemuseum.com/id161.htm
  6. https://www.findagrave.com/memorial/3393/angelo-genna
  7. https://ancestors.familysearch.org/en/LTT8-Z5L/angelo-genna-1895-1925
  8. https://www.geni.com/people/Angelo-Genna/6000000163742196867
  9. http://chicagocrimescenes.blogspot.com/2009/03/terrible-genna-headquarters.html
  10. http://chicagocrimescenes.blogspot.com/2009/06/angelo-gennas-violent-life-and-death.html
  11. https://laborers.tripod.com/laborersorg/Genesis.html
  12. http://chicagocrimescenes.blogspot.com/2009/10/tony-dandrea-assassinated.html
  13. https://prohibition.themobmuseum.org/the-history/the-prohibition-underworld/bootleggers-and-bathtub-gin/
  14. https://austrianstudentconference.com/wp-content/uploads/2023/02/ASSC-2023-Sebastian-Anastasi.pdf
  15. https://www.chicagotribune.com/1997/08/26/the-genna-brothers/
  16. https://www.cemeteryguide.com/genna.html
  17. http://www.onewal.com/w-genna.html
  18. http://www.crimemagazine.com/part-ii-chicagos-unione-siciliana-1920-decade-slaughter
  19. http://www.crimemagazine.com/chicagos-unione-siciliana-1920-%25E2%2580%2593-decade-slaughter-part-one
  20. https://allanrmay.com/unione-siciliana
  21. http://www.crimemagazine.com/part-iii-chicagos-unione-siciliana-1920-%25E2%2580%2593-decade-slaughter
  22. https://www.wttw.com/chicago-stories/al-capones-bloody-business/beer-wars-and-al-capones-bloody-business
  23. https://themobmuseum.org/notable_names/dean-obanion/
  24. https://historycollection.com/live-die-chicago-7-famous-gangsters-met-violent-end-windy-city/3/
  25. https://mysteriouschicago.com/a-forgotten-gang-the-genna-brothers-part-1/
  26. https://themobmuseum.org/blog/friday-feb-14-the-st-valentines-day-massacre-what-happened-before-that-caused-this-infamous-crime/
  27. https://www.nytimes.com/1925/07/09/archives/3d-genna-gunman-slain-in-chicago-latest-victim-of-bootlegging-feud.html
  28. https://illinois.universitypressscholarship.com/view/10.5406/illinois/9780252037306.001.0001/upso-9780252037306-chapter-005
  29. https://historycollection.com/live-die-chicago-7-famous-gangsters-met-violent-end-windy-city/
  30. https://ancestors.familysearch.org/en/KHWH-S2Q/lucia-spingola-1903-1969
  31. https://www.findagrave.com/memorial/188676445/lucille-spiziri
  32. https://www.facebook.com/TimothyDMurphyIrishMafia/posts/the-genna-brothers-dubbed-in-the-newspapers-as-the-terrible-gennas-the-gennas-we/910963715688999/
  33. https://www.geni.com/people/Lucille-Genna/6000000163742256833
  34. https://homicide.northwestern.edu/database/7786/
  35. http://www.writersofwrongs.com/2017/05/chicagos-genna-is-laid-to-rest.html
  36. https://www.facebook.com/authortt/posts/the-end-of-the-terrible-gennasthe-genna-brothers-of-chicagos-little-italy-neighb/996192795206874/
  37. https://chicagology.com/notorious-chicago/gangland5/
  38. http://chicagocrimescenes.blogspot.com/2009/08/death-in-barbers-chair-rise-and-fall-of.html
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