Shaking Hands Can Be Unhealthy

By 1925 the six Genna brothers, or "The Terrible Gennas" as they were known ran the illicit activities in Chicago's Little Italy. practically the whole neighborhood was on the Genna's payroll cooking alcohol. The Genna empire began to fall in spring of that year when, depending on who tells the story, either Al Capone or the North Side gang struck out at them.

The first to go was brother Angelo that spring, followed by brother Mike, both of whom were the muscle of the family. On July 8, 1925,  brother Anthony aka Tony the Gent, received a phone call from a former associate named Joseph Nerone, alias Anthony Spano, known in the underworld as Il Cavaliere because of his polished demeanor. Feeling that the Genna's didn't pay him his worth, Nerone had moved on to Chicago Heights, and a more lucrative bootlegging career.

Nerone asked to meet Genna at the corner of Grand Avenue and Curtis Street.  Genna arrived first and waited. A sedan pulled up and Nerone alighted. Genna went up to greet him. As the men shook hands, two men walked up and fired a number of shots into Genna's back before running off. Nerone too, fled the seen.

We know that Nerone set up Genna because Tony the Gent didn't die right away. Later at the hospital, he was overheard telling his brother Sam that the Cavaliere was behind the murder. 

With the death of Tony, the Genna family was all but through in the Chicago underworld.

Tony the Gent Genna

End of a Flower Power

Chicago. November 10, 1924 -

Dean O'Banion, head of the North Side gang stands in the rear of his floral shop clipping chrysanthemums. He has received many orders from gangland associates for the funeral of Mike Merlo, the head of the Unione Siciliana, the man whom had been keeping him alive for a number of months. Both John Torrio and the Genna Brothers wanted him dead, but Merlo was able to keep them in line.

Earlier that year, O'Banion found out that a brewery he was part owner of was going to be raided. He saw this as an opportunity to make money and possibly get rid of a rival. He went to John Torrio and told him that he wanted out of the rackets and offered to sell his share in the brewery to the Italian gang leader. Torrio accepted the offer and paid the money. After the deal was made and the money delivered. The raid took place, resulting in the brewery being closed and Torrio facing jail time as a second offender.

Not wanting to start a war, it was decided that O'Banion wouldn't be killed. A few months later Angelo Genna ran up a large debt at a gambling parlor jointly owned by O'Banion and Torrio/Capone. The latter two decided to forget the debt out of professional courtesy. Afterwards O'Banion got on the phone and demanded payment.

Mike Merlo, whom Italian revered preached peace, but on November 8, he died. It was then decided that O'Banion would go with him. Since all of gangland used O'Banion's shop for their funeral arrangements he wouldn't be suspicious of unknown Italian men coming into his shop.

Around noon, three men stepped into the shop. Gangland lore dictates that the man in the middle is New York mob boss Frankie Yale. The guys on either side Genna gunmen Albert Anselmi and John Scalise. Hearing the arrival O'Banion walked out from the rear room. With shears in one hand O'Banion extended his free hand to the middle man. "Hello boys. You from Mike Merlo?"
"Yes." the man replied grasping his hand and holding it. As the middle man held tightly to O'Banion's hand the two side men each drew a gun and fired into the Irish gangster five or six times. O'Banion fell back onto the floor and another bullet was sent into his brain.

The killers fled the shop as the porter ran from the rear and found his boss in a bloody heap with his hands twitching.

 Dean O'Banion