Don't Bet on the Ponies

It was a bookies war, or so the Chicago police believed, that claimed the life of John "Irish" McLeod and the wounding of his partner James Ryan. McLeod was a former employee of Moe Annenberg who published the Daily Racing Form and was sent to prison the previous April.

McLeod and Ryan belonged to a group of independent bookies operating out of Chicago's South Side. Their group may have been planning to publish a racing service paper to fill the void left by Annenberg's removal. This put them at odds with other gangsters who had the same idea. Namely, former Prohibition gang Leader, Danny Stanton.

Two of Stanton's boys, Michael McGovern and James McGlade were bumped off the previous June. Police say the were searching for James Ryan but he managed to elude them, that is until July 26, 1940.

McLeod and Ryan had just exited an A&P grocery were store with a stock of can goods. It was believed that they were planning on leaving town as they knew they were on the spot. Just as they got into McLeod's car, a sedan pulled up and three masked men, each armed with sawed off shotguns, opened fire on the duo. McLeod lost a portion of his head and was killed. Ryan caught some of the shot, and although seriously wounded, survived the hit.

John McLeod       James Ryan

Chicago Ride Job

In the early hours of July 15, 1931, Milton Winfield sat in his Chicago home. He heard a series of shots and ran to the window. Looking out, he saw two men jump from a sedan and the driver slumped over the wheel.

Another sedan pulled up and a guy climbed out, went over, and pushed the slumped body of the driver off to the side. Perhaps he was just making sure of the job. The men then drove away.

The police were summoned and the dead man turned out to be Edgar Smith, body guard of Al Capone confederate Danny Stanton. Both Smith and Stanton had been arrested the previous year when ballistic test proved that a gun found in their car was used in the murder of Jack Zuta.

At the time of Smith's murder, Stanton was at war with another South Side of Chicago gang headed by James Quigley. It was also hypothesized that friends of Zuta pumped the three bullets into the back of Smith's head.

Edgar Smith