Ragen’s Colts were a street gang which dominated the Chicago underworld during the early twentieth century. Made up of mainly Irish gangsters but there were also Italian, Polish and Jewish gangsters in their ranks. By the late 1920s and early ’30s, the gang became part of the Chicago Outfit under Al Capone.
Ragen’s Colts were originally established as an athletic club, Ragen’s Athletic and Benevolent Association, that was led by the team pitcher Frank Ragen. Members of the club were hired out to Chicago Democrat politicians to do various forms of election fraud during election days. Due to the gang’s activities and increased votes by an influx of immigrants from Europe, the Democratic Party gained control over the Chicago City Council and Illinois legislature.
The gang quickly grew in membership, in 1902 they numbered 160 members and grew to 2,000 by 1908. They earned the motto “Hit Me and You Hit 2,000”. By the end of the 1910’s, the gang’s influence and power had grown to such an extent that it had financed the careers of many of Chicago city officials, including aldermen, police chiefs, and city treasurers, as well as Ragen himself, Ragen would become a Chicago city commissioner.
By 1920, members of the gang had become notorious criminals and gunmen, such as William “Gunner” McPadden, Harry Madigan, Joseph “Dynamite” Brooks, Danny McFall, Hughey “Stubby” McGovern, Davy “Yiddles” Miller, and Ralph Sheldon.
During Prohibition, the gang like many others soon began bootlegging. One of its members, Ralph Sheldon broke away from the gang formed his own group and soon began hijacking rival liquor shipments. While the gang came into conflict with the Chicago Outfit during the bootleg wars, Capone, impressed with the gang, hired them as enforcers for the organization.
One of the gang members Harry Madigan owned a bar in Cicero, Chicago, right in Capone’s territory. Harry Madigan later explained to Chief of Detectives Schoemaker how matters had stood: ‘When I wanted to start a saloon in Cicero more than a year ago, Capone wouldn’t let me. I finally obtained strong political pressure and was able to open. Then Capone came to me and said I would have to buy his beer, so I did. A few months ago Doherty and Myles O’Donnell came to me and said they could sell me better beer than Capone beer, which was then needled. They did and it cost fifty dollars a barrel, where Capone charged me sixty. I changed, and upon my recommendation so did several other Cicero saloonkeepers.'” This would lead to more bllodshed between the Chicago Outfit led by Capone & the O’Donnell’s led by Myles & his brother William “Klondike” O’Donnell.
However, there would be a shooting outside of the Pony Inn that would shock the most battle weary in Chicago, the shooting of Assistant States Attorney William McSwiggin who was shot to death on the steps of the bar. According to ChiTownView’s Channel on YouTube:
“Assistant States Attorney William McSwiggin had two sides to him and it ended up costing him his life. By day he was known as a hanging prosecutor who tried to bring Al Capone to justice. By night he was a card player, drinker and all around bon vivant who traveled in the same social settings as the men he prosecuted. It was late spring in 1926 when he was out for a night of carousing in Cicero with some friends. Along the way the hooked up with the O’Donnell brothers who were well known north side gangsters who were at odds with Al Capone. Al Capone got word that his enemies were out and about in his town he dispatched gunmen to take them out. They caught up with the group at the Pony Inn on Roosevelt Rd. just west of Central. The Pony was a Capone controlled speakeasy that was run by an Irish mobster named Harry Madigan. Madigan was a member of the renowned Irish gang Ragen’s Colts. He would later go to jail for kidnapping and extortion. Anyway the gunmen raked the group with machine gun fire as they left the club. Three were killed including McSwiggin the O’Donnell brothers escaped unscathed.”
In another shooting, two members of Ragen’s Colts were shot to death at the famous Granada Cafe, Hugh “Stubby” McGovern & William “Gunner” McPadden, were both shot by a relative newcomer to gangland George Maloney. Police said they rushed into the cafe upon hearing the shots and found Maloney with a gun in his hand, they initially believed that the shooting was in connection to the Beer Wars but came to the conclusion that it was connected to the division of loot between the gangsters.
The Ragen gang were eventually absorbed into the organization following the establishment of the National Crime Syndicate in 1932. Many members would later become top leaders of the Chicago crime syndicate.
In 1920 several members of Ragen’s Colts split off to form the NFL football team, the Chicago Maroons, later known as the Chicago Cardinals.
Carl Sifakis The Encyclopedia of American Crime.