Tooker Alley Chicago



Original Painting - Acrylic on canvas 20x16

One can almost imagine the denizens of early 20th century Chicago climbing over the garbage cans “down Tooker Alley to the Green Light over the Orange Door” to get to the famed Dil Pickle Club.

The club was almost hidden from the outside and was considered a "hole in the wall" in Tooker Alley. The entrance was marked by a "DANGER" sign that pointed to the orange main door which was lit by a green light. On the door, it read: “Step High, Stoop Low and Leave Your Dignity Outside.”

During the Great Depression, the Dil Pickle Club began to experience its decline. By the early 1930s, the club was being frequented more by Chicago mobsters rather than the usual free-minded Bohemian attendees of the earlier era.

Machine Gun Madam

Original Painting - Acrylic on canvas 16x12

“The voluptuous blonde bombshell just delivered a Chicago Valentine to a couple of wise guys trying to muscle in on her operation ...a hooker with a heart of hot lead instead of gold.”

I had a lot of fun painting this and learned a lot about the Thompson Submachine gun; also known as, the Chicago piano, the Chicago typewriter, Chicago Organ Grinder, and the Tommy Gun.

Gangsters and Bootleggers of the Prohibition and Depression era made this their weapon of choice. It has been referred to by one researcher as the "gun that made the twenties roar." The Thompson Model 1928 submachine gun came with a 20 or 50-round drum magazine and a .45 caliber punch.

This was the weapon used in the infamous Chicago St Valentine’s Day massacre where seven members of the North Side Irish Bugs Moran gang were mowed down by Al Capone’s South Side Italian gang.