Al Winter

The Desert Room nightclub (today’s Hal’s Café) had an underground gambling den that kept club owner, Al Winter, on the FBI watch list as a so-called “Top Hoodlum.” Al owned shares in a string of nightclubs in Las Vegas and was linked to some notorious underworld gangsters of the day. (Al’s Den, the Crystal Hotel’s basement music venue, is named for him.) 
Artist Lyle Hehn was inspired by the 1934 film, Freaks, and its famous scene of carnival people sitting in front of a circus wagon. Regarding his painted portrayal of Portland’s gangsters, Lyle explains: “The thing about the history of these guys is that they were not nice people. And I didn’t want to do a painting of them that embellished their memory somehow. I wanted to put in a little bit of my opinion of gangsters.”