Editor's Note: Bill Matteson's story about bootlegging brought back some memories for this reader. We saw his story in the comments, and felt it deserved its own post. Thanks for a great story, Al!
When I was about 17 or 18 years old some friends and I were going to head up north to Ardmore Beach for a party and thought we'd pick up some booze first and in order to do that we had to find someone to buy it for us, which usually meant finding a bum to do the purchasing.
We decided the best tavern to stand out in front of was this basement dive called the Hide-a-Way on the south side of Montrose, just east of Hazel. After about ten minutes, this guy comes stumbling out and the first thing he says when he sees us is "stay away from me, cuz I ain't got no money and I'm dangerous." I told the guy we didn't want to roll him, all we wanted was for him to buy us some stuff and we'd be willing to buy him a bottle for himself. That he said would be no problem since we were buying. We gave him our money and order which we kept simple considering his condition.
It was the usual stuff teenagers got at the time: Boonesfarm, Ritchards, Wild Irish Rose, and some half pints. So he went back inside and we waited and waited, it took him about a half an hour to come back out with our stuff. We asked him what took so long, and he said the guy wouldn't sell it to him because he knew it was for those kids outside and it took him that long to talk him into it. We knew he was giving a line and figured he got a couple of shots on our money and there was nothing we could about it, so we went on our way.
When we got to Ardmore and passed the stuff out, I could'nt believe what I saw and realized why it took so long to get our stuff. He had opened up and drank just a little bit from each bottle.
Its over 40 years since that happened and I'm still friends with those guys. Whenever we get together and if we are talking about the Uptown days it seems like only yesterday that we were eating burgers at Jake's Pup in the Ruff before going to a Cubs game or the Uptown Theater.