WIsconsin has had its fair share of OC activity over the years. Milwaukee is only 80 miles North of Chicago. Italians from Chicago have vacationed, moved, set up shop, etc. all the way north to the Upper Penninsula of Michigan. Capone owned lots of land all throughout Wisconsin. There is a resort/golf course/getaway up there that he frequented, that still has pictures on the wall of Al with Prio and Nuccio. I think "Nags", "Libby", and "Bell"(3 Doms) are in a pic also.

My mother's family was based in this area(Green Bay/Appleton) and she took off to Chicago(School Street/Grand Ave./Elmwood/Harwood Heights) as a teen in the 70's, where she met my father. My mother and father are both of Sicilian descent. I have great great grandparents that emigrated and settled in the Upper Peninsula of Michigan also. My Chicago family vacationed throughout Wisco and Upper Michigan heavily during the 50's through the 80's. I recently ran across a memoir by someone of the Lucchese surname who settled in the Copper Harbor of Upper Michigan around the 1900's. Wish I had picked it up. My Chicago G.P's tell me I'd be surprised if I knew how much the Upper Peninsula resembled Sicily.

During the the early part of the 1900's lots of Prohibition outlaws hid out or got away in those parts. I can't really say too much about the NYC/Wisco connection, but if anyone from NY that rubbed elbows with Outfit, I am sure they probably saw some of the scenery. Wisconson has a "Gangland Tour". Not sure where all it goes or what it does, but you could research it and see what they say. Not sure if this answers any of your questions or is even helpful, but I figured I'd throw some info out there.