Sewer Socialism in Milwaukee! Okay more to it than that, and I may need someone else to jump in and fill some of the gaps, but it all centers in Milwaukee being a city that had a strong socialist party. We've had multiple mayors who were openly socialists, and even have a bridge named after one of them! But you probably already know this, or at least part of it. The reason for this strong socialist leaning is due to immigration. Milwaukee was basically a German colony on the shores of Lake Michigan. Obviously that's a bit of an exaggeration, but during the 19th and early 20th centuries we see a huge number of German speakers move to the area. I use German speakers as opposed to Germans as many were from other European nations but were still culturally "German". I can personally attest to this as well, my own great grandfather was born to immigrants from Hungary/Romania in the early 20th century. He grew up speaking German at home and English everywhere else. Through genealogy I have also found his various family members belonging to various German clubs and organizations in Milwaukee. I apologize as that is anecdotal, but I hope it shows just how German Milwaukee really was. They even called it the German Athens, which gets at it being a center for not only German culture, but also for German thought/debate as well.
So how does this relate to socialism? Well from the 1840s on, much of Europe was dealing with revolutions. I am not even remotely close to an expert on this, but from what I have read a lot of it was a blend of democratic/socialist ideals. Between fleeing failed revolutions and wanting to avoid it all together, many immigrated to the US. These people brought with them many of the modern political views that were taking hold in Europe. As the decades progressed, this meant that many brought over socialist ideas as it too took hold in parts of Europe. Milwaukee has a strong history of being a very liberal city, so it is no surprise that many of these ideas were quick to gain support here.
This doesn't really explain why socialism stuck though, I mean how can you have a socialist city in the same state that also created the Republican party. That's a bit of an unfair statement as those terms have changed a lot since then, but even today Milwaukee is far more liberal than most of Wisconsin. This is where sewer Socialism comes into play. It was a term that came about in the 30s to sort of poke fun at Milwaukee socialist as they were quite proud of the world class sewer system that had been constructed in Milwaukee. Jokes aside, this is why socialism was so popular in Milwaukee, because it worked. People in Milwaukee were fighting for an 8 hour workday from the 1860s onward and it represents just how committed many in the city were to pushing socialist ideals to benefit the working man. One of the socialist mayors, Hoan, helped to establish the park system that still exists today in Milwaukee. Hoan also helped to establish the first municipality sponsored public housing progress in the country. There is a reason we named a bridge after him!
Tldr: the history of Milwaukee is the history of socialism in Wisconsin. It's unique to our great city and resulted in socialist mayors and representatives being elected to represent the citizens of Milwaukee. Immigrants brought over new ideas and a culture that promoted ideological debate. This planted the seeds for socialist leanings in Milwaukee, and which when given the chance, grew into a strong socialist movement in the early 1900s due to it's ability to help the workers of Milwaukee.