It means you live near idiots. Just like when you find any other evidence of idiots: empty beer bottles, plastic bags, fast food wrappers or squirrel posion. Rogers Park is full of inconsiderate idiots who don't care what the neighborhood looks like, much like much of the city.
I think if you let the alderman know they will cut the shoes down.
or some poor sap just happened across the wrong group of jerks. When I was a kid (in this neighborhood) oftentimes a bully would toss a pair of shoes over a phone wire just to be a jerk after picking on some poor kid.
Other possibilities; (1)One shoe wont stay up there alone without the other (2)Someone was hung there upside down and fell. (3)Someone thought by doing this, it would drive people crazy wondering why..
Whenever my husband and I find shoes hanging in our neighborhood or in the park nearby, we cut them down ourselves if possible. If they re-appear, we cut them again. After removing them two to three times, the dealers/gangsters/wannabees usually get the hint that they shouldn't be putting shoes in that area anymore. Some may say this is risky, but we have never been confronted by anyone while removing the shoes, except for a neighbor who thanked us. I think the shoe pushers move on to an easier, less watched out for area to do their deeds once they see their shoes are gone a few times.
As someone who stares at shoes on his wires, I can tell you that's it's not about open-air drug markets or gang territory. Mostly I think it's just kids tossing shoes into the air, because it seems like fun.
Whether or not it's just some kids having fun or it is a signal for some gang-idiots, it makes a neighborhood look ugly. The neighborhood looks much better without dirty sneakers hanging from wires or tree branches.