Leo is not new to being a vampire of the Red Court. He's not a noble or anything, but he's been around for a very long time. He's reached the ripe old age of 600, outliving his noble father and the vast majority of his bloodthirsty sisters, almost entirely by being a filthy coward. He has no pretensions to the blood of milk-pale virgins; he's perfectly fine getting his dinner for the week under a bridge. He occasionally keeps slaves, but only rarely. Most of the time, he occupies himself with reading, and painting, and delicious, delicious blood. On occasion he indulges in a good alleyway lurking.

This is one of those occasions. Chicago's alleyways are not particularly well maintained, but they're better than the slums of Toledo in 1632. Leo likes them. They're meditative, and often contain convenient homeless populations.