I know, they have so much sentimental value! You ran from the cops in them, that one night you were at TJ's house, and you got away! (TJ wasn't so lucky.) And maybe if you just put them through the wash — like, two or three times — and found a good cobbler, you could save them, right?
Wrong. There are many more shoes in the world and your feet will thank you for it. Toss that ish NOW. (And if you want to get rid of shoes that are in more serviceable condition, donate them to an organization like Soles4Souls.)