Some pair of osiris circa the storm era. They had a solid rubber bit at the front of the toes - but the rest of the upper was soft. Every time i landed the rubber bit would snag perfectly between my big toe and toenail and wrench the toenail off a little more. I was poor, they were new, i tried everything i could to stop it happening but the agony continued until they pretty quickly got binned. Ive had badly designed shoes, shoes that blew out quickly (ipaths on both counts) but no other shoe has caused pain akin to chinese torture methods so they win. On the flip side ive had shoes that have been almost too good - gotten so bored of them (its always the plain ones) yet they soldiered on and i couldnt justify binning them..