lol...in all honesty...i know the shield wouldn't get mangled like that when hitting Supes....but it would be cool if it did....it would make a lot of guys shit in their tights..lol
He might be able to, as might any of a number of other high-level strongmen/women from both DC and Marvel...but since that feat has never actually been recorded by anyone, we'll never know, will we?
Besides, the shield would likely not crush on mere impact with Superman's chest...it'd have to be some willful attempt to crush it...