I've broken a bunch of stuff at Summit, but nothing "major"-- not that it stopped me from feeling like sh*t about each one... Worst was either sending a machine home with a boring bar in a part, which broke our last tool holder for a busy weekend, or grenading a brand new tapping head when I selected the wrong tool. But it could be a LOT worse at a machine shop. I think mine have been relatively small but pricey effups.
I totalled a cherry '72 Chevelle, looked like all original survivor-- by dropping a 40' tree branch on it being a hotshot. I had intended it to be super cool, I'd let it start coming down and just zip the little strap of tree I left, so it would fall on one side of a bigger branch below it, and then it would be so rad and fall into the park and the crowd would ooh and ahh... except that it landed just a little too vertically, and sprung back on the leafy end, and very, very slowly wobbled... and wobbled... and then I watched a 40' hammer swing with increasingly velocity at the C-pillar of that perfect Chevelle. I almost cried when it hit... and I had about 60' of boom to come down from with everyone watching silently. Then they cheered because I finally wrecked something, and told me all kinds of horror stories, about wrecking a 7-11... destroying the Midvale city sign in the median... etc etc. I felt pretty bad about destroying that classic old Chevy, but oddly enough, no owner was found, and no one ever submitted a claim against our insurance for it... weird.