when i worked line i was pulling a 182 with wheel pans. i had just washed it and was pulling it across the ramp with "Lecktro"...those lobsters that push back RJs...since i was going backwards i also happened to be looking that way...i turned around and the airplane was no longer attached...uh oh...it was rolling towards me though...before i could move, it ran up on the tray and shattered the wheel pan! the reason i was washing it was because it just came out of annual and had new wheel pans put on and was going to a pre-buy the next day!
another time i managed to tow a bonaza across the field with its parking brake on. overheated the tug and warped the brakes on bonanza.
what has made me a legend however is an incident with a golf cart. well the long and short of it is that it didn't have very good brakes. it was my second week at my new line job and i managed to crash through the side of the hangar...i was mortified thinking that i just threw away my aviation career...even the FBO owner couldn't stop laughing...