I believe there have been several such cases.

I know of one individual who taxied into the back of another aircraft and in a separate incident taxied into a clubhouse while uninsured. Being a handy sort of chap, he repaired both the chewed up rudder and the clubhouse (and his own aircraft) himself. He had a tailwheel aircraft with no park brake and limited forward view.

These are at the lower end of the accident scale, but there have been other more serious incidents.

In the US their is no legal requirement to be insured, but most airports won’t accept you as a based aircraft without insurance.