The core code has not been edited for years. It looks like some of the implementations improperly defines the Describable generic., but I cannot pin point to the failing plugin. It is likely a plugin with a really old core dependency.
Somebody could add some diagnostics to the core. to track down failing descriptors in the rebuild() call. It could be logging on FIEST level or just runtime exception handler
I am coinverting it to the Core issue for better error handling and diagnostics. Whatever is the failing plugin, Jenkins should be robust against such issues.