I have the following XAML:
Per the MSDN documentation...
ContextMenu itself is a FrameworkElement derived class, but the ContextMenuClosing event will not be raised by a context menu directly. Instead, the event is raised from the element that "owns" the context menu as a property and is only raised when a user attempts to close a context menu in the UI.
You would need to adjust your code so that the handler is defined solely on the DropDownButton as you have done. If there is a nested ContextMenu then the nested ContextMenu will obviously raise the event.
...
Using a Button it would look like this...
..where when the ContextMenu containing the MenuItem closes; the event will be raised and the handler will be called.
Not certain what DropDownButton control you are using so I can't comment on what the DropDown property is and how you are nesting your ContextMenu.