JQL doesn't have the ability to "count" anything - you would have to grab that kind of data from the JIRA database.
You can specify a past assignee in JQL, which will show you if an issue was assigned to a particular user at some point:
assignee was "username" and issueKey is XXX-YYYY.
This would give me some of the information I am seeking, but it's not practical to implement. I appreciate the suggestion though.
I'll chalk this up as "currently not possible" using JQL.
I think there might be some plugins which do this sort of thing, but I can't justify the cost for this one purpose though.
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