This is an old question, but I recently wandered around it trying to solve the same problem ...
According to the documentation :
Elasticsearch supports sorting by arrays or multi-valued fields. mode determines which value of the array is selected for sorting the document belongs.
So you should be able to sort like this:
"sort" : [ {"usernamesAssigned" : {"order" : "asc", "mode" : "min"}} ]
It is available from version 0.90.0.Beta1.
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