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It's not like filling in the empty dates of ancestors is the end all be all of genealogy, Roy and I both agree that it's the mundane stories of how people lived that are sometimes the most fascinating, but getting back to the 14th century is pretty cool.
In this case, the Watkins are related to this guy by Catherine Anwyl, wife of Watkin Roberts. (His complete pedigree is in Griffiths' Peds of Anglesey & Carnarvonshire Families.) The other interesting thing (and you can't make it out in this picture) is that his shield is the same family crest/heraldry that was on Robert Watkins' legal documents.