I think he might be a New Year card.
In keeping with the fun so far, this was loosely drawn after a wood cut in History Today magazine. Apparently he's carrying the news of a great victory to do with the Hanseatic League. That's Stockholm in the background next to the ship, can't you tell?
Either way, the original was stiff like this, and coloured and rather oddly fun. Strange cramped proportions (look how small that horse is!)
I started it in thin drawing/marker pen, but it just didn't look right so I went to town with the biggest pen-nib I had and lots of splashy India ink. That's better!
I'm thinking he'd look pretty good screenprinted onto a messenger bag (ho, ho).