So now that I know that the the cityscape in the drawing of Emirikol the Chaotic was taken from the Street of Knights in Rhodes; I fired up Google Earth and the photo feature to see where the guy was heading.
In the picture in the right the red line represents the Street of Knights and the supposed path of Emirikol the Chaotic.
The crude X is roughly where the viewpoint of Trampier's picture is located.
A short distance behind the viewer of the ride is a small enclosed plaza ( I am sure there some technical term for it). It has a roof and archway all around it from what I can tell. It looks large so I don't think that would be a problem.
Until he stopped death raying his pursuers and turned around.
Looks like he riding right into the courtyard in front of the main castle. If he lucky (and skilled enough) he may be able to get out by a road going to the right of the enclosed plaza but given the breakneck speed suggested by the drawing and the fact he just 10 feet or so from entering said plaza that probably unlikely.
So into the main courtyard where the guards undoubtedly wait. If was in the Majestic Wilderlands they would have Knight Killer Crossbows as well.
Well Emirikol it was nice knowing you.
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