Really? I don't know what kind of criteria they use to choose, and I'm not saying I'm an expert art critic, but to my eyes the winning entry is fugly, uninteresting and unoriginal. I mean it looks like it was drawn with crayons ffs.
The 2nd one (the antarctica one) looks better designed, but again the style is unoriginal.
The 3rd one (seattle) looks nice, with a nice style, but there's absolutely no aspect of the image that says "map" to me.
What really hit my eye was that none
of the prized entries were actual maps.
One would think that a mapmaking contest would reward at least one entry that was a map