As I see it, a lot of the pictures taken featured a CW watch, with a summery, but somewhat out of focus background. Had I seen any sun in August I am sure mine would have been a similar idea.
So maybe CW were looking for something rather different, and maybe there weren't many entries featuring a CW in an action shot.
That picture must have needed both a model and a photographer, or maybe the camera was on a tripod, and able to capture a series of shots, and the photographer then picked one of the series.
I can see why the reaction might be a bit "meh", but it was actually quite a tricky brief for a single photo, I think. I would have preferred to see a larger watch, but it's hard to do large watch AND summer.
I like the super compressor picture that
@rkovars took, as everything is in focus, but it doesn't scream summer so much. Is it a fishing rod in the background?