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Regarding WW I wristwatches, I've never heard of any officially issued to pilots. I have seen two private purchase trench watch style American wristwatches where the guys had some jeweler engrave their names and "ASSC" on the back. I have my doubts that the engraving was done at the time, though of course anything is possible. More likely it was done after the war as a rememberance, or even possibly very recently as a deception.
I've also seen a great many WW I trench watches being advertised by sellers as being pilot's watches and pointing out the large lugs that "must mean there was a very big strap attached that would have gone all the way around a heavy flying coat sleeve" or "the dial is very large and so must have been used by pilots" or "the number 12 is red while all the other numbers are black and that was the secret code for it being a pilot's watch or an officer's watch" and other such strange claims. I believe this is fanciful or hopeful selling at best, or perhaps just ignorance, but more likely deception to get a higher price for an ordinary trench watch. I'm sure many pilots had personally purchased wristwatches and pocket watches but there is no evidence that there would be any special brand or style they would have bought at the jewelers as opposed to what any other soldier would have bought for themselves.
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