Before crossing the event horizon, please remove your watch

In a life that is going wrong, when one stands at the margin, very often the last meaningful item in your possession is your watch.  It comes up again and again in moments where an individual is crossing over, leaving our sight for unknown realms.  The Greeks would place a coin in the mouth of the deceased, to give to Charon to cross the river Styx.  So maybe that's the way to think of it - a watch at the exit, a coin at the entrance.  In any case, oftentimes one's last act in extremis, is arranging for the disposition of the watch.

A field hospital at Gettysburg

As he lay mortally wounded, Confederate General Lewis Addison Armistead - the point man on Pickett's charge - made his final arrangements.  The Baltimore Sun reports that he sent regrets to his old friend Hancock, and gave instructions that his watch be conveyed to him on his passing.  

The Warsaw Ghetto

According to The Imperial War Museum,

In the summer of 1941, Willi Georg, a German Army signalman, visited the [Warsaw] ghetto on his commanding officer's order. A pre-war professional photographer, he took four rolls of films – around 160 images – during his one day visit to the ghetto.

Object description:  "A young man in the doorway of a shop in the ghetto. Note he has taken his hat off to comply with the German order to remove headwear in the presence of German personnel. The shop offers fresh eggs, sweets and watches. The sign in the window reads - "I buy old watches for top prices".

From The Holocaust Encyclopedia:

Stalingrad

I greatly admire the Facing Stalingrad project of Jochen Hellbeck at Rutgers, in which he tracked down soldiers from both sides who had been there and talked with them in 2010.  The timing was perfect.  These people were in their 80s and 90s, and most had maintained a principled silence about their experiences.  But at that stage of the game even the most stoic types tend to lose their filter a little bit, and even when the subject seemed initially reluctant, Hellbeck generally got an earful.  A good photographer accompanied him, and her work helps bring the conversations to life.

Johann Scheins was still pissed about losing his watch during the surrender:

[T]hen all of a sudden, at around 3:30 PM, two Komsomols came in, the Russian Hitler Youth... Two men. Chassy. Chassy – watches, watches, watches. Various things, various watches, various chassy. So every German took off his watch, and I took off my watch. My watch had a silver watchband. I placed it on the ground and laid my boots on top. That’s what I did. And one of the Russians saw that and beat me with his gun.

The Western Front

In All Quiet on the Western Front, young Kemmerich lays dying in the hospital in 1914, annoyed at the pain in his foot, which he does not know has been amputated, and concerned about his watch, which has gone missing.

It grows dark. Kemmerich's face changes colour, it lifts from the pillow and is so pale that it gleams. The mouth moves slightly. I draw near to him. He whispers: "If you find my watch, send it home--"