Yep,
he left his jacket and cash behind... but that was AFTER he took the watch.
You need to remember he has lived by a 24 clock for his daily meds for years and he was starting to lose his focus when they entered the facility. He may not have been entirely sure why he did it at the time - i considered it an instinctive decision from a guy who had come to fundamentally depend on his watch, so I wasn't looking at it from a purely logical point of view.
But I also agree with the logic - wearing a $5,000 watch is like wearing a money belt, and they used it to compensate the boat owner for escape and safe passage in the end so it was shown to be a smart move. But that was his happy ending - he no longer needed it because he no longer needed the meds... he was finally free. The watch was a symbol.
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