That's what I thought - the moment he gave her to the Commodore, he sold his soul. And that's what killed him at the end. Awesome story overall. Going to miss it. Also, Nucky's death was depicted the same as Jimmy's. Both shot in the cheek, both dying with their defining moments (diving for gold, the trenches) replaying. Wow. I always found the Darmody family story so tragic.
Interesting, yes. But actively matching these things? That would be super contrived, even by Italian standards. Same for the watch strap, in my opinion at least. I think we'd see the patch pockets' lower outlines. I like that outfit/photo very much, though I personally would chose a white (casual) shirt.