This was a well-imagined and creative look at Gibb's possible past.

The explanation for why he turns to heavy drinking is very plausible. We just know he's often drunk, but it's interesting to stop and consider why.

'Anne kissed his blinked and she was gone'

I think your last line got muddled in editing or when you uploaded the story. (I hate that!) Double check it.

Already Gibbs has acquired a good story to tell -the time he met Jack Sparrow! I love the idea you had for their meeting. It would be just like Jack to nearly get himself tossed out, and I suspect funds were low if Jack was sticking to just one drink!

I liked that Anne appears once more to Joshamee, and convinces him to try to live life and gather good stories.

'“Jack Sparrow?”

“Yes. Watch him. He doesn’t have anyone. Not really, all those smiles…they’re hiding sadness, but he does love this life. You need to remember how. He’ll give you stories to tell. And I’ll want to hear them when we see each other next. You won’t forget?”

Gibbs shook his head, “Never.”'

This is really very touching.

Nice job looking at some of what makes Gibbs the pirate we know him as! :)

Cheers!
Nytd