Hey, we all talked about how this episode was like so many of our favorite Broken!Jack future fics, so here's a few off the top of my head. (And given my reading preferences, these are all Jack/Sawyer.)
zelda_zee's Aurora Borealis series, for one, with the premise that Jack took the deal Ben offered him and got off the island.
eponine119's Test Drive, with a suicidal Jack.
ETA: It was Perchance to Dream by eponine119. Go read now, but bring tissues!
LINK ME. I'm sure there are many others I can't think of right now! I
Oh, and because this one is so wonderful Future Broken!Sawyer. Writing Truth by eponine119
And FWIW, some comment pron I wrote with Jack stealing medical supplies ... and giving them to Dean Winchester in exchange for blowjobs! LOL.