This discussion may contain spoilers!
Remember how in TWDS1, when you finally caught up with the Stranger, he sat you down and had a talk about all the things you did that season. I think The Crooked Man may fill this role. In the screenshots and the trailer, Crooky is holding Mary's gun at Bigby. I think this very well may be where he forces Bigby to think about all he's done over the course of that Season. If not there, it could be at the start of the episode in his lair. What do you guys think? Will there be a "judge", and if so, will it be Crooky? What actions do you think he'd judge you on throughout your playthrough? There could be the mistreatment of Dee/Woody, killing Dum, burning down Greenleaf's tree, etc etc.