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That check isn't related to Kade - it's about sleuthing and successfully finding the murder weapon. (trying investigating the servant's quarters after you've figured out what the real cause of death is) Hope that helps <3

Oh I know, but I just mean that I *did* do the investigation correctly. I've played the whole game a few times already with no issues and just doing the same as always, but it wasn't showing up this time playing as a Pirate. I started another Widow play through last night, did the same and got the option to choose Lee though. That's why I was mainly wondering if it was maybe a background only bug? 

Though maybe I did miss something by accident that playthrough? I'll check for Pirate again and edit this comment later. Anyway, thanks for responding. <3

nope, backgrounds aren’t checked there at all, just clues <3

I didn't mean that I was thinking that there was a background check either, just that the clue check to be able to choose Lee after a perfect investigation wasn't firing on the Pirate background specifically. My bad for not being clear enough.