Мафия 4. The Smell of Money.

It's all too confusing for me. I think Amaranth was checking on Kyle's status, but he was killed by one of the factions. The clues are probably these:

...causing terrible pain and suffering...

Cadillac doesn't seem to be connected to Arandor, Tengro, or Nick. Maybe I just can't make the connection – I don't feel like thinking about it :) Maybe it's only connected to Vistrit, since he's a black dragon.
As for the .44 caliber, we need to dig deeper, look for links, hints, etc. in the profiles, and study them. I'm already starting to lose motivation).