It Works!!!!
Here's what i did to make the trophy pop:
First, You MUST Resign all 3 saves to your USB Drive
Next, DO NOT Resign the Profile data at the bottom of the file
Next, Add the save to your PS4 & Load up the game
If Done Correctly it should have you continue the story from the final checkpoint of the very last mission " The Death of Art "
Kill Sam & skip the cutscene & the Made Man Trophy will pop !