Oh man i'm not even sure what I did to bug it out, I tried a new game and it is working fine now
Here is a save file of the playthrough where it won't drop though, dunno if that will help or not

Im getting Patrick beat up by either Frank or Madison but he holds onto the bottle of Merlot even when he is unconscious,
when talking to Patrick after he gets up he says he dropped the wine but it is still in his hands