Theory 1:
Winston is John Wick’s Father In Law.
Evidence:
We know John’s ex wife’s name was Helen. We know this because Winston says it in the first movie by Winston and this is the only time that her name is brought up in the series.
Winston gave John 1 hour to get away before declaring his life forfeit for conducting business on Continental Grounds.
Winston keeps helping John in ways that it doesn’t seem that he would help anyone else in that world. Winston has a bond with John that goes much deeper than friendship. It makes sense because John would have met his wife through Winston possibly at the Continental.
Theory 2:
Winston is making a play to destroy the High Table to become the only person at the table or at the very least the head of the table.
Evidence:
In the first or second movie, there is a guy with Winston outside of the Continental and Winston is inspecting the gold coins that fuels their world. Winston is looking at some of these very closely stating, “nearly perfect.” I believe that Winston is either creating his own currency for his rule OR he is trying to de-fraud the currency with counterfeit coins.
Winston is using John to wipe out the high table through his relationship with him which is why Winston didn’T kill him the two times he should have. Laurence Fishburne’s character is in on it now which is how they got the dog from the Continental at the end of the 3rd movie and was in the “King’s” thrown room when he sees John’s finger cut off. Winston and Fishburne’s character are possibly creating a new high table with Winston at the head.
Thoughts?