In the lead-up to and during Winston’s meeting with his Uncle Charlie, it’s revealed that both he and his brother, Frankie, refer to him as Captain Reliable. It’s certainly a fitting title given how much he lends a hand to the future owner of The Continental, giving him his car, a black Mustang (which is a nod on wheels to John’s signature ride). It also makes sense that whatever happens between the end of the events of “The Continental” and “John Wick,” he redirected his focus to the disposal of evidence in its various bloody forms.
If there are any further trips to the timeline that fill the gap between now and John’s mission of vengeance, it’d be great to see Charlie eventually change his trajectory and give the old body disposal business a go. We know he cleans up pretty well for the right price and, as his nephews can attest, will provide a reliable service in all the years to come.