John Wick has pissed off a lot of people in his two theatrical appearances so far, but he isn't without allies. Ian McShane's Winston has been arguably John's biggest supporter, and while Laurence Fishburne's Bowery King interest in John during John Wick: Chapter 2 was more self-serving, he nonetheless helped the hitman when no one else would. Both men will be back next year in John Wick 3: Parabellum, and the latest image from the production shows Winston and The Bowery King finally coming face-to-face.
Given their respective positions within this world's assassin community, it's guaranteed Winston and The Bowery King are familiar with one another, and perhaps they've met before the events of the John Wick movies. However, both men interacted with Keanu Reeves' John separately during John Wick: Chapter 2, so it'll be in John Wick 3: Parabellum that we see them meeting onscreen for the first time. Both men are very powerful within this community of killers and colorful criminals, Winston being the manager of the Continental Hotel's New York branch and The Bowery King being an underground crime lord commanding an army of homeless agents. Seeing them together, I can only imagine what they're meeting about in this picture, though it's a good bet it involves everyone's favorite badass assassin.
As far as their relationships with John Wick go, Winston definitely cares more of John's well being than The Bowery King. Granted, Winston was forced to tell John at the end of John Wick: Chapter 2 that he'd been declared excommunicado by the High Table for killing Santino D'Antonio on Continental grounds, as well as call in that the bounty on John's head had been doubled and offered globally. However, Winston gave John a one hour head start and a Marker for future use, so clearly he has a soft spot for John. The Bowery King, on the other hand, only helped John in Chapter 2 because if Santino gained more power, his operation would eventually be kaput. So while Winston will hopefully still be supportive of John in John Wick 3: Parabellum, there's no guarantee The Bowery King will follow suit.
Along with Winston and The Bowery King, John Wick 3: Parabellum's return characters include Lance Reddick's Charon, Ruby Rose's Ares and Common's Cassian. The threequel's new players include Halle Berry's Sofia, Angelica Huston's The Director, Asia Kate Dillon's The Adjudicator, Mark Dacascos' Zero and Jason Mantzoukas' Tick Tock Man. Parabellum will see John trying escape from New York, fighting and killing anyone who stands in his way.