Ian McShane's Winston has been a constant throughout the John Wick franchise. The character debuted alongside Keanu Reeves' eponymous assassin in 2014's John Wick, and Winston has appeared in every entry since, including the upcoming Ballerina spin-off film and Peacock's divisive prequel series, The Continental (played by Colin Woodell). John Wick 5 appears to be an increasingly strong possibility at Lionsgate, and Ian McShane is expecting to reprise his role for a sixth time.
Ian McShane recently sat down with Dexerto to discuss his return to the franchise in the upcoming From the World of John Wick: Ballerina, starring Ana de Armas. In the build-up to Ballerina's release, which is set between the events of John Wick Chapter 3 and Chapter 4, Reeves' potential return for a fifth film was the big question on every fan's mind. Thankfully, Ian McShane wasted no time in answering it. "Nobody really believes he died," McShane said of John Wick 4's definitive ending.
John Wick 5 has been confirmed to be in development at Lionsgate. However, no other details have been revealed. While the movie is "in development," it doesn't guarantee that the film will ever make it to production and, one day, to theaters. "I don’t know anything about it," the actor continued, addressing his knowledge of John Wick 5. "I mean, that’s it, they announced it and then they’ll make it. It depends on Keanu. If he’s fit and willing, I’m sure they’ll work out a number five."
Ian McShane Created His Character's Backstory With Lance Reddick

The John Wick fandom was dealt a heavy blow in 2023 when it was announced that Lance Reddick, who played The Continental's beloved concierge, Charon, had passed away aged 60. Both Charon and Winston appeared in Peacock's The Continental prequel miniseries. However, like much of the fan base, McShane isn't a fan of the prequel, and disregards the backstory it gave to his character.
Instead, McShane has devised his own backstory for Winston, and it explains how he formed such a close bond with Reddick's Charon. "Usually I’d be with him [Reddick], you know, which was nice, because we invented this backstory between us that they met in Africa in the ‘70s when I was working for MI6 and he was local government," McShane began, continuing:
"They kept in touch… and when they got too old, they got kicked out, and then they formed this partnership in private and formed this relationship… who knows who backed them. That’s the great thing, maybe that’s in John Wick 5, you never know."
While fans wait for John Wick 5 to (hopefully) become a reality, the John Wick universe is giving fans a fresh perspective on its world of underground assassins in Ballerina. The film follows Eve Macarro, an assassin of the Ruska Roma family (to which John Wick also belonged), who seeks revenge for the death of her father. Alongside de Armas and McShane, the film also stars Norman Reedus, and includes a cameo from Keanu Reeves as the iconic assassin who started it all.
Source: Dexerto