So, I watched Skeleton Crew recently that led me down a rabbit hole that’s just about to end with S4 of Black Sails.
Of course the first thing I searched for before making past S1 were figures. I didn’t think there would be anything super official, but was pretty surprised no one attempted any kind of headsculpts for these?!
Other than the two characters I despise (Max and Elenor) I’d pretty much want everyone lol. Flint and Vane for sure!
I see three pathways, potentially
1) Try to get Black Sails ( I loved the show myself) converted into a video game. If it's a wildly popular and immersive video game ( the original actors can come back to do their voices), the odds of figures being made go up dramatically. Still a long shot, but it's a better hope than resting on nostalgia getting to a company so long after the show has finished airing. If Black Sails had a game like Dishonored, with that kind of storytelling, music, visuals and gameplay, you'd increase the fan base for Black Sails exponentially to create the market size you need to justify a figure line.
2) Try to appeal to Todd McFarlane to put it into his Movie Maniacs line. Something like Black Sails is likely more suited, at first glance, for 1/12th. But 1/12th production considers mold/tooling reuse. So it's going to be hard to see one Vane period, much less 3 more variations of him. Again, a long shot. McFarlane has shown, previously, that if he loves an IP, he'll make the figures, even if he knows it's a money loser/bad bet sometimes.
3) Try to appeal to DAM Toys Gangster Kingdom line, and have them build a quasi "homage" figure for the Black Sails concept. They've done soft homage for Pulp Fiction, John Wick, Kill Bill, Machete, Expendables, etc, etc so it's not totally impossible to happen. But that's another stab in the dark.