It's the best of times and worst of times for Black Sails' Capt. Flint as Season 2 of the Starz pirate drama begins.

Although the new season begins precisely where the previous one left off — with Flint (Toby Stephens) and the crew of the Walrus staring at a beach covered in Spanish gold from Flint's long-hunted Urca de Lima treasure galleon — Flint doesn't have time to celebrate. Instead, he'll be far more focused on regaining the trust of his men after his lies and murderous deeds in Season 1 led to a mutiny against him.

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"We never wanted the gold to be an answer to end all questions," executive producer Jonathan E. Steinbergtells TVGuide.com. "We wanted it to be the beginning of its own problems. We experienced [Flint] through the eyes of his crew almost exclusively last season — not knowing what he was up to and not knowing where his agenda was coming from. What we wanted to do this season was to get inside his head and to be able to understand much better not just what he was doing, but why he was doing it."

As such, the season features a number of flashbacks to Flint as a young man in London. "Season 2 slowly unpeels Flint and shows the audience where he came from, what is driving him, what the relationship is with Mrs. Barlow (Louise Barnes) — it presents you with a different person," Stephens says. "You're taken on this journey of how this other person became the Flint that we now know. In a way, that's kind of a tragic story." Adds Steinberg: " This season is about him wrestling with the things he's done. Flint is very conflicted about the kind of person he wants to be and questioning the kind of person he's become. A big part of the season is understanding both where he's headed, but, just as importantly, where he came from."


Wherever Flint is headed in the short-term, he will be heading there with an unlikely ally: John Silver (Luke Arnold). "They are both on the outs with their crew and potentially subject to being executed. So, they only have each other to try to get out of that," Steinberg says. "The long arc through the season is about them circling each other, and trying to understand what they are to each and whether they can trust each other. And what happens in a moment where they realize that they can't?"

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And those moments may present themselves more than Flint would like, especially in the early going. "He despises Silver," Stephens says of his character. "He doesn't trust him because he just thinks that Silver is only in it for the short-term money. He thinks of Silver as somebody who literally only thinks a step ahead. If he could, he would either just walk away from Silver or kill him, but he can't afford to."

But the question remains: How exactly will Flint and Silver be able to win over the bloodthirsty crew? "Flint, combined with Silver, has this ability to work the crew politically," Steinberg says. "When Silver and Flint are pulling in the same direction, there's a lot that they can get the crew to do and a lot that they can get them to agree to. Flint is very good at what he does in terms of being able to persuade them that, 'You may mistrust me and you may not like me, but I'm still the best option for you going forward.'"

Regardless of whether Flint regains control of his men, another huge problem lies on the horizon: The English Navy is looking to bring an end to piracy. "A mandate we gave ourselves for the second season was to, in every way, widen the scope of the show," executive producer Robert Levine says. "One of the ways to do that was to take England from something that was spoken about and feared off-screen, and really start to suggest that it's present. It's coming, and it needs to be grappled with."

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That, of course, would have huge ramifications for the not only pirates, but also Eleanor Guthrie (Hannah New) and her entire trade operation in Nassau. As the season begins, however, Eleanor has her hands full with her complicated new partnership with former lover Charles Vane (Zach McGowan). "It felt like they were at such extreme odds in the first season that you never really got to see the pre-existing relationship that was the foundation of it all," Steinberg says. "What we wanted to do in the second season was to give them both solid enough footing that they were able to not constantly be trying to wipe the other one out, and that they were able to engage as equals. They have this very tumultuous relationship. A relationship that's that unstable and that passionate can get very good and it can unravel as well."

But Eleanor will also have to deal with Ned Low (Tadhg Murphy), a violent new pirate who blows into Nassau with no intention of playing by Eleanor's rules. "We went to great effort in Season 1 to make sure that all our pirates had unexpected motivations," Levine says. "There was a place for someone to come in for whom violence wasn't a means to an end — it was the end. Someone that was a slightly more unbalanced in that direction and therefore more unpredictable and more threatening. With Eleanor having taken over this operation from her father, we really wanted to test the limits of just how much control she has over this place when she doesn't have his money behind her. At a moment in which she is short on friends, it forces her to make some very difficult decisions about who the people closest to her are, and how she can survive a situation when she can't quite talk her way out of it."

Ultimately, Flint and Eleanor — and all the characters — have to wrestle with the idea that their world is potentially changing forever. But don't expect them all to let it go without a fight. "The season in some way is about them all grappling with how they see themselves in relation to civilization," Steinberg says. "Some have resolved never to be a part of it, some are questioning whether they can be a part of it, and some desperately want to be a part of it. The season builds to a number of climaxes in which those questions get answered for everyone and in ways that some of them don't quite see coming."

Black Sails premieres Saturday at 9/8c on Starz. Watch the Season 2 trailer below.