Captain Jack Rackham (Toby Schmitz), Black Sails 4.10
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Captain Jack Rackham (Toby Schmitz), Black Sails 4.10

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The name of Captain Flint, though it was strange to me, was well enough known to some there and carried a great weight of terror.
-Robert Louis Stevenson, Treasure Island
Jack Rackham???? Scamming people again?????
Fathoms Deep Host: So you say that Anne is most herself, is most vibrant and alive and fully realized, when she is in battle. What would you say then is Jack's? Is his moment where he is most himself?
Toby Schmitz: I think when he's right out on the edge of anti-authoritarian wheeling and dealing, you know, I think you see it early on with his scene with Gates when he's baiting him emotionally about being an old man. It's really kind of out there tactics. When he does the same with Mapleton. He basically says, 'I'm lying and you know I'm lying. Do you want to come on board?' That's some balls. Stock broker brass balls. You see it, you see it actually time and time again with Jack. And I think that's when he feels the most alive and I think he's addicted to that kind of ballsy 'I can't believe you're actually putting this on the table.'
I think he likes a long shot. And it could be argued a few characters in this show that they bet on a long shot, but I'm not sure they like betting on long shots. I think they do it because they've got nothing else. I think he lives for it.
With Rogers in the last season, he should be in that office, he should really be in there, kind of sucking up to him. If he played his cards right, he could have feasibly had a red coat uniform 48 hours later and still do what he wanted.
Host: Absolutely. I mean, that's what Rogers obviously wanted. But he can't help himself.
Toby: He would far rather do the thing that Rogers wasn't expecting just to see the look on his face.
Host: He was being an ass before he even realized what Rogers was offering him.
Toby: Yeah, he's addicted to being the kid at the back of the class with the snide comment. And still seeing if he can get a way out on top. But I think that's where he comes alive, where he feels the best.
Host: Wow. So he's probably the only character that, I mean, I feel like everyone else is really fighting against that. Everyone else is trying to create situations where they can control.
Toby: Yeah, there's an anarchic streak to Jack. And I think Chaz [Charles] liked it. I think Anne likes it in him.
Host: No, that makes so much sense, why the two of them would be attracted to that.
Toby: Yeah, those two punks find him appealing, I think, because of that. The smarts and the charm and so on, but there's a lot of people with that, I think it's the fact that at the end of the day he's quite happy to put a dagger into someone you didn't think he was going to, or flip the tables completely.
[Source: Fathoms Deep 37]
Toby Schmitz: I mean, [Anne's] an incredible half formed enigma. She more than any other character in the show, in my eyes, needs someone else. I don't think she even wants to stand out alone.
Host: No, it doesn't seem like it at all.
Toby: Where she is her truest self, I think, and is enjoying her own power the most, even more than Charles, is in battle. She's not just holding it amongst the boys. She's holding it amongst every warrior that you can imagine around that part of the equator. She's true and she's powerful and she's turned on and alive and clear eyed and has no doubts, you know.
I remember Clara once saying very early in the shooting, and she stuck to her guns through the whole shoot, she said, 'I don't see it as psychopathic. I don't see it as damaged. But I think that Anne enjoys watching them die when she kills them. She wants to see them slump. She wants to see the blood leak out of them. She likes seeing their breath stop.'
I was like, 'wow, that's dark.'
And she says, 'well you could see it as dark. Just in a really non-theoretical, non-psychological way, she just does that.'
Host: I'm not sure I see that as dark, actually. I see that as more like living in the moment.
Toby: Really visceral, and it's about feelings and touch and things you really can't even put into words.
Host: I mean, it's like the way someone else would really enjoy like a great glass of scotch and watching the sunset.
Toby: That's right. She's a connoisseur of death.
[Source: Fathoms Deep 37]

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Toby Schmitz: The great thing on this show was that the stunt guys and the fight guys, who were just exemplary, they all developed our fighting styles with us. And so if you have a going back for another watch, you watch how Flint has various royal navy moves that have been slightly corrupted. Everyone's got their own style, you know, they made way for the fact that Zach's essentially ambidextrous and learnt on the fly. Well, what they created for Jack was that he's kind of feral and has a few moves that are militarily, you know, ingrained, but have been completely corrupted. And I've got a long reach and I'm really long armed. And so me with a sword, I've actually got a real advantage over people. This is all, you know, subtle, kind of sword fighting nerdy stuff, but it's all character reveal still going on in all the sword fights. Essentially, I think he's got a switch that he can throw, Jack, and it's a kind of, I always imagine it is a real feral, rabid dog, you know. I'm going to slash my way out of the situation. One of those kind of nerds, you push around in the school yard until they snap and you go I wish I hadn't done that, this kid is now foaming at the mouth. [Source: Fathoms Deep 37]
Toby Schmitz: But being ambiguous is actually really easy when you're so emotional because you go, I wasn't really angry that time or I wasn't really upset. That's the great thing about Jack, he's very emotional and is not afraid of screaming in public, weeping in front of his girl, yelling at his boss or his best mate, whereas a lot of other characters really have a lot more masks up and eat a lot of their emotions and bury it in private, you know. And I think it's just a great gift for Jack. If you wear that much on your sleeve, no one can really work out whether it's genuine or not. It's a kind of a get out of jail free, but it's, you know, I think it's good. There's a grain of truth in there.
Host: But you don't feel like it's something that he's doing like with Anne.
Toby: No, no, I think that the way he behaves with Anne, especially in private, is a great insight into who he is. He doesn't mind looking like a fool or weak or emotional because there's always a way to climb out of the hole. And in fact, appearing like the, you know, the odd man out or the more emotional one or the more feminine one or whatever you want to call it is a fantastic gift in this very rugged, macho world. It's allowed him to survive this long....I think it's his main tool and I think the other thing that's helped him survive other than dumb luck and having Charles Vain as an ally is that he is okay with a blade. He's not as good as the other cats in the show who are all masters, you know, but everyone's a killer in the show and he does know how to wield a dagger and he does know how to charm his way into close proximity when suddenly you end up with a knife in your guts. You know, he's not a complete pushover. I think he loves looking like a pushover, but I think the guy knows how to at least thrash his way out of a situation with a blade. [Fathoms Deep 37]
Toby Schmitz: When the script arrived with Jack's backstory in it, I was delighted. And it was completely in sync with my ideas for him, which I definitely kept the creators abreast of. It made sense to me that he was from what we would call now a sort of an aspirational middle class family. And it was all taken away from him. It made sense to me that he was probably one of the more educated kids in town and that he suffered real public shame not only when his father died, but when his father was alive. He's father was a public joke and a drunk, and then pissed away the family business. They seem like really visceral, identifiable things to me....And really everything that I'd made up for Jack and his backstory started a little later than that in his life. I always imagine he was either dragooned or escaped some sort of problem into the Royal Navy. And when they delivered that backstory, I went, well, that's the perfect thing to escape from. You know, for however he got into the Navy and this is still my own imaginings, that seemed like the perfect kind of nightmare to have to skip town for. And the haberdashery, you know, all that makes sense. That was a lovely way of tying into the Calico legend. [Fathoms Deep 37]
Toby Schmitz' ideas for Jack were also published as a comic.